Sales Reinvented

We at Sales Reinvented are on a mission to change the negative perception of sales people. Each week we will be interviewing experts in the field of sales and sharing their knowledge, ideas and expertise with our listeners. They share with us in our vision of a world where selling is a profession to be proud of. The aim of our formatted show is to provide ‘snackable’ episodes that are short enough to listen to in one sitting but long enough to provide real value that will help you in your sales career. Welcome to the Sales Reinvented Podcast.
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At Sales Reinvented, we are on a mission to change the negative perception of selling. Welcome to the Sales Reinvented Podcast.

Apr 13, 2022

Joe Girard points out that salespeople don’t actively think about their territory sales plan and tend to be more reactive. But companies get held hostage by the best their salespeople can do. Without a plan, you aspire to be the best and just hope it happens. But a company can’t survive on hope. That’s why creating a territory sales plan and executing that plan is key. Hear more of Joe’s thoughts on the strategy in this episode of Sales Reinvented. 

Outline of This Episode

  • [0:45] Why territory sales planning is an underrated activity
  • [1:17] How can territory sales planning improve reactivity?
  • [2:38] Joe’s ideal territory sales plan
  • [3:56] The attributes of a salesperson
  • [6:22] Tools, tactics, or strategies to improve sales planning skills
  • [10:49] Joe’s top 3 territory sales planning dos and don’ts
  • [13:09] Sales success hinges on proper planning 

How can territory sales planning improve reactivity?

Most salespeople are busy getting leads and trying to convert them. But you must take a step back and make a plan. Joe notes that it’s very uncomfortable for salespeople because they feel like they need to be selling. But they need to do more of the right things. How do you spend more time doing the right stuff and less time doing things that won’t make an impact? Focus on high-value activities. 

Joe’s ideal territory sales plan

Joe implores salespeople to use a ranking system. Look at the opportunities you think you should go after (your ICP) and rank who you want to sell to. Then rank the activities you need to do to sell to them. Rank your team's level of ability to do those activities. Then you have to execute that plan. You have to commit to 90 days or six months and see your plan through. Give your team the space to execute the plan and be successful.

But you also have to be adaptable in the trenches. How will everything you do contribute to your plan? You need to make your plan, test it, and come back and revise it as needed. It’s an ever-evolving sales process. You’ll begin to see repeating patterns. Then you can build out best practices and share them with your team. 

Tools, tactics, or strategies to improve sales planning skills

Are you serious about your results? Joe always sets a 90-day plan or sprint. Then he breaks it down into activities and holds himself accountable to those activities. Implementing a 90-day sprint helps you focus. 

Secondly, if you’re trying to figure out how to help new customers, talk to old or current customers. How did your service or product help them? Validate your assumptions and build in a feedback loop. Get the customer language into your sales language.

Make the time to plan and review your work. Even something as simple as looking at your daily activities. Did you miss something? Write it down and make a plan for the next day. Then review the week and make sure you didn’t miss anything. If you did, knock it out and close out the week.

Joe notes that there’s no shortage of training and tactics and it can be overwhelming. He emphasizes that it’s not about what you can put into salespeople, it’s about what you can pull out of them. Territory sales planning should be about making the most of each individual and helping them shine. 

Sales success hinges on proper planning 

When Joe started in sales, he wasn’t doing well. His boss told him that if he didn’t pick things up in the next 60 days, he wouldn’t make it. The other rep working with Joe gave up and went to work for the competition. They were sitting at $2.3 million between the two of them. Joe put a plan together—based on him being the sole salesperson—to reach sales of $4 million. Joe was told that if he didn’t hit his target, he wouldn’t get paid. He had to almost double his current sales. 

So he broke down what his activities would need to look like monthly, weekly, and daily. He looked at how many people he needed to have on his list, how many he needed to talk to, and how many appointments he needed to book. You have to break things down to what needs to happen every day to stay on track. You can’t make up for lost weeks and months. By the end of the year, Joe hit his target and surpassed it—landing at $4.1 million. He didn’t work harder but made the most of his time with a clear plan.

Low-level salesmen who make plans can outperform the highest performers if they build a good plan and execute it day after day. It’s all about execution. Don't wait for someone else to tell you how to plan your territory and above all—don’t give up.

Connect with Joe Girard

Connect With Paul Watts 


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Apr 6, 2022

Wes Schaeffer states that his purpose in life is to rehabilitate salespeople and train their managers. Most managers are hired from within because they were successful. They were successful because they were hungry, aggressive, and impatient—not necessarily because they were the smartest or most detail-oriented salespeople. Those attributes are at odds with the management role. Those skills can harm them because they are aggressive and impatient with their team. 

They’re putting pressure on their salespeople but don’t have the skills to teach them. Salespeople are left on their own to make it or break it. Territory planning isn’t taught. If it is, it’s taught from a book—not from someone who did it successfully. So how do you change that? Find out from Wes in this episode of Sales Reinvented.

Outline of This Episode

  • [1:08] Why territory sales planning is underrated by salespeople
  • [2:43] How to reduce reactivity with territory sales planning
  • [5:13] Wes’s ideal territory sales plan
  • [8:08] Wes’s version of the ABCs
  • [10:38] Why you need to just start writing
  • [13:50] Top three sales planning dos and don’ts
  • [18:01] How to take control of your territory

How to reduce reactivity with territory sales planning

Most people are reactive to everything in their lives—it’s not even necessarily a sales problem. The type of people that are drawn into sales are outgoing “people’s people.” They’re not engineers or accountants but simply good at making friends. Their personality is not methodical and goal-oriented. They're relationship-oriented. Now, they’re being asked to plan. 

Wes wrote “The Seven Deadly Sins of Selling.” The first sin is shooting from the hip i.e. winging it. Most salespeople have been hired as a cultural fit. A sales manager probably isn’t detail-oriented or has a methodical process for hiring and onboarding. There isn’t a culture built around territory planning. 

Wes’s ideal territory sales plan

Wes instructs managers to manage activities and pay on results. Just like losing weight, closing a sale is a lagging indicator. If you want to lose 10 kilos in 90 days, stepping on the scale at 90 days only proves how diligent you were at following the process. What did you eat for every meal? How did you exercise? Maybe you hired a fitness coach or a dietician. Maybe you have a tracking app, planned your meals, and planned when to exercise and how much. If you’re diligent for 90 days, you’ll hit your goals. 

Sales managers don’t give salespeople the activities to do. Wes tells people to batch phone calls: before breakfast, during lunch, and at the end of the day to get around gatekeepers. He has different scripts for each call. They’re telling a story through multimedia and different steps. Wes gives his community a way to track their time in 15-minute increments. Whatever you measure, you can improve. Break your big plans down into 15-minute increments, i.e. what you have to accomplish to reach your lofty goals. When you are diligent with this, you’re more likely to be successful. 

The characteristics a salesperson should have

Wes emphasizes that the mantra “Always be closing” is crap. This idea was propagated when people the age of our grandfathers were in sales. Yet we still live by the adage. Wes’s version of the ABCs is “Always be curious. Always be courteous. Always be concise.” Ask more questions. Take a step back and ask, “Where are you a product fit? Why do people buy your stuff? What pain do you solve?” Start there. Where do these people congregate? 

Wes was working for a startup in Austin, TX. The technology was beneficial in the healthcare space. Wes looked at technology in healthcare and there was a huge community with state and regional chapters. He joined those chapters and became active in those communities. He went where the fish were. You can’t just go to the local swimming pool and drop a pole in the water because it’s convenient. 

Tools, tactics, and strategies Wes embraces

Wes gives out a free guide called “Process Before Login.” The concept is that you need to document your steps and track your activities before you log in to any tool. Because a tool won’t save you. You know what your territory is. You have to figure out how to get in front of people. Can you knock on their door or go to events where they congregate? Once you plan daily and weekly activities, you can manage them. How many phone calls can you make? How many emails can you send? How many handwritten letters can you write? Do you have scripts for text messages? How are you engaging people on social media? 

If you're in B2B, LinkedIn can be good. But Wes gets more crappy messages on LinkedIn than anywhere else. Why? Because people don’t know how to communicate. People are spending money to get in front of Wes with an awful message. Learn how to communicate. Blog. Write a post for LinkedIn. It can even be a FAQ post. Prepare written answers to objections ahead of time and link it to a blog or LinkedIn post you’ve written. Your prospect will be impressed. They’ll think you know what you’re talking about. If you do anything, Wes implores you to just start writing. Write a daily article for LinkedIn that your prospects would be interested in. Your life will change in 30 days. 

What are Wes’s three sales planning dos and don’ts? Listen to find out—they might really surprise you.

How do you take control of your territory? How do you disqualify a prospect to focus on the important accounts? Listen to hear Wes’s process!

Resources & People Mentioned

Connect with Wes Schaeffer

Connect With Paul Watts 


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Mar 30, 2022

Jeff Bajorek believes that salespeople underrate territory sales planning because it’s boring—and they lack a growth mindset. But if you’re a full-cycle sales rep, you need to know where your revenue is coming from. So you need a good grasp of your territory, the players in it, and who’s moving in and out of it. You need a handle on price increases and must know your products inside and out. It’s not all buying dinners and playing golf with prospects. Territory sales planning is where many people could make up ground if they do the work

Outline of This Episode

  • [0:59] Why salespeople underrate territory sales planning
  • [2:08] How territory sales planning can lessen reactivity
  • [3:52] The ingredients for the ideal territory sales plan
  • [7:34] The attributes that make a salesperson successful
  • [9:25] Tools, tactics, or strategies to improve territory sales planning
  • [11:12] Jeff’s top “do”: Embrace the buddy system
  • [15:12] Jeff's simply and effective territory planning strategy

How territory sales planning can lessen reactivity

Do you want to be at the whim of your territory? Or do you want to have an impact and influence on what your territory produces (from a revenue perspective)? If you’re waiting for a customer to wave their arms in the air, you’ll be waiting a long time—and doing activities that won’t move the needle. Can your calendar be used against you in a court of law to convict you of being a salesperson? 

Do you have time blocked to prospect? Do you have time blocked to contact your regular customers? Do you have time blocked to research and develop accounts in your territory? Or are you completely winging it? Are you taking control—or waiting for things to happen? Jeff points out that you know what the right answer is but you’re probably still not doing enough of it. 

The ideal territory sales plan is focused on a growth mindset

Who are the players in your territory? Who is growable? There are a lot of companies talking about fresh opportunities but “new” versus “old” is the wrong paradigm. Growable versus not growable is what you need to focus on and accessibility is the issue. Jeff breaks things down into quadrants: growability and accessibility.

  1. Quadrant one is those that are growable and accessible. These are new or existing accounts with room to pick up wallet share.
  2. Quadrant two is growable but not accessible. These are dream clients you have to work to gain access to.
  3. Quadrant three is not growable but accessible. These are the clients that shake your hand, slap you on the back, and say “It’s good to see ya” but there’s no room to grow.

You feel productive when you gain the attention of quadrant three. If you can’t grow them, they’re the best source for referrals or introductions. Use them for market research to help you gain access to clients in quadrant two.

But people spend so much time in quadrant three. They could spend half the amount of time maintaining business and spend it gaining access to new accounts. Where are you spending your time? Spend it all in quadrant one if you can. Once you fill that demand, you’ll have a void. You need to make inaccessible opportunities in quadrant two more accessible. Then, use your best customers to understand what it takes to gain access—whether introductions or referrals. Now you’re selling. 

Tools, tactics, or strategies to improve territory sales planning

Every year, you start from square one. Your company likely asks for 7%. Every January, Jeff went to a national sales meeting. They’d get information about fee increases, new products, line extensions, etc. Jeff had his notebook open and a pen in his hand. He took diligent notes and knew exactly who he’d call on with new products. By the time he left that weekend, he’d have his territory sales plan sketched out. He knew who to call, who would be a great target, who would buy, who was already using similar products and how much they were using, and the value of each customer. He left those meetings fired up and set appointments for the next week. 

Jeff points out that pen and paper is an under-utilized tool. You don’t need fancy technology to plan your territory—you just need to set aside time to do the work. Opportunities won’t fall in your lap. Where do you have good access and growability? Write it down. Who are your dream clients? Who are a great fit and you just don’t know? Write it down. How do you plan to reach them? Who are your rockstar clients? Write it down. That can translate to introductions and referrals. You need to understand the players in your territory before you can do anything else. 

Jeff’s territory sales planning do: Embrace the buddy system

Find a buddy. Jeff worked with another salesperson and they got together once a quarter. They met in the middle and planned for the next quarter. They held each other accountable. Every quarter, they presented what they accomplished, what their revenue looked like, how they executed against their plan, and how successful they were. It’s tremendously beneficial. If you don’t have leadership that will hold you accountable, find a buddy—in or outside of your organization.

The bottom line is that sales is a verb. You have to act on your plan. You can’t afford to sit and wait for sales to happen. Create opportunities, steward them to close business, and maintain those relationships to earn referrals.

Connect with Jeff Bajorek

  • Connect on LinkedIn
  • Email Jeff at JF(at)

Connect With Paul Watts 


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Mar 23, 2022

Too many salespeople wing it. They just wanna “See what’s out there.” But Mark Hunter emphasizes that planning is the only way you’ll maximize the opportunities in your territory. You can’t react to whatever business is out there. 

Mark loves to say, “Tomorrow begins today.” You have to plan your day, week, and month. Why? It allows you to use your time efficiently. Many salespeople are busy but not as productive as they could be if they had planned how they’d use their time. Listen to this episode of Sales Reinvented to hear Mark share more about his planning process!

Outline of This Episode

  • [0:49] Why is territory sales planning underrated? 
  • [1:13] How territory sales planning can reduce reactivity
  • [2:06] The ingredients of the ideal territory sales plan
  • [3:39] Attributes and characteristics that make a salesperson great
  • [6:33] Tools, tactics, and strategies to improve sales planning skills
  • [9:17] Mark’s top territory sales planning dos and don’ts
  • [12:36] Control your territory—don’t let your territory control you

The ingredients of the ideal territory sales plan

The first question you must ask is who is your ideal customer? No matter the size of your territory, there will always be opportunities. You want to focus your time on the best of the best. If you don’t know your ICP, you’ll waste a tremendous amount of your time on other people.

You have to understand the outcome that you can create. No customer buys anything. They invest. They invest because they want a return on their investment. So what can you help them achieve?

Don't overlook the value of your calendar. Block time to work on projects. Mark follows the “10 am Rule.” By 10 am, he wants to have accomplished something significant. If you can do that, it motivates you. If the day were to fall apart you could still consider it successful. By mid-morning, Mark had already sent out a major proposal to a client. What has it resulted in? He’s accomplished so much more. 

Attributes and characteristics that make a salesperson great

Your head needs to be in the right place. You have to focus on using your time efficiently—while helping customers—and never be satisfied with where you are today. Mark points out that it’s not his job as a sales manager to motivate his salespeople. His goal is to create an environment for them to motivate themselves. There are a few things Mark shares that lead to success:

  • You have to understand the value of time and how you manage it. Everyone is blessed with 24 hours a day. How will you choose to use them?
  • Be customer-focused. Salespeople set a monetary goal not realizing that’s the reward, not the goal. Your goal should be meetings, making customers happy, and helping customers achieve their outcomes.
  • Never be content with where you’re at. Success can only be defined by yourself. Don’t let others define it for you. You can deem yourself successful while never being satisfied. Why? Because you’re always asking what you can do to become better. 

How can you become more proficient? How can you be more productive? The measure of productivity is the results your customers achieve from the outcomes they’re able to achieve based on how you’ve helped them.

Top territory sales planning dos and don’ts

Mark shares some things you should—and shouldn’t do—to achieve your goals:

  • Identify your ICP and develop key questions that focus on each ICP.
  • Manage your time. Break it up into segments. Allocate a percentage of each day to small, medium, and large accounts. 
  • Understand where your greatest opportunities are and manage your pipeline. It doesn’t matter how many leads go into the top of the funnel—it’s what you pull out through the bottom. Identify and qualify prospects quickly to close them faster. 
  • Don’t hang on to customers that aren’t profitable. You can’t afford to keep them. Always look to trim the bottom 10% of your client list.
  • You are not in the customer service game. The sales role is about creating incremental opportunities. Don’t allow yourself to play customer service agent. 
  • Don’t allow yourself to associate with anyone who is not going to be a positive influence on you. You are the sum of the 5 people you associate with the most. Invest your time with really smart people. 

Control your territory—don’t let your territory control you

Mark was young and enthusiastic when he started in sales. He had a large territory assigned to him. He soon realized that territory included demanding customers. He felt he had to step up and deliver them more service. The result? He could leave their office and they’d call 20 minutes later and ask for something else. 

He had been working the territory for 3 months when his boss asked him to meet for breakfast. Mark was an hour and a half late because he was visiting a customer taking care of a problem. He thought his boss would be happy. His boss was actually livid and threatened to fire him on the spot. It wasn’t because he was let. It was because he allowed his priorities to get disrupted. He was allowing problem accounts to control how he operated his territory. It’s one of the worst problems new salespeople have: the desire to want to serve and please everyone out there. 

Mark’s boss told him that he would never be able to satisfy every demanding customer. Instead, the objective is to minimize them. Allow them a small percentage of your time. If not, you’ll never have time to develop customers to create the incremental business you need to meet your numbers. Failure to make your number will get you fired in a quarter. 

Resources & People Mentioned

Connect with Mark Hunter

Connect With Paul Watts 


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Mar 16, 2022

There are actions, tasks, and disciplines that must be accomplished to create a perpetual business. Tom Ninness points out that it’s important to know what activities drive your business. When Tom first entered the mortgage industry he was assigned to a territory. He knew that to use his time wisely, he needed a plan. So he planned where he would go when. So much so that all of his customers knew which days he was coming to visit. What else does Tom do to support his territory planning? Learn more in this episode of Sales Reinvented.

Outline of This Episode

  • [1:11] Why is territory sales planning underrated? 
  • [2:39] How territory sales planning can reduce reactivity
  • [4:15] The ingredients of the perfect territory sales plan
  • [5:45] Attributes and characteristics that make a salesperson great
  • [7:57] Tools, tactics, and strategies to improve sales planning skills
  • [10:19] Top 3 territory sales planning dos and don’ts
  • [14:07] Be servant-minded with your approach

The ingredients of the perfect territory sales plan

If you have a plan laid out so you know what you’re doing hour by hour, you’ll get a great ROI. Tom has the loan officers he works with complete an exercise to calculate their hourly rate. If they want to make $250,000 and want a week off every quarter. They have to work 40 effective hours a week. That averages $130 an hour. Are the sales folks completing value-based activities that will earn them $130 an hour? When you place a value on your time it makes the necessity of a plan even more apparent. And, it will help you be more successful.

Attributes and characteristics that make a salesperson great

A salesperson has to be likable and servant-minded. People will want to do business with you. Many salespeople view selling as something they do “to” another person instead of something they do “for” another person. Tom firmly believes that he “gets” because he gives without expectation of anything in return.

Tim Sanders wrote a book, “Love Is the Killer App,” in which he posits that business people are looking for knowledge. Your knowledge is worthless if you don’t share it. Secondly, you have to have a network to share it with. The larger your network, the greater your opportunities. Lastly, give with no strings attached. That’s where the law of reciprocity kicks in. 

Tools, tactics, and strategies to improve sales planning skills 

Salespeople can do business with friends, family, and coworkers. But there are other people in your network. Tom’s end customer has friends, families, and coworkers. They can refer business to him. If he does a great job and a happy customer fills out a survey for him, he believes there are at least four more opportunities for him to do additional business.

So how do you get these names? Tom uses a form where he asks happy clients for a list of professionals in their circle of influence. They gladly provide that to him. He can then share the survey they’ve completed with that list and cultivate appointments. When you delight your customers, they’ll want to refer you to their friends and colleagues.

Be servant-minded with your approach

Tom represents the financing for a builder. Someone else that represents a builder wanted to buy a unit from Tom’s builder but wanted to use his own lender. Tom’s builder flat out told him no—he had to work with Tom or he wouldn’t sell the property to him. The builder warned Tom that the customer was upset and to be mindful of that when they spoke.

Tom gave him a call and asked him to call his lender to see what they’d offer him. He agreed to match it. Tom had Googled him and done some research and really liked this guy. So throughout the next year, he sent him information and resources and gave him ideas. Tom always asks people, “What is the biggest challenge you’re having in your business?” The answer is usually something they’re having problems with. After a year and a half of offering value to this guy, Tom gets a call from him, asking him out to lunch.

After the waiter took their order, he said “Tom, I feel like I’m having an affair.” Dumbfounded, Tom said “What?!” Tom had given him so much value while the lender he had worked with for 20 years wasn’t motivated to help him. This man landed a new builder with 55 townhomes and made Tom his new lender. Tom emphasizes that just because you hear the word “no” doesn’t mean you give up. You can give someone value with no strings attached. Don’t be surprised if it comes back to you tenfold. 

Resources & People Mentioned

Connect with Tom Ninness 

Connect With Paul Watts 


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Mar 9, 2022
Territory sales planning is like building a house. To be successful, you need blueprints. You need a plan to follow so you can build a firm foundation. Lisa firmly believes that you need to create a plan, work your plan, and take responsibility for exceeding your sales goals. Lisa shares her ingredients for the ideal territory sales plan in this episode of Sales Reinvented. 

Outline of This Episode

  • [0:55] Why is territory sales planning underrated? 
  • [1:33] How territory sales planning can reduce reactivity
  • [3:00] The ingredient of Lisa’s ideal territory sales plan
  • [6:41] The attributes of a great salesperson
  • [8:33] Tools, tactics, and strategies to improve your skills
  • [9:49] Top 3 territory sales planning dos and don’ts
  • [12:09] Forecasting is the key to successful territory sales plans

How territory sales planning can reduce reactivity

At the beginning of a year or quarter, you must take the opportunity to evaluate your territory. How effectively are you using their time? Where are the dollars gonna come from? A simple spreadsheet of your sales reports for the past 2–3 years will help you realize there’s gold within your territory. You don’t have to spend time doing more prospecting. Why? You can fish in your own territory.

The ingredient of Lisa’s ideal territory sales plan

Lisa believes that there’s not a perfect sales territory plan—it must always evolve. This is her general recipe for success:

  1. Run a client analysis: Run a report that shows your clients and all of the sales for the last 2–3 years to see an average. Where are the dollars coming from? How much time are you spending on your different accounts? This will help you create a territory sales plan that will help you achieve your goals. 
  2. Complete a detailed forecast: How many dollars has an account given you in the last five years? Sort your accounts from the highest to the lowest. What dollars do you anticipate you can do with each client? Look at overall revenue and how you can expand it. What services or products are they buying from you? What else could they buy from you? The most effective way to grow your business is cross-selling with current clients. 
  3. Validate information directly with your client: What are their goals, initiatives, and priorities? What could you sell them? Are they expecting the same inventory? What are they anticipating to purchase from you? Get answers directly from your key accounts. 

Most salespeople put together a territory plan and shelve it. To be successful, you must review it monthly and quarterly. Forecast a number and lock it in. Challenge yourself to meet your working forecast. It will help you validate how accurate your forecasts are at the beginning of your territory planning. 

Forecasting is the key to successful territory sales plans

Lisa and her Director of Sales worked together to dive into and conquer their territory sales plan. When they did a thorough forecast—based on the previous 4 years—they realized that 92% of their business would come from existing customers. Some of them didn’t buy from them in 2020 because of COVID. That showed that they could reignite old client relationships. It helped direct their prospecting. 

This exercise also helped the sales team gain clarity on who is responsible for what—especially when dividing up an existing plan. It’s a team effort to get business and create their next best year ever. A sales professional will create and work a plan and reinvent themselves as a trusted advisor because they know the value they can bring to their clients. 

Connect with Lisa Leitch

Connect With Paul Watts 


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Mar 2, 2022

The top-performing salespeople understand the importance of territory sales planning. They know that if they create a plan and work the plan they’ll outperform their peers. But John Smibert believes that a strategic plan applying the 80/20 rule is. He fleshes out what that could look like in this episode of the Sales Reinvented podcast! 

Outline of This Episode

  • [1:05] Why planning is an underrated activity
  • [2:25] Stop being reactive and create a plan
  • [3:55] John’s ideal territory sales plan
  • [6:50] The right mindset is key to success
  • [7:53] Tools, tactics, or strategies to improve
  • [9:40] John’s territory sales planning dos and don’ts
  • [12:42] Match your domain expertise with your ideal customer 

The ideal territory sales plan

It’s no secret that the top salespeople are great planners. They routinely run a SWOT analysis and look at their strengths, weaknesses, opportunities, and threats. It’s a key strategic planning tool. You also need to identify your target and objective. Your company may give you an objective but you’re the boss of your own business. You certainly need to plan for what your company expects from you but why not shoot for more? 

Put the quota aside. What do you need to do to achieve your objective? Then look at your territory—identify where opportunities are likely to be. What 20% of accounts will get you 80% of the value? Secondly, look at your ICP. Who are they? Do some research, identify them, and focus activity on them alone. If you don’t have a plan you grab onto the first opportunities that come your way. You’ll find that you’ve filled your pipeline with average opportunities at best. 

John’s territory sales planning dos and don’ts

John hears a lot of sales managers complain that they don’t see the right level of activity from their salespeople. But if their salespeople have a plan in place that has been thought through strategically, less activity is sometimes good. But John nails down some dos and don'ts that can help you focus in the right place. 

  • Set aside the time to create a detailed territory plan once a year. The annual plan needs to be broken down into quarterly, monthly, and weekly goals. You need to wake up every day and say, “What do I need to do to progress my plan?” 
  • Know where you’ll get the best results and focus on them. Focusing on the right 20% will get you 80% of the results. 
  • Review, review, review. How do you stay on plan? What do you need to do?
  • Don’t create a plan and forget about it. You’ve created it to help you stay on track to reach your goals. 
  • Don’t assume every customer is the same. Market segmentation and account targeting around your expertise is important. Everyone has domain expertise, so focus on customers who value what you have to bring to the table.

Learn how to say no. You don’t want to chase every opportunity that comes through the door. The top salespeople say no far more than yes because they know where the value is. 

Match your domain expertise with your ideal customer 

John recently co-authored a book called “The Wentworth Prospect” about a young lady who progressed well in her sales career with the help of a coach. It’s based on a true story about a woman John actually coached. This woman—named Sue—was selling cybersecurity solutions. She had learned the product well and had studied cybersecurity in university, so she had developed some domain expertise. 

John asked her where she wanted to focus her territory. She stated her goal was to approach mid-level organizations but that she didn’t have an industry chosen. So they did some research and landed on a focus in the banking and finance industry. Why? She had a background in banking. She knew she had a unique perspective to bring to the table, her product fit well, and they were an ideal customer. 

In that year, because she eliminated 80% of her territory and focused on the 20%, she blew her quota out of the water. All because she created a plan that she followed diligently. 

Resources & People Mentioned

Connect with John Smibert

Connect With Paul Watts 


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Feb 23, 2022
Carrie Millen jokes that sales territory planning is underrated because it’s spelled “W-O-R-K.” It is “something my boss told me I have to do.” It feels like any time invested in territory sales planning cuts into sales time. Why would they bother doing the work? It seems like busywork over an investment. But that’s exactly what it is—an investment. But the right data-driven sales plan is an investment that will pay off. Carrie explains why in this episode of Sales Reinvented!

Outline of This Episode

  • [0:44] Why is sales territory planning underrated? 
  • [1:38] How to stop being a solely reactive salesperson
  • [2:30] Carrie’s data-driven sales territory plan
  • [4:31] The attributes that make a salesperson great at sales planning
  • [5:41] The tool, tactics, and strategies Carrie implements to stay on course
  • [8:10] Carrie’s top 3 territory sales planning dos and don’ts
  • [11:45] Where sales territory planning can lead

Carrie’s data-driven sales territory plan

Territory sales planning not only provides a guideline but it helps take the thinking out of sales. How? If you have a plan, know it, and work it, you’ll be able to execute sales efficiently. If you spend 59 minutes planning and one minute executing your plan, you’ll likely have more success (Carrie’s nod to Albert Einstein). 

While your plan does depend on what you’re selling and where you’re selling it, data is key. What is the size of your territory? Size of an average sale? Size of the clients you’re selling to? 

Creating profitability and long-term value with a client is a major factor. If you are investing your time and effort, you want to build a long-term relationship with that client to continue hitting your numbers. You can’t just focus on whales but must balance with some smaller fish. 

The tool, tactics, and strategies Carrie implements to stay on course

Carrie notes that there’s a balance between quick fixes and overall planning. Sales is like being on a dodgeball court—balls are being thrown at you from all angles. You don’t always have time to think and simply have to react. But to react with the proper response, you have to be well-prepared. You need to be intentional about what your day-to-day activity is.

Carrie posts the key things she wants to focus on throughout a quarter as the screensaver of her computer monitor. It makes it easy to quickly refocus her activities and stay on track. She owns the plan that she’s made whenever she veers off track. However you prefer to do it, book intentional time in your day to focus on the plan that you've built. 

Secondly, if you’ve built a plan for the next 12 months, how do you know you’re on track? You need data. You need to test and measure that data. If you estimate that you’ll have a certain number in your pipeline by a certain date, measure it. Where are you at? What activities are driving the people in your pipeline?

Carrie loves the Eisenhower Matrix. What is important? What is urgent? What isn’t important or urgent? A territory plan will allow you to navigate what’s urgent and what isn’t. Your wins need to be meaningful and help you achieve the goals of your plan. 

Carrie’s territory sales planning dos and don’ts

Carrie shares a set of dos and don’ts that she uses to stay on course and organized. 

  • Start small and pick a segment and a plan and consistently evaluate it. Then hone in on one small bite of your plan at a time. 
  • Make friends with someone who is financially minded or analytical and have them in your back pocket. Humans are not meant to do everything by themselves.
  • Use blinders. Stay focused on the territory plan in front of you. Work the plan.
  • To do this, create a simple criteria framework that proves you’re on the plan. When do you know if someone is part of the overall plan? You don’t want to accept a client unless they fit in your plan. 
  • Don’t borrow someone else's plan or use last year’s. You couldn’t cheat in school, why do it now? 
  • Don’t work in a vacuum. Get some feedback. Ask your clients why they chose your product or service. 
  • Don’t put all your eggs in one basket. Go after multiple industries and types of clients that fit your product/service. If the travel industry was your only focus, you’d likely have been out of a job in 2020/2021.

Where sales territory planning can lead

Carrie was coaching someone to help her develop her sales skills and territory planning. This person works at a fast-growing SaaS company that was looking to branch into different niches. She wanted to build a plan for herself to grow the new segment. She approached her leadership with the idea to use new assets. She saw a challenge that could be fixed that could lead to exponential growth. 

Her plan caught the eye of the VP. He asked her to implement her plan for every team. Soon after, she was promoted to a role as a Sales Manager. It was all because she applied the skills she’d learned. She looked at the problems in front of her and took ownership. It had a cascading impact on her business.

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Feb 16, 2022
The most successful salespeople have the discipline to do what will deliver success. And territory sales planning is a critical component of that success. Most salespeople don’t see the benefits of sales planning, so they don’t do it. Salespeople underrate territory planning because they’re focused on short-term calendar-focused targets. They’re highly reactive. 

Today’s guest, Wayne Moloney, shares that the average tenure of a B2B salesperson is only 16 months and it’s steadily decreasing. He believes that having the right territory sales plan in place can lead to long-term success, growth, and longevity in the profession. In this episode of Sales Reinvented, Wayne shares how salespeople can transform their plans with some simple questions. 

Outline of This Episode

  • [1:01] The largest reasons salespeople discount sales planning
  • [3:20] How to overcome reactivity with territory sales planning
  • [5:17] The ingredients for the perfect territory sales plan
  • [7:53] Attributes or characteristics that make a salesperson great 
  • [10:48] A simple territory sales plan is the key to success
  • [14:10] Top 3 territory sales planning dos and don’ts
  • [16:17] How a simple plan led to global sales success

How to overcome reactivity with territory sales planning

If you’re planning a territory, you’re clarifying and articulating where you want to go and what roads will lead to them. If you’re reactive, you’re reacting to suspects, not the right type of customers. Territory planning helps you target the right customers, establish goals for income, and ensures sales growth over time. It also helps you engage with customers early enough in the sales process to have an impact. 

A good sales plan defines the specific industries and sectors that will offer the most opportunity to you—and why. That’s the foundation of any plan. Then you must look at the characteristics of your high-value clients. That helps you identify your ICP. Focus on the organizations you can best help versus those looking for a white paper offered by your marketing teams. A good salesperson also completes a comprehensive competitive analysis (i.e. what your competitors are doing and why they’re doing it). 

Attributes or characteristics that make a salesperson great 

Accountability is critical. After 40+ in sales and business management, Wayne still has a mentor that he shares his goals with who helps hold him accountable. It’s critical to Wayne’s success and will be to yours, too. Accountability means taking responsibility for your plan and the actions you take. Another critical component? Set goals and write them down. Wayne emphasizes that “A plan that’s not written down is just a thought.” You must define and implement actions to make things happen. 

Great salespeople don’t operate as islands. Wayne worked with someone who got a group of people together and asked them to pull apart and critique his plan to strengthen his approach. One of the biggest opportunities for salespeople is achieving domain expertise. Developing this starts by knowing what businesses to focus on. You can’t be all things to all people. You need to understand and know your addressable market. 

A simple territory sales plan is the key to success

Wayne shares some simple yet strategic questions you can ask yourself to build a successful territory sales plan: 

  • Where are you now? Why are you where you are? Walk back through what’s happened with your territory, your best and worst clients, and even those you’ve lost.
  • Where do you want to be and when do you want to be there? This gives you a starting line and a finish line. The middle is the gap that will grow your territory.
  • What resources will you need? What tools do you have available to aid your planning?
  • How will you measure performance? When and how will you review your progress? When are you going to do it? How are you going to do it? Who will you involve in the process? 

Walking through these questions is the easiest way to build a plan that’s simple, easy to understand, and helps drive you to success. 

What are Wayne’s top three territory sales planning dos and don’ts? Listen to find out!

How a simple plan led to global sales success

A man Wayne calls “Jim” used to work for him. Jim was very successful in his sales position but didn’t know why. He was always reluctant to make a plan. Because he was so successful, it was hard for Wayne to argue why he should build a plan. He still taught him the proper framework but never truly enforced it. 

Jim moved on and took a role with a major credit card company. One day, Jim called Wayne and thanked him. Why? Because Jim struggled in the credit card industry. So he sat back and went through Wayne’s planning process. He became the top salesperson in his organization. He closed the two biggest global opportunities because he knew where to focus his territory plan. 

As a sales manager, whatever you teach your team is not wasted if you coach them properly. Wayne’s message to salespeople? Don’t dismiss what you’re taught—it will become useful at some point in your career. 

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Feb 9, 2022
We live in a noisy world where it’s hard to focus. But you can manage your territories better with great territory planning. If you’re a salesperson in the field every day, proper route planning can be a gamechanger. The right tool not only helps you plan the most efficient route but also helps you prioritize your sales calls in any way you see fit—annual spend, important relationships, and more. Steve Benson joins Paul in this episode to talk about his revolutionary route planning too, Badger Maps. 

Outline of This Episode

  • [0:46] Territory sales planning: underrated by salespeople?
  • [1:27] Sales territory planning can reduce reactive sales activities
  • [2:28] The ingredients of the ideal territory sales plan
  • [3:54] Attributes and characteristics of a great salesperson
  • [5:57] Tools + tactics + strategies to improve sales planning skills
  • [8:20] What Badger mapping offers field-based people
  • [11:32] Top 3 territory sales planning dos and don’ts 
  • [14:42] The right tool boosts effectiveness enormously

The ingredients of the ideal territory sales plan

It’s important to take your actual territory into account when you make a plan for your territory. You want to figure out how to plan your day in a way that hits the most important customers efficiently. You need to be organized and gather data so you can prioritize in the first place. 

Some people are more organized by nature. Likewise, some people—and cultures—have a better grasp of geography than others. Some people can visualize things and use mapping or routing tools. Those that struggle with geography—and even those that are skilled—can benefit from tools like Badger Maps.

Paul covered the NE part of England when he first started in sales. His trunk was full of maps and he’d use 4–5 every single day. At the time, you had to master driving with one hand and navigating with a map in the other. He wished he had access to a tool like Bader Maps. So what can it do for you?

What Badger mapping offers field-based people

Steve was a geography major in college. He, too, used paper maps. But as mapping tools came out, he realized that sales territory planning was a problem that could be solved with technology and mobile devices. Bader Maps combines the ability to connect their customer’s data (i.e. in their CRM) into a mapping environment. It helps them see their field and determine who to prioritize as a customer (spending can be color-coded, as one example). 

It shows them where appointments are already set and helps them optimize a route based on priority. The app allows you to map out your sales territory in minutes—not hours. The algorithm behind building a route is heavy math that can't be done in your head. Badger takes mapping a territory, prioritization, and route-planning to a whole new level. It also allows you to change your route on the fly and adjust your day to prioritize high-value customers when necessary. 

Top 3 territory sales planning dos and don’ts 

Steve follows these simple—yet effective—when route planning for a sales territory.

  • Take the time to get organized. 
  • Leverage tools to be efficient; don’t design sales territories by hand.
  • Enjoy the strategizing. If you’re in the right headspace it can be fun! 
  • Don’t do it by hand (using google maps, a calendar, and CRM). 
  • Don’t blow things off.
  • Don’t strategize alone, keep your team (including management) in the loop. They can help you brainstorm and improve. 

Listen to the whole episode for more of Steve’s tricks of the trade. 

The right tool boosts effectiveness

Steve works with a company with 300 sales reps. Each one of them manages 10 partner relationships with dentists. But many of them were competing for the same dentists. Their data was a mess. So Steve helped them connect Badger with their CRM. They organized their customers, guided them in the right direction, and their sales jumped 15%. They calculated their miles and meetings throughout the process. Their miles decreased 20% and weekly meetings increased 25%. When the whole company uses the product, the results can be astounding. 

It’s worth spending your time on route planning for your territory using the right tools. You’ll drive fewer miles and bump your sales in a meaningful way. Learn more about Badger Maps in this episode of Sales Reinvented!

Resources & People Mentioned

Connect with Steve Benson

Connect With Paul Watts 


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Feb 2, 2022

The best way to stop being reactive is to ask how you can make your targets while doing as little work as possible. What activities are important? What things can you do to make every minute as useful as possible? It starts by knowing your territory and your plan for your territory. Then you must employ some creative laziness. Learn more about Steve's unique strategy in this episode of Sales Reinvented.

Outline of This Episode

  • [0:47] Why is territory planning an underrated activity?
  • [2:38] How territory planning can help you be more organized
  • [3:33] Steve’s ideal territory sales plan
  • [4:47] Great salespeople need to be creatively lazy 
  • [7:35] Tools, strategies, and tactics to improve sales planning 
  • [8:30] Top three territory sales planning dos and don’ts 
  • [10:07] Focus on your niche in your geographical area

Steve’s ideal territory sales plan

A territory can mean many things to many people. Usually, it’s a geographic territory. Most salespeople believe the bigger the territory the better. Steve says that’s a lie. A focused territory where you know the customers well is better than a large territory where you’re stretched thin. A broader region leads to more challenges. Why? You may agree to take on a new client without making certain they fit in your plan. 

What do you sell? What problems do you solve? Start there. If you don’t know this, you won’t know the types of companies/people you should have in your territory. Once you define your ICP, which specific companies have problems you can solve? Are your company’s customers in a particular industry or sector? Look for people similar to your existing customers. Then you can categorize companies and plan your approach. 

Great salespeople need to be creatively lazy

Steves’s answer probably isn’t one you’d commonly hear. Great salespeople are lazy. If you want a life outside of work you have to plan and strategize. You need the ability to strategize and learn quickly. You need to be creatively lazy. 

If you get inbound leads, you can't just jump on them. Look at your territory. If the company isn’t part of your ICP, don’t waste your time on them. Refer them to someone else that is a better fit for them. 

Steve worked with a lazy account manager who took long lunch breaks and went to football games during the workday. But he was a planner. He looked at opportunities, how to get them, and who he needed to talk to to get them. Once he had a strategy in place, he followed it. He didn’t have to work that hard because he strategized well. If you’re lazy, you don’t do things because you’re “supposed to.” You only do activities that help you reach your goals. 

What are you trying to achieve? What are your end goals? What’s the best way to achieve your goals? Do nothing that doesn’t fit in your plan. Avoid distractions. You can outsource those things. Ruthlessly focus on what gets you where you want to be. 

Focus on your niche in your geographical area

For one of Steve’s first sales jobs in Australia, he was told to cold-call people and sell his software to expand their clients. He called food distributors, manufacturers, etc. He learned his company’s software wasn’t suitable for them. They could modify it but didn't have the manpower to do so. 

So Steve went back to his manager and asked him to allow them to focus on who they served best. So the two salespeople doubled down on their niche and his company became the top-selling publishing software in the world. You need to have the right piece to the puzzle. Match what you have to offer to the people that need it in your geographical territory. 

Resources & People Mentioned

Connect with Steve Hall

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Jan 26, 2022

It’s not often that we have the honor of hosting a productivity and systems expert on the podcast, but on this episode we have just that. Liz Heiman is a national sales expert and the Founder and CEO of “Regarding Sales, LLC.” The firm she’s created focuses on building B2B sales operating systems that drive extraordinary growth. Liz and Paul continue the series on the topic of territorial sales planning by focusing on the nuts and bolts of what it takes to build a successful plan for your territorial sales efforts.

Outline of This Episode

  • [0:57] Why Liz believes territorial sales planning to be underrated in general
  • [1:38] The challenge of “reactive selling”
  • [2:35] Ingredients of the perfect territorial sales plan
  • [5:08] What makes for a great territorial salesperson
  • [6:03] Characteristics of a great territorial salesperson
  • [9:50] Liz’s top three territorial sales planning DOs and DON’Ts
  • [11:50] A territorial sales story (that happens over and over)

Why is territorial sales planning underestimated (and underutilized)?

It’s clear from a brief look across the sales landscape that the importance of territorial sales planning is not understood. Liz believes that it’s a huge mistake to think sellers can simply begin calling leads and make sales. A plan is needed to be most effective. But why don’t sellers and sales leaders build plans?

  1. They think that a number (sales goal) is a strategy, but it’s not
  2. They don’t know how to structure an effective plan, try it, and it doesn’t work. So they never do it again because it didn’t work
  3. Management pushes them to sell but doesn’t help them accomplish that goal

Reactive selling: an Achilles heel when it comes to territorial sales planning

Liz explains that one of the worst habits a salesperson can fall into is what she refers to as “reactive selling.” What is it? What is urgent, what comes across their desk or email each morning is what absorbs their attention. This sort of focus on what’s coming to them is misleading because what’s coming to them doesn’t necessarily get them where they want to go. To avoid reactive selling, a plan is in order. It’s vital to have an endpoint in mind and therefore be clear about the activities that will get them there. Planning is the only way to prioritize those specific activities, which is what makes the achievement of sales goals a reality.

What goes into the perfect territorial sales plan?

Before moving into the elements of a territorial sales plan, Liz reiterates a foundational principle: You must have a funnel/pipeline and understand what is in it. Understand your sales cycle and its velocity. Understand your qualifying process. Understand how many leads need to go into the top of the pipeline to generate the number of sales you need. Your pipeline is the main tool you use to execute your plan. When you understand it, you can create your plan by doing the following…

  1. Assess what you sold last year, who you sold to, how it happened
  2. Break up your territory into different segments (top clients, undersold clients, referral partners)
  3. Leverage existing relationships for referrals
  4. Uncover the sales activities that fill in the gaps and generate more qualified leads

A successful territorial salesperson looks like this…

A person who is successful at territorial sales is a person who can and does learn from their mistakes. Instead of beating themselves up over their missteps, they learn the lesson it has to teach them so that they never make that mistake again. It’s learning the skill of leveraging the mistake to serve you instead of holding you back. You use it to reach where you want to go.

Liz also points out that consistency is a multiplier. When you have a well-considered plan for your sales territory and implement it every day, regardless of what comes to you, success is going to come. The right behaviors done repeatedly build success.

This episode is full of actionable tips and powerful insights to help you build a territorial sales plan that will win. Listen to get all the details from Liz Heiman.

Resources & People Mentioned

Connect with Liz Heiman

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Jan 19, 2022

Sales superstars who work a territory — be that a geographic area or a particular industry segment — are hard to come by. But great salespeople with no experience in territorial sales can be trained, nurtured, and taught how to create an effective sales plan for their territory that leverages their natural ability into great growth and profitability. This episode features sales coach and trainer, Michael Griego who shares some of the characteristics of sales territory superstars, what goes into a great territorial sales planning process, and more.

Outline of This Episode

  • [0:19] Michael Griego:Sales leader, author, speaker
  • [1:02] Why territorial sales planning is overlooked so much
  • [1:50] The fundamental part territorial sales planning plays
  • [2:53] The ingredients of a perfect sales territory plan
  • [6:48] What are the attributes of a territorial salesperson?
  • [10:54] Michael’s tips for building your own territorial sales plan
  • [12:35] Michal's top 3 Sales Territory planning DOs and DON’Ts

Why is territorial sales planning so neglected?

Micheal is quick to agree that territory planning is often overlooked. He says the simple reason for that is that reps are too busy running deals, chasing situations, trying to get deals done, doing the admin side of things, etc. He explains that when there is no clear planning process that guides daily activity those other things take the stage and planning gets pushed to the side. A salesperson without a plan can even be very successful but not necessarily in a strategic or orchestrated manner.

That’s on an individual level, but Michael says the problem exists on an organizational level as well. Often, when he goes in to consult with a company they have some type of planning process in place but it’s many times a legacy process that needs to be revamped. It may also be a sloppy attempt at planning that needs to be tightened up. Michael insists that planning at a hierarchical level (from the territory level down to the daily activity level) is critical.

The components of an ideal territorial sales plan

The good news from Micheal’s perspective is that many things that need to be done to plan effectively are intuitive. Most sales professionals who begin a planning process start with assessment of the current state of the territory — which IS the place to start. Michael explains that a good structure is needed to put a stake in the ground and say “This is what the territory is and this is what I see, currently.“ Next, Michael suggests working out a “Top 10 opportunities” list and a “Top 10 prospects” list. Doing this forces sales reps to clarify what they are really dealing with and helps make the distinction between targeted prospects and active deals.

Beyond this is the need for a development plan. The question to be answered is “What are you doing to develop the pipeline?” Webinars? Mailing campaigns? Launches? Cold calling? Once implemented the development plan needs to be reviewed and updated on a 30-60-90 day basis. Listen to hear the rest of Michael’s recommended territorial sales planning process.

Attributes of a sales superstar that carry over into a territory planning mindset

In his book, “42 Rules to Increase Sales Effectiveness” Micheal outlines the attributes of sales superstars. He says these same 5 characteristics need to exist for those who excel in territorial sales. What are the 5 attributes?

  1. Be a driver (Be motivated, on top of things, eager to implement and take action)
  2. Be a technician (Become competent with your product/solution/industry through study)
  3. Be a facilitator (Learn to be an excellent communicator)
  4. Be an empathizer (Develop your people skills and learn to be relational)
  5. Be a servant (care for customers)

Michael’s insight into organizing a sales territory is so relevant and applicable you’ll want to listen to this episode a number of times. 

Resources & People Mentioned

Connect with Mike Griego

Connect With Paul Watts 


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Jan 12, 2022

To you, is territory sales planning as simple as, “I’ve got a territory, so my main goal is grow the client base within my territory”? If so, this episode’s guest, Paula White, says you could be missing the practical details that will enable you to do just that. Paula is a returning guest on this episode of Sales Reinvented and provides a significant bit of insight into how intentional and detailed planning, broken down into bite-sized pieces can help you grow sales volume within your territory.

Outline of This Episode

  • [0:19] Paula White: Champion of stand-alone digital sales channels
  • [0:43] The underrated activity of territory sales planning
  • [1:18] How planning fits into day to day activity and the benefits of doing so 
  • [3:28] Intentionality includes a “leave-behind”
  • [5:11] The power of a 30, 60, 90 day plan for every salesperson
  • [6:05] A summary of Paula’s quarterly plan, broken down into 30, 60, 90 day intervals
  • [6:55] Paula’s top 3 territorial planning DOs and DON’Ts
  • [9:22] Lesson-Learned: A favorite territory planning story from Paula 

Paula’s number one ingredient for sales territory planning: Quarterly snapshots

When Paula thinks about her sales territory, she doesn’t allow herself to view it as a huge, nebulous whole that has to be grown over the course of a fiscal year. She breaks it down into possibilities, by quarter. This enables her to work with manageable groupings of existing clients and potential clients without being overwhelmed… and she does this on a quarterly basis. 

When asked what that quarterly plan consists of, Paula says that in her approach she’s identifying who she’s going to target each month within the quarter. The rhythm that works for her is to focus on target customers or prospects during month one, what she calls “bottom customers” during month two (those who perhaps do a lower volume of business or have made minor purchases to date) and then her “middle customers” during month three. One of the things Paula likes about this approach is that it allows her to fit seasonal targets into her planning in a practical manner.

Great territory sales professionals are intentional

As you hear Paula speak about her approach to planning for her sales territory, one thing becomes evident: she’s intentional. She sets goals and integrates the steps she’ll have to take in order to reach those goals into her day to day planning. This plan guides her preparation for appointments and calls and even helps her stay on track during those calls. It also enables her to create what she refers to as a “leave-behind” for each appointment — a review of everything discussed during the call for the prospect or customer to review once the call is over. This kind of intentionality increases your confidence as a seller but more importantly, enables you to serve prospects and customers in a professional manner. 

30, 60, 90-day planning is essential for territorial sales

Paula integrates intentionality with her quarterly planning by breaking each quarter down into further blocks. She creates 30, 60, and 90 day plans for herself, much like a new salesperson may be required to do as they onboard with a sales organization. She says it’s a discipline that serves veteran sellers as well as newcomers. In these smaller plans, Paula writes down who she wants to meet with, what she hopes to accomplish, how she wants to get those things done, in detail, and more. At the end of these 30, 60, 90 day blocks, she evaluates by asking a number of questions...

  • How did she do at hitting her goals?
  • What prevented success?
  • What didn’t go according to plan?
  • How can she optimize her opportunities during the next 30 days?

Paula’s top 3 dos and don’ts for territorial sales planning

To sum up Paula’s perspective on planning for success in territorial sales, she offers three “DOs” and three “DON’Ts”:


  • Be intentional and specific
  • Create a 30, 60, 90 day plan
  • Keep a smile on your face (positivity empowers your planning and production)


  • Waste your time by creating a plan but not following it
  • Assume everything will be fantastic. You have to course-correct as you go
  • Get down on yourself. Sales is tough and requires perseverance and confidence

Connect with Paula White

Connect With Paul Watts 


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Jan 5, 2022

If you are a sales leader, how do you go about planning your organization’s sales territory approach? Whether you’re dealing with geographic territories or industry niches and companies within those niches, you need to use every resource available within your team to establish your territories wisely. Brynne Tillman has a wealth of insight into this sort of planning and specializes in using LinkedIn to find the best territorial fit between the target territory and the sales professionals on your team. Listen to this episode to get all the details from Brynne’s experience.

Outline of This Episode

  • [0:18] Brynne Tillman: The LinkedIn Whisperer
  • [1:16] Territories help with organization and sales networking
  • [3:44] Brynne’s ingredients for the perfect sales plan
  • [5:36] A bonus for those establishing sales territories
  • [6:33] What makes a great territorial salesperson?
  • [9:43] Brynne’s DO’s and DON’Ts for sales territory planning
  • [13:57] A favorite territory sales planning story from Brynne (and the lesson learned)

Territorial sales planning can make a bottom-line difference

Strategically approaching your sales territory planning will yield tremendous results if you take the time to do it. And those in leadership within sales organizations especially need to learn how to establish and assign territories for maximum impact. Brynne says that when doing so, every element that goes into creating a lead list should be very focused. When you can define not just what to do but with whom to do it, you can be much more productive and focused. This is where Brynne’s expertise with LinkedIn shines.

She suggests that sales professionals search their ideal buyers (titles, positions, companies) and their geography using LinkedIn. Even the free version can perform searches like this on a granular level. You’ll be able to build a sizeable list of leads to qualify and approach using the advanced search functionality offered on the platform. When you do this, you don’t waste time cold-calling people who aren’t a good fit for your offering. That results in more targeted conversations, which will impact bottom-line sales. 

What is the most effective way to sell what you sell?

Many sales leaders grab a map and set of pins to begin their sales territory planning, but Brynne says that’s one of the least effective ways of going about it. She suggests that you examine your existing book of business to first, understand who your target market is and what they typically buy from you. Using that data, look at the territory in question and find the companies and organizations that possess what you might call a “look-alike” profile. In the end, you want to ensure that the filters you’re using to create your territorial sales plan produces a list of prospects that are achievable for the sales rep, both in terms of profile and geography. Brynne calls this “the planning before the planning” and says it’s a huge step toward empowering sales reps for success.

The ingredients of an effective territorial sales plan

Too often, sales leaders don’t consider their sales team’s existing relationships when assigning territories. Brynne says this is a huge mistake. As a sales leader, you can do your own research to ensure you are assigning the right sales rep to the right industry niche or geographic territory using Linked In. First, ensure you have connected with the sales rep yourself. Next, use LinkedIn’s search functionality to research your sales rep’s connections by industry and geography. You may find that a rep you intended to assign to a specific city has very few existing relationships there while another on your team has many. A successful sales rep rises and falls on relationships so don’t leave out existing connections when devising your territory strategy.

Brynne’s DOs and DON’Ts for territorial sales planning


  • Ensure that your LinkedIn profile clearly speaks to your target buyers
  • Sales leaders: Search your rep’s contacts to ensure they fit the territory
  • Talk to your reps to ensure they fit the territory you’re assigning them to


  • Don’t use a map and pins to assign territories
  • Take an account-centric approach, not just account-based
  • Allow for flexibility when assigning territories because of relationship opportunities

Resources & People Mentioned

Connect with Brynne Tillman

Connect With Paul Watts 


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Dec 29, 2021

When salespeople were forced to switch from face-to-face selling to virtual selling, they were forced to learn a different medium of communication. What you used to be able to communicate with your face, body language, energy, etc. has to be squeezed into a small square on a computer screen. Your customer doesn’t have the context of face-to-face. It requires learning new skills. In this episode of Sales Reinvented, Julie Hansen shares how acting skills can benefit a salesperson and help them succeed in this virtual reality we now live in. 

Outline of This Episode

  • [0:43] The difference between selling face-to-face and selling virtually
  • [2:38] How businesses can improve virtual selling
  • [4:47] Julie’s virtual selling blueprint
  • [6:54] Attributes + characteristics that make a great virtual seller
  • [9:34] Tools, techniques, and strategies to improve virtual sales 
  • [11:55] Julie’s virtual selling dos and virtual selling don’ts
  • [16:07] Get the virtual training you need to succeed in your role

The difference between selling face-to-face and selling virtually

Julie has a background in acting. Most actors/actresses start their careers doing live theatre. You can see your audience and what lands—or doesn’t—and adjust accordingly. Virtual selling is similar to moving to on-camera work. 

When Julie moved from live audiences to camera, she did what she did for theatre. But the director pointed out she wasn’t looking in the right place, she was out of frame, and was distracting. She learned she had to get new training to communicate in the new medium. Salespeople need to acknowledge that and learn new skills so they can communicate in a virtual environment. 

How businesses can improve virtual selling

Organizations learned that they can be more cost-effective doing sales calls virtually. Plus, McKinsey found in their research that more than three-quarters of B2B buyers prefer remote interaction versus face-to-face. You need to adapt to the new reality.

Most organizations throw tools and technology at their salesforce but haven’t realized that communication differences need to be addressed. How does the camera read behavior? What about your eye contact and facial expressions? Are you communicating what you need to? 

You have to learn to connect one-on-one on camera because sales are all about building relationships. People buy from people they like and they feel confident with. So you have to learn to establish those relationships through a camera. That’s where the growth needs to be. If you can do that, you’ll rise to the top and stand out. 

Attributes + characteristics that make a great virtual seller

Julie believes that the qualities needed to succeed are the same, whether in person or virtually. You need to be credible, keep your word, be authentic, show empathy, be an active listener, etc. But those qualities are often lost in a virtual exchange, so you have to adjust the way you communicate them.

In a face-to-face conversation, if someone stared at your shoes the whole time, you’d feel like they weren’t interested. But it happens on video all the time. You may be looking at the customer’s image, screen, tools, etc. You need to understand that the quality of active listening requires you to behave differently. You have to know when to look at the camera directly. Your fave must communicate the emotions you think it is.

What tools, techniques, and strategies does Julie recommend to improve how you portray yourself on video? Listen to learn more! 

Julie’s virtual selling dos and virtual selling don’ts

Julie shared some amazing tips to help you improve your skills:

  • You have to record yourself and you have to review it so you know how your customer sees you.
  • You have to bring more energy to a virtual call because the camera takes some away. You can be natural and comfortable but you can’t come across as laid back and low energy. Get yourself in a good high-energy state before jumping into a conversation.
  • Make sure that you are managing your tools and technology and engaging your customer. Salespeople tend to go into monologues because customers aren’t responding. Recognize that people are more passive on video and engage far less. You have to work harder to foster engagement. 
  • Don’t stare at your customers' image when they’re talking—look at the camera. But if you’re looking at the camera, how do you read body language? There are different techniques, one of which is using peripheral vision to glance at their image. 
  • Don’t assume that your customer will answer you right away. Give them a second to respond. If you ask and answer your own questions, you’ve trained them that they don’t have to respond. Silence is uncomfortable, but you have to allow them time to process and answer. 

Get the virtual training you need to succeed 

Julie got a call from an experienced enterprise sales rep who was a top biller before things moved virtually. He felt like he wasn’t connecting with his customers and that he had lost his superpower. When Julie worked with him on camera, it was obvious his personality wasn't coming across. He felt scripted and his discomfort was obvious.

She worked with him on improving his eye contact, body language, energy, and what his face was portraying. After working together, he went back to a customer where he had been shut out of a big deal. He put together a compelling and engaging personalized video that got him back in the running. 

You have to admit that you don’t know what you don’t know and get the help you need to adapt to this new environment. Don’t sit and suffer in silence. Stand up for yourself and get the training that you need to succeed. 

Resources & People Mentioned

Connect with Julie Hansen

Connect With Paul Watts 


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Dec 22, 2021

According to Walker McKay, a salesperson’s actions, attitude, and approach can lead to digital improvements. What should those actions look like? What characteristics do you need to embrace? What approaches are successful? Walker McKay answers these questions—and more—in this episode of Sales Reinvented. 

Outline of This Episode

  • [0:53] The difference between digital and social selling
  • [2:07] Improve digital selling with your actions, attitude, and approach
  • [3:37] Walker’s ideal digital selling blueprint
  • [5:26] The attributes or characteristics of a great digital seller
  • [7:27] Tools, techniques, or strategies to improve digital sales
  • [8:42] Top 3 digital selling dos and top 3 digital selling don’ts
  • [11:04] Digital selling opens up a whole new world

Actions, attitude, and approach = digital improvement

Digital selling is important because it’s nearly impossible to get face-to-face with people anymore. People are working from home and you can’t just show up at their “office.” So you have to find other ways to connect with people and hold conversations. Organizations need to create expected behaviors around digital selling regarding:

  1. The actions you take
  2. The attitude you have
  3. The approach that you take

You have to start with the actions. What is the expected behavior? How many LinkedIn posts should somebody do? How many times should you reach out per week? Companies need to get comfortable that this is the way things are being done. So it’s time to build behaviors around getting appointments via text, phone, social media, and video. 

Walker’s ideal digital selling blueprint

Where should you go to find business? If it’s on LinkedIn, you can download your connections onto a spreadsheet. You can match it with your client list and make sure you’re connected with people you’re already doing business with. 

Secondly, Walker would take that list and look for some low-hanging fruit you hadn’t talked to yet. How will you get in touch with them? You can send LinkedIn messages, DMs, text messages, phone calls, and emails. You need to touch people 6–7 times using different channels to get their attention. The goal is to set an appointment, right? Set a meeting over Zoom or a similar channel. 

The attributes or characteristics of a great digital seller

Old school B2B salespeople might be in their 40s, 50s, or 60s. Even so, an openness to technology is key to their success. Secondly, salespeople need to have a strong why behind their success. You have goals you want to accomplish and achieve in life. Are you disciplined enough to reach out to people, send messages, and keep track of it? It is discipline and a desire to win being put into place.

Are you posting things on different channels? Walker has found posting a video or a how-to on social channels to be effective. If you’re selling insurance, you might post “5 Ways to Make Sure You Get the Right Insurance.” You have to be able to write well and teach people with your posts. If you’re seen as a teacher, people will come to you for help and you’ll become the professional in your space.

Digital selling opens up a whole new world

Walker is always looking for sales experts to be guests on his podcast. He was using LinkedIn to reach out to people but wasn’t getting a great response. He was reaching out to 5 people a day. But he connected with someone named Casey Jones. She didn’t respond. 3 days later, he messaged her again and they started a conversation. Turns out, they had a great connection. She was one of his best podcast guests and they’ve since collaborated on three different business deals. 

There is a network outside of you through the digital world that is much bigger and better than what you could have face-to-face. Work to build your network and ask for what you want. There’s a tremendous world of business out there. 

Connect with Walker McKay

Connect With Paul Watts 


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Dec 15, 2021

A digital sales strategy can include social selling, video communication, and great content as a mechanism to communicate with a prospect. Whether selling digitally or in person, Liz Heiman believes that every successful seller models the 4Cs of selling. What are these characteristics? Listen to this episode of Sales Reinvented to learn more! 

Outline of This Episode

  • [0:43] The difference between digital and social selling 
  • [1:55] How to improve your digital sales
  • [3:42] Liz’s digital selling blueprint
  • [5:46] The attributes/characteristics
  • [7:22] Tools, techniques, and strategies to improve 
  • [8:33] Top 3 digital selling dos and don’ts
  • [10:13] Be creative, curious, and compassionate

How to improve your digital sales

Liz emphasizes that good selling is good selling whether it’s digital or in-person. You can’t get away with bad habits anymore because digital noise has become so loud. Just “checking in” isn’t effective. You need to be heard through the noise. If you’re going to be a good seller, you need to understand who you’re selling to and what matters to them. Then you need to have a valid business reason for interacting with them. Be relevant and intentional with your selling in the digital world. That starts with putting in place better basic selling skills. 

Liz’s digital selling blueprint

Most of Liz’s clients deal with complex B2B sales (with multiple people involved). So her digital strategy starts with an account-based approach. She works with sales and marketing to reach out to the people who influence buying decisions within a company. It takes a targeted approach with clear messaging and predefined actions that each team takes. 

Secondly, Liz recommends checking in on buyers with intention. She has her sales team—the moment they finish the last action—identify what the next action and message will be. That goes into their CRM so when they make the next interaction they remember what they’re supposed to do. 

If you have a CRM, take careful notes and list your next action. Use the tool to help you be effective. When Liz makes a call to a prospect, she looks at their last conversation. Secondly, Liz believes sending a video is imperative. If you can’t pop your head in, sending a quick video is a great way to do it. 

Liz’s Four Cs of selling

Liz believes it’s the same skills that any seller should have: the “Four Cs of selling.” You need to care about and be compassionate for your customers. You also need to be creative and curious. These skills will help you be effective. If you’re curious, you’ll do research, take notes, and look for pain points. You’ll hear what your customers are telling you and acknowledge and engage with what they’re dealing with. 

If you can’t get their attention with one strategy, you’ll get creative and try another. If your solution doesn’t work, how can you find one that does? Those are the things that matter, digital or not. You have to work harder to develop the human connection. 

What tools, techniques, and strategies can you use to improve your communication? What are Liz’s top 3 digital selling dos and don’ts? Listen to learn more!

The 4 C’s of communication in action

Liz tells people to use video but she hates video. But a year and a half ago, she decided to send her follow-up notes as a video. She had a client that hadn’t been responding, so she sent a video. One of the prospects had been in the process of firing someone. She asked if he was able to make a decision. 

He wrote back and said, “You must have the most amazing CRM that you can remember what we talked about last time.” She cared enough to remember what they talked about and reach out to see if they needed her help. When you care about people and listen to them, it works. Reach out to customers in a way that’s easy, convenient, and helpful for them. 

Resources & People Mentioned

Connect with Liz Heiman

Connect With Paul Watts 


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Dec 8, 2021

Salespeople are still struggling to adapt to all of the changes that the Covid pandemic has brought about. Virtual selling is still largely at play, with some in-person interaction still sprinkled in. Tom Pisello believes that to adapt, you need to become laser-focused on helping prospects become aware of and solve their problems. To do that, you have to identify your own struggles to become more effective. Tom shares insight into this process in this episode of @SalesReinvented! 

Outline of This Episode

  • [0:49] The difference between digital and social selling
  • [3:21] How to succeed with virtual selling
  • [9:32] Tom’s virtual selling strategies 
  • [10:59] Attributes and characteristics of a great seller
  • [12:04] Tools, techniques, or strategies to improve virtual sales
  • [14:15] Top 3 virtual selling dos and don’ts
  • [15:17] Foster engagement in virtual sales presentations

How to succeed with virtual selling: identify your gaps

Sellers are frustrated with how much longer purchasing decisions are taking and how many people are involved in the process. It can be difficult for them to manage. But Tom emphasizes that if you look for what buyers are saying their challenges are, it can be a turning point. When the Rain Group surveyed buyers on what they thought of sellers in the digital environment, four gaps that were recognized:

  1. Leading a prospect through a thorough discovery: Don’t just show up and throw up and make discovery as part of the process. Give a presentation with an interactive demo. 
  2. Mapping solutions to the problems that were identified: Do your best to address the root cause problems that the buyer is facing. 
  3. Listening skills: Many sellers don’t stop talking. There’s a loss of eye contact, talking over the other person, etc. You have to slow your roll in virtual meetings. Don’t be afraid to stop early and leave a cliffhanger and time to talk next steps.
  4. Making the ROI clear to the buyer: Tom’s nickname is “The ROI Guy.” Buyers care about the problem they’re solving and the business outcomes you can assure they get. Focus on the outcome you’ll give them—not what you’re selling. What can your product solve? What can it deliver in terms of quantifiable business value? Make it clear

How to succeed as a virtual seller

How do you present your sellers with discovery guides and interactive presentations? Can you provide your sellers with an interactive diagnostic assessment or a problem/solution guide to use with customers? You have to provide an interactive value assessment tool so sellers can collect data from the customer and do the number crunching to make a business case. 

Make sure you’re implementing conversational intelligence tools so you don’t have to have your head down to take notes. You need a good video presence and the ability to listen more than they talk. So learn how to maintain eye contact on video calls. 

When you do talk, you need to ask good in-depth discovery questions that help buyers be introspective. A good seller is armed with good content and tools. They’re leveraging dynamic presentations and assessment tools to add value, insight, and guidance. 

Tools, techniques, and strategies to improve virtual sales

Tom recommends that content enablement groups work to examine PDFs, videos, guides, etc, that are being provided to their salespeople and think about retooling them. Can you make them interactive? Can you click on elements? Customers don’t have the patience to sit through a deck. You have to be able to pivot the conversation to what the customer wants to talk about and have content to support it. 

Tom loves doing diagnostic assessments to assess a company’s maturity and where they are in the journey. You can map out improvements that they’d like to make and give intelligent recommendations. You can benchmark them against peers. 

What about business value assessments? What challenges are they facing? What is it costing them? What’s the value potential of implementing a solution? What evidence can you share that you can deliver on this? The right tools can make a difference. 

What are Tom’s virtual selling dos and don’ts? Listen to learn more!

Foster engagement in virtual sales presentations

Tom once had 16 people in a company’s buying committee in a virtual meeting. With a crowd that large, you want to be mindful of who is paying attention. What does everyone care about? The customer was early in their decision-making process. So instead of talking about the solution, Tom mapped a day in the life of their customer’s customer and how they helped to overcome their problems. They went into how they could help address the friction this prospect was dealing with in their selling process. 

As they walked through the pieces of their sales process with the customer, he got almost everyone on the call to participate. Tom made sure he got input from everyone to make sure everyone was engaged. They took notes on what was important. When they went into the solutions part of the call, they tied back to specific people and pain points. 

Tom notes that people can be afraid to speak up in front of their CEO and other executives, so you have to be conscious of the political dynamics within the environment. You can overcome that by calling on specific people to contribute to the conversation and be heard. Above all, spend time walking through discovery with the group and make sure everyone is engaged in the pain-point portion. Be aware of the dynamics that occur and be ready with strategies to engage everyone. 

Resources & People Mentioned

Connect with Tom Pisello

Connect With Paul Watts 


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Dec 1, 2021

Digital selling encompasses a variety of different communication channels. Whether it’s via social media, texting, email, or video, a great digital seller has to be agile and willing to use whatever medium their prospects and customers prefer. Why is that so important? Lori Richardson shares her thoughts in this episode of Sales Reinvented! 

Outline of This Episode

  • [0:40] The difference between digital and social selling
  • [1:56] How to improve digital selling
  • [2:40] Lori’s digital selling mindset
  • [3:46] Attributes of a great digital seller
  • [5:01] Tools, techniques, and strategies 
  • [6:35] Top 3 digital selling dos and don’ts
  • [9:42] Communicate how your prospect prefers

Attributes of a great digital seller

You have to be able to prospect digitally. You need to do value proposition work. You need to be able to connect well with people. Then you need to build your communication skills and tools to have ongoing conversations to build trust with your buyer. You must help them with services you offer—or don’t. You want to help them in any way you can, even if it means referring a prospect to someone else. 

Lori believes there are some key sales competencies that aren’t based on personality that must be mastered. These traits help people sell more:

  • A desire and commitment to sell: Do you take responsibility? Do you have a good outlook? How motivated are you?
  • Consultative selling skills, selling value, and learning to avoid discounting.
  • Are you coachable and trainable? 

These things are critical to successful selling.

Tools, techniques, and strategies to improve digital sales

Do you have a solid methodology and process in place? Are you engaging in tasks that lead to closing sales opportunities? There are thousands of tools available for marketing and sales success. Lori emphasizes you must master social selling and video, know how to follow prospects and clients on social media, and learn how to use fundamental tools like Sales Navigator. 

Lori’s top tips for digital selling

What are Lori’s digital selling tips?

  • Be genuine and authentic—it’s more important now than ever.
  • Build your brand and gain visibility on different platforms.
  • Be consistent and follow-up with prospects with a clear process in place.
  • Don’t do the spray and pray on social media. When you meet someone at an event, you don’t sell to them immediately. Why do it with digital interaction?
  • You’re in it for the long haul. You don’t have to get a deal today, so don’t push yourself on people. Sell products and services that you trust and believe in that add value for your buyers. 
  • Always add value in every interaction with a prospect or current customer. If you do this every time, people will want to talk with you. 

Communicate how your prospect prefers

Lori helped a company that had found her virtually and reached out through texting. By returning their texts, Lori answered enough questions that they felt comfortable having a phone conversation. The phone conversation led to Lori offering them some services. That turned into a solid six-figure deal. It all started with texting. They turned out to be a great client that Lori still works with today.

If someone emails or calls, Lori responds immediately. If you get back to people quicker, you have the highest chance of closing business. Even if you just schedule a time to talk further, people are blown away. Likewise, if texting is your client's preferred mode of communication, by all means, text them. 

Resources & People Mentioned

Connect with Lori Richardson

Connect With Paul Watts 


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Nov 24, 2021

Gartner’s research has shown that buyers complete 57–80% of their buying journey digitally well before they even talk to a salesperson. That’s why—according to Subhanjan Sarkar—you have to find a way to engage with your buyers before they become a lead. How do you accomplish that? Subhanjan shares some thoughts in this episode of Sales Reinvented! 

Outline of This Episode

  • [0:55] The difference between digital and social selling
  • [2:35] How can you influence the customer in their buyer journey?
  • [4:51] Subhanjan’s ideal digital selling strategy
  • [7:04] 5 attributes of a great digital seller
  • [8:29] Tools + techniques + strategies to improve
  • [11:33] Top 3 digital selling dos and digital selling don’ts
  • [13:48] A genuine interest in the customer’s benefit is key

How can you influence the customer in their buyer journey?

Gartner’s research shows that about 17% of a buyer’s journey is spent between multiple vendors. You may only have 2–3% of their entire journey dedicated to you. So you need to find a way into the 57–80% of the journey that the buyer experiences independently. That’s why digital selling is critical. 

You must build your position as a thought leader to do that. Buyers don’t want to buy from vendors who only compete on price. Pricing cannot be a tool that everyone uses. To differentiate yourself, you have to understand your buyer. You can learn what a buyer is doing long before you meet them. 

Subhanjan’s ideal digital selling strategy

Subhanjan recommends mapping a buyer’s universe and start interacting early using technology and adding in a physical meeting when necessary. He recommends that you start gathering and learning about your industry verticals and create a thought leadership position in the industry. 

If you aren’t a good fit for a client, send them toward a competitor—don’t create a dissatisfied customer. If you direct them to a better fit they’ll remember you and become a fan because you cared more about solving their problem than getting a sale. Next time they have a problem, they’ll come to you first. 

What are the five attributes of a great digital seller? Listen to hear Subhanjan’s thoughts!

Tools + techniques + strategies to improve digital sales

Subhanjan believes that one of the most critical strategies a salesperson needs to embrace is early engagement. You can’t just start with a lead. By the time you get a lead, 80% of their journey is over, right? But what if you've already engaged with this lead somewhere online because you’re a thought leader in the industry? 

He also emphasizes that you need to be able to start a conversation and continue it without friction. You can share information and bounce ideas off of each other. That will prove extremely valuable. 

Lastly, you must master the specific tech tools that your company uses. He points out that everyone uses spreadsheets yet everyone is awful at them, even after 40 years. Salesforce, Hubspot, etc. are complex things you have to invest time in to master. Do this with whatever tools are necessary for your trade. 

A genuine interest in the customer’s benefit is key

A very large company in India wanted to build a vendor relationship management system (VRM). They had multiple vendors engaged. One particular vendor started the conversation by saying, “You don’t have to buy from me—have you thought of applying design thinking to the process?” The company didn’t know what design thinking was, so he offered to run a design thinking workshop for the leadership team. 

He put on a one-day virtual workshop with an expert from MIT. They learned about digital thinking and applied it to the software they were creating for managing vendors. At the end of the day, the buyers got a better spec sheet for their VRM. They came back and took consultative input from this rep and ended up buying from him. The other vendors had no clue what was going on. This is living proof that a genuine interest in the customer’s benefit is key. 

Resources & People Mentioned

Connect with Subhanjan Sarkar

Connect With Paul Watts 


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Nov 17, 2021

Kendra believes the way we sell has changed forever. Now, we have a whole new way we can work with people that we can layer onto traditional selling. You don’t have to get on a plane or drive to meet a prospective customer—you can still connect with people digitally. Digital selling allows you to meet with more people and connect with them in bite-size pieces. 

Plus, if you’re going to be successful with selling, you need to try new things. Kendra points out that you should have been selling digitally before the pandemic hit. The pandemic should have just accelerated your current strategy. 

Outline of This Episode

  • [1:03] The difference between digital and social selling
  • [1:41] How to improve digital selling capabilities
  • [3:11] The perfect digital selling strategy
  • [5:02] Attributes and characteristics of a great digital seller
  • [6:33] Continued communication is key
  • [8:05] Kendra’s top 3 digital selling dos and don'ts
  • [11:13] Be on the leading edge of technology

Attributes and characteristics of a great digital seller

They can be trained on a CRM, how to use LinkedIn, etc. but people most often get tripped up on video. Why? Because you are front and center. You can’t look down and take notes and it’s difficult to look someone in the eyes. Salespeople have to master connecting and engaging through video.

Kendra also emphasizes that writing has never been a more critical skill than it is now. You have to be able to write emails, text messages, and social media posts. Emotional intelligence is also critical. Can you sense another person’s feelings when you’re limited with body language? 

Continued communication is key

Kendra believes that continued communication is important from a strategy perspective. Whether it’s recapping a conversation via email, video, or text—you need to stay in touch frequently. In the past, salespeople didn’t always do this and could get away with it. But things are more competitive now than ever before. If you’re going to differentiate yourself, frequent communication via a variety of tools is important. 

Kendra’s top 3 digital selling dos and don'ts

Kendra’s digital selling dos and don’ts are stellar: 

  • Don’t shy away from using your camera, even if your client doesn’t turn there’s on.
  • Communicate more frequently using different mediums—including text messages. 
  • Pay close attention to what your prospects and clients are saying so you can tailor your discussion. 
  • Don’t use the same canned email for every sales situation. Sequences can help you streamline the process but the sequence needs to be tailored so your prospects and clients feel heard.
  • Don’t use the same communication method. Kendra had a prospect that wouldn’t respond to email or voicemail. So she sent a LinkedIn message to mix it up. If you have their cell phone number—and they use it in their email signature—it’s perfectly acceptable to send them a text. 
  • Don’t shy away from using the phone. It was the “first” digital strategy. 

Be on the leading edge of technology

When Kendra first started in sales, she had too many clients to cover on her own. Kendra had 300 installed accounts. She didn’t have time for everything she had to do and still hit her quota. She couldn’t go out and meet with every single client and collect orders, which felt like the most important part of the process. You need that face-to-face interaction and connection. 

But why couldn’t she get some of the information from a fax (which at the time was new technology)? She’d simply start to accept orders from clients via fax. Ever since, she consistently looks at her process and asks, “What can I do that’s different from everyone else? How can I be the leading edge and stand out?” 

Kendra got an award for taking orders over a fax machine because no one had done it before. All because she took initiative and focused on being on the leading edge of technology. 

Connect with Kendra Lee

Connect With Paul Watts 


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Nov 10, 2021

Darryl admits that digital selling is hard because there’s a lot of noise out there. The sales industry has a propensity toward reusing what’s been done before—the same emails, same LinkedIn sequences, the same ad layout, etc. and it becomes noise. So what do you need to do to improve? Hear Darryl’s thoughts in this episode of Sales Reinvented!

Outline of This Episode

  • [0:53] The difference between social selling and digital selling
  • [2:41] Understand your customer profile
  • [5:15] Darryl’s evolving digital selling strategy
  • [8:50] The attributes/characteristics of a great digital seller
  • [12:07] Tools, techniques, and strategies to improve digital selling
  • [16:17] Top 3 digital selling dos and digital selling and don’ts
  • [19:19] Build thought leadership on social media

Understand your ideal customer profile and personas

Who are you targeting? It can’t just be “anyone in high tech.” You have to be granular. Having 10+ granular customer profiles is fine. Then you develop your personas within those profiles. Darryl is the CRO of VanillaSoft and they target people who are the head of sales, head of marketing, head of operations, head of finance, and the head of IT. If you don’t know their world, you can’t create hyper-personalized messaging or content that resonates with them. Salespeople drop the ball by being too generic. You need to be specific to catch more fish.

Darryl’s evolving digital selling strategy

Darryl’s digital strategy starts with account-based marketing and selling. You identify your ICPs and personas and build lists. This can give you 50 unique lists with a specific message. Then you need to advertise where they live (Google, LinkedIn, industry forums, etc.). When they come to your website, you want to be able to track their IP to see where they’re coming from. You present content on the website related to that persona. It’s about building a collection of signals. 

Then, you put programs in place to nurture and grow the leads. It takes 9–12 touches before someone responds. So you want to use a combination of social, email, SMS, and even a phone call to get them to engage. Make sure you have a sales enablement platform in place so you can see when they’ve opened the content, if they’ve shared it, if they’ve watched a video. All of these things are signals that help you have a hyper-personalized engagement attempt to get someone to a conversation. 

The attributes/characteristics of a great digital seller

A great salesperson logs into their CRM and looks for signs of engagement or conversion. If there is a signal, they use their digital tools to identify their top targets and get them in cadences to engage with them. 

Secondly, they must schedule time to go to forums, discussion groups, or wherever conversations are taking place and engage without pitching. It’s about establishing your own brand and thought leadership. Darryl emphasizes that you must also plan engagement so that everything is hyper-personalized to a prospect’s personas and signals. 

You can’t send people a generic template email or social touch. You can’t look for shortcuts and means to spam people because it’s a “numbers game.” If you aren’t converting, it doesn’t matter what your numbers are. People buy from people and if you don’t make it relational and relevant to them, they won’t trust you or find you credible. The buyer will walk away. You’ll have spent a boatload of money with no ROI because you tried to scale and take shortcuts.

Engage in your community and contribute to conversations without the expectation of receiving anything in return. It’s a long game to build your reputation and street cred. But Darryl emphasizes that it’s amazing the volume of deals that come to you when people like and trust you. It’s the lowest acquisition cost and highest conversion rate. 

Build thought leadership on social media

When Darryl started at VanillaSoft in 2017 he had zero social media presence. LinkedIn was simply a vehicle for his resume. He recognized that he didn’t have a lot of budget, so he couldn’t compete on a digital spend strategy. So he took the route of LinkedIn. He saw traction within 6 months when he had a crowd around a trade show booth. 

One year later, after continuously sharing content on LinkedIn, that same trade show booth was packed. People knew his name. This was happening around the world. Everyone came to the booth looking for him. That’s when he learned branded content and contribution to conversations was a powerful driver. 

VanillaSoft got a ton of business they wouldn’t have gotten otherwise. Nothing else had changed at the company. The only change was a personal brand presence geared toward building a network.

Resources & People Mentioned

Connect with Darryl Praill

Connect With Paul Watts 


Audio Production and Show notes by

Nov 3, 2021

Digital sales are about leveraging yourself, your service, your products, and the available digital platforms to build relationships. Social selling is where you get to socialize, connect, and have conversations. Liz Wendling emphasizes that social channels are connected to real people in the real world having real conversations. You have to humanize the connection so they feel you’re there to help. One of the ways Liz connects with potential clients is through her “Verbal 2x4.” Listen to this episode of Sales Reinvented to learn more about her social selling strategy!

Outline of This Episode

  • [1:21] The difference between digital and social selling
  • [2:27] How to improve your social selling skills
  • [3:36] How to use Liz’s “verbal 2x4”
  • [4:48] The characteristics of a great digital seller
  • [5:55] Stop apologizing and stop being self-serving
  • [7:41] Top three digital selling dos and don’ts
  • [10:11] Liz’s verbal 2X4 put into practice

How to improve your social selling skills

Liz sees room for improvement in both empathy and understanding as well as flexibility and advocacy. Selling isn’t about pushing your products but listening to your potential customers to understand what they need. Only then can you solve their problems. You also have to be flexible with the changing marketplace. Potential clients want to work hand-in-hand with someone who wants to help and believes they can do so. 

Liz’s strategy is perfect because it works for her. She makes sure her message hits someone with a “verbal 2x4.” She wants to get their attention to move them toward a conversation. What can you do to get someone’s attention? What can you do that lands with an impact?

The characteristics of a great social seller

Authenticity, flexibility, and dedication are necessary attributes for any seller. Liz emphasizes you must be flexible in your process, authentic in your approach, and dedicated to follow-up and follow-through. You have to be able to have conversations (and resurrect the dead ones). Many people give up on themselves far too early in the process and blame it on the customer because “they don’t know what they want.” Be flexible and shift the message or conversation to re-engage potential clients. 

Stop apologizing, stop being self-serving, and start serving

Liz implores salespeople to stop apologizing and being self-serving with messages. What does that mean? Liz gets far too many messages saying, “I’m so sorry to bother you…” or “I know you’re busy, so I’ll be brief.” It not only puts the salesperson in the less-than position but does nothing to build confidence in the person you’re reaching out to. Get rid of apology language.

Secondly, don’t make it all about you. Make it all about your customer. Don’t say things like, “I’d love to get on your calendar” or “I’d love 30 minutes of your time.” You’re telling someone what YOU want instead of inviting them into a conversation that they want to be a part of. 

What are Liz’s top three digital selling dos and don’ts? Listen to learn more!

Liz’s verbal 2X4 put into practice

Liz teaches her clients to prospect on LinkedIn with a “verbal 2x4.” Liz focuses on the pain, problem, challenge, issue, or dilemma that her target market is muddling through. One area she focuses on with her consulting practice is family law attorneys. They’re spending a fortune to get leads. But they often fall short in sales conversations and conversions—so they’re losing a lot of money. 

Liz’s message hits home: “Many of the firms I work with are struggling with this, they’re spending a fortune on that, but here’s what the end result is.” Then she’ll ask for a conversation. They often respond with, “Are you a fly on the wall? How do you know this?” 

They think their attorneys are bad at closing, not fully realizing that they’re actually bad at opening. Instead of her pushing for a conversation, they’re the ones asking to get on her calendar. The outcome is always a great conversation. If you have a message that lessens the noise, you can have real honest conversations from an authentic place. 

Connect with Liz Wendling

Connect With Paul Watts 


Audio Production and Show notes by

Oct 27, 2021

According to Fred Copestake, social selling is using the platforms and technology available to you to create a personal brand and start conversations. Digital selling is using technology to continue conversations. The use of video (synchronous or asynchronous) is a piece of the puzzle that’s often neglected. Hear why Fred thinks that’s a huge mistake in this episode of Sales Reinvented!

Outline of This Episode

  • [1:08] The difference between digital and social sales
  • [1:49] How to improve digital and social selling
  • [2:36] Fred’s perfect digital selling strategy
  • [3:50] The attributes of a great digital seller
  • [4:51] Tools, techniques, and strategies to improve
  • [7:55] Top three digital selling dos and don’ts
  • [9:58] What not to do when recording a video

Fred’s perfect digital selling strategy

Fred’s digital selling blueprint is built around video. What do you need to do on video? What’s the purpose? To communicate or achieve a goal, right? Salespeople need to be equipped with the time and skills to utilize video with their prospects and customers. The use of video in digital sales is what will keep them engaged and move the sales process forward. 

Tools, techniques, and strategies to improve

Fred recommends Vidyard all the time as an asynchronous video option. It’s free and easy to use. If you’re talking synchronous video, you’ll need Zoom, Teams, etc. Then you need to figure out where and how to apply it. Where can it be used in the process? With prospecting? After-meeting follow-ups? To send a proposal? 

What is the video trying to achieve? Fred emphasizes that you must be succinct and punchy. You can get a lot across if your video is well-constructed. Another expert tip? Fred recommends investing in a great microphone to make sure you’re recording great audio. If people can’t hear you, they check out and lose concentration. The perceived credibility of the speaker also lowers if they can’t hear you. 

Top three digital selling dos and don’ts

Fred shares some great dos and don’ts: 

  • Get a good microphone.
  • Don’t mess about with childish backgrounds in your videos.
  • Use a natural background that is tidy.
  • Avoid moving off-screen or out of the shot. You are on the video all the time—act like it. 
  • Encourage your customer to have their video on. People will feel more engaged and it’s closer to the real-life environment. 
  • Don’t miss out on the opportunity to do things that some salespeople are holding back on. It’s still in its infancy and you need to take advantage of video.

What NOT to do when recording a video

Fred decided to embrace sending video emails, especially because it’s something that he preaches. He was trying to get a guest on his podcast to talk about virtual selling. In fact, he was sending a video to Tyler Lessard, one of THE experts on digital selling. So he recorded a video using Vidyard. 

Fred tried to be clever in his video and hid behind his chair, saying, “People are scared, please come on, share all of these great tips…” He sent the video without reviewing it. Turns out, he sent the video without sound. He sent a silent video of him cowering behind a chair. He prepped for the video, reflected best practices—making it relevant and personal—but forgot to double-check before he sent it. Tyler did end up on his podcast, Fred jokingly saying it was likely out of pity more than anything else. 

It’s all about preparation and follow-through. He thought about what he was going to say, how he was going to say it, and the purpose behind it (what he wanted to achieve). It was punchy and short and interesting. Give yourself a moment to prepare—and execute—well. 

Resources & People Mentioned

Connect with Fred Copestake

Connect With Paul Watts 


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