2023 Sales Challenges And How To Face Them With Steve Benson [Episode 103]

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Are you adapting to the new age of sales?

Having a career in sales in 2023 looks very different from how a sales career looked ten years ago – and it looks even more different than ten years before that. Today, the client knows more about the product or service than ever, so how do salespeople adapt? Doug C. Brown speaks with Steve Benson, the founder of Badger Maps, about the new sales experience of 2023, how to overcome new challenges, how to consistently improve, and much more.


In this episode you will learn:

Episode’s guest – Steve Benson

CSS 99 | Sales Challenges

Steve Benson is the CEO and founder of Badger Maps, the #1 App in the App Store for outside and field salespeople. Steve is also the CEO of Badger Sales University. After receiving his MBA from Stanford, Steve joined Google, where he became Google Enterprise’s Top Sales Executive globally in 2009. In 2012 Steve founded Badger Maps for outside and field salespeople to upgrade existing CRMs with mapping, routing, and scheduling. He also hosts the Outside Sales Talk, a podcast specifically for outside salespeople, and is the President of the Sales Hall of Fame.

Visit his website: www.badgermapping.com

Steve is giving away 2 opportunities for CEO Sales Strategies listeners. The first is one month free of Badger Maps, the best app for Field Sales. Learn more here: https://www.badgermapping.com/

The second is Badger Sales University – the first month free, and the 2nd month is 80% off with code: STEVE80. Learn more here: https://salesuniversity.badgermapping.com/


2023 Sales Challenges And How To Face Them With Steve Benson

I am bringing you another amazing guest. His name is Mr. Steve Benson. He owns a company called Badger Maps at BadgerMapping.com. He is an expert in the field of outside selling or outside sales. He has a software company of good proportion and salespeople. He’s managing and leading. We’re going to talk a lot about what it takes to be successful in 2023, from what you would normally think about the challenges and the pitfalls to what you could do about them as far as up-leveling your excellence. Also, up-leveling and doubling down on certain things that you could do and how to measure and map out this whole process for 2023. Without further ado, let’s go talk to Steve right now.

Steve, welcome to the show. Thanks so much for being here. I appreciate it.

Doug, thanks for having me. I’m excited to be here.

I’m going to jump right in because you are an outside sales professional who helps people. You also have a software company which is at BadgerMapping.com. Is that right?

Yeah, badger like the animal. I went to the University of Wisconsin. When it came time to name a company, I could do nothing but say badger.

True to the alma mater.

Exactly, and mapping, not because we map badgers, but because what we do is mapping and routing for field salespeople.

Let’s talk about sales in general. You and I have had conversations on this in the past. I’ve been on your podcast, which is awesome, regarding outside sales. 2023 is coming up and things have shifted with the pandemic. There are all kinds of shifts that have happened. Salespeople now are very valuable but perceived differently than they used to be for the transfer of information or broker of information. Do you want to speak to that from your perspective?

There are several nested questions in there. First, how are things shifting for salespeople with respect to a lot of people who have declared sales dead? It is very incorrect because yes, some of it is going to be replaced by marketing. I think that people are getting information without speaking to salespeople, and that’s a good thing. It’s good that if you’re evaluating a piece of software, for example, you can go to the website and learn a whole bunch of stuff about it and read analyst reports that are available online and get a feel for, “Is this the right thing for me to be doing?”

However, you still have to engage with a salesperson if you want to get those questions answered. Product-led growth has been so big, but the biggest proclaimers of product-led growth is the concept of letting your product do the growth for you, like automatic free trials. It’s giving people everything they need to use a product and purchase a product without talking to you like Amazon. You don’t have to talk to Amazon. You only buy stuff from them.

At least in the technology world, the biggest proponents of product-led growth initially claimed, “We have no salespeople. We’re not going in that direction.” That was when they were smaller. As the companies grew, they all had salespeople now. Atlassian is a classic example of that. The bottom line is things are shifting, and you want people to, and they are getting a lot of information before they engage with your salesperson.

I’ve read that people make 57% of their decision before they engage with your sales team and the rest of the decision is made after they engage. It used to be very little of the decision that was made. They would go in knowing very little. It requires salespeople to uplevel their game. They need to be deeper experts in their product, deeper experts in their competitors, and more consultative if they want to succeed.

Today, people make 57% of their decision before they engage with your sales team. Share on X

It’s because you’re dealing with someone who is a bit more sophisticated in your space when they engage with you. It’s like you were selling used cars. You used to be able to sell it to your grandma who knew nothing about cars. Now, you’re selling to someone who may have worked in an auto dealership. They can ask about the transmission and they know what to look for. It’s not that used cars will no longer be sold by a used car salesperson. It’s that this salesperson needs to be more consultative and more respectful of the knowledge that the customer has, etc.

It makes sense to me. You got things like CARFAX and online reviews. I had an older vehicle I was rebuilding, and I could go find stuff that was going to break down on it. It was like, “This is the common thing of this old vehicle, and here’s how things happen.” You can prepare for those things.

We certainly see this in our business. We named something the 57% Project because we wanted to actively create the content that people that were in that re-engaging with us decision-making period. What are the things that they would want to see? What questions do they have? What do they need to understand? What videos would show them the things they want to understand?

We actively went about creating what people who were in that phase of evaluation of our space would in fact need. It doesn’t mean we’re getting rid of our salespeople. We’ve been hiring salespeople as the company’s grown, but when someone shows up on the sales team’s doorstep, they are more educated about what’s going on.

Statistically, it’s still 43% who want to talk to a salesperson or need to in order to make that.

They all need to. They’re 57% of the way through their decision, is what it means. They’ve got 43% further to get to the finish line.

Can we say that Peter Drucker is not correct – that marketing’s job is not to make the sales team superfluous?

I would say that is incorrect, but it’s a fun way to think about it, I guess. They sure haven’t succeeded yet in making the sales team superfluous, but since Peter Drucker said that, I think that they have moved the needle down the line. When he said that, it was probably 10% or something. Now, 57% of the decision has been made. He’s right and he’s wrong.

Going down the pike in 2023, let’s talk about some of the challenges that people are going to have when they’re putting together, let’s say, a deal now. People have access to information. It could be a challenge for somebody if they’re not keeping up with their information as well. What are some of the other challenges? I did a little bit of research online on a product. I was asking questions of the salesperson, and they were going, “I don’t know. I’ll have to get back to you.”

It demands more excellence out of a sales team and it makes it harder if you’re onboarding someone. As a new salesperson, you’re coming up against someone who’s also been researching this market and learning things. They’re not coming in cold, and you just got hired here. I hired someone, and it’s one of these things where it’s like, “We’ve got so much to teach you,” because some of the people they’re talking to are already super sophisticated in technology and maybe they buy a lot of technology.

You need to be able to not only understand our product but be able to speak to the broader ecosystem and answer questions about how security works, etc. It’s complicated. We have to uplevel our game, train our salespeople, and coach our salespeople. In the onboarding process, you got to tighten up. There’s a lot there. To finish your question, you’re asking, “What are the challenges that we’re facing in 2023,” we’re in tough economic times in a lot of ways.

We’ve got inflation, low growth and the stock market is down 20% for the year. We’re in a recession or we’re looking down the barrel. It’s very difficult to say how deep something like that will go but I think as salespeople and business leaders, we can assume that it is going to affect our businesses and we’re going to encounter some headwinds. What the headwinds will be depend a lot on the industry and what’s going on.

One thing that everyone’s going to deal with or basically everyone will deal with is their competitor’s behavior changing and in some cases, being relatively desperate. Competitors do desperate things. What does that mean? It means they’re going to do things they wouldn’t normally do in normal times. Maybe they’ll deeply discount or liquidate inventory to make ends meet. Maybe they’ll give away free consulting or other types of free value. All these things steal your customers away from you and put pressure on you to compress your margins.

CSS 99 | Sales Challenges
Sales Challenges: In 2023, there will be some headwinds for salespeople. One thing every salesperson will have to deal with is their competitor’s behavior will change. And in some cases, they will get really desperate.


There are competitors who will run into challenges in 2023 from our customers behaving differently. Encountering resistance from them that you didn’t see before around not wanting to engage, not wanting to do projects, not wanting to purchase things from you at the same rate as they were before, and not wanting to pay as much. Maybe there’s a spending freeze that’s coming in from the top of their company. If you sell the consumers and customers, there’s less money to go around or they have less disposable income because of inflation.

The people you sell to are encountering challenges from them. If you sell to professional companies, this is a great excuse for aggressive procurement offices to be aggressive. Look for the procurement officer that you’re selling to jam you on the deal, like asking for discounts but using a bad economy as the reasoning. The bottom line is a lot of things come after your margins if the economy is bad. You do have to try to get ahead of that.

As salespeople or as business leaders, one of the best ways to get around that is to start positioning things and start negotiating from your first call with a prospect. Make sure you’re asking the right questions upfront during discovery so that they and you understand the value that they’re going to get from your solution. That way, when it comes time to make a proposal or ask for the business, you can drill into the real ROI that they’re getting from the value.

They’re like, “If you’re going to spend $20,000 with us, what are you getting out of this?” You can tie your proposal to it, and then when they start asking for margin concessions that are going to compress your margin, you can point back to that ROI value and say, “You’re spending $40,000 but you’re getting $80,000. You can hold firmer on price with that confidence if you understand their business and how your product’s going to affect it. You do that from the first call.

I’ve got a whole page of notes on everything you said. I’m going to double back here. I think it boils down to two things that we need to do in 2023 based on everything you said. We need more excellence and up-level that excellence. That means we must know how to sell on value versus any commoditization that could have happened in the past to creep in.

I look at it as we’ve got to sell value on the must-haves and possible needs versus the wants, especially in B2B. Most of the time, they’re buying must-haves as a primary but I see people miss this so many times. They’re going, “You might need this if you want this.” They’re not digging deep enough to convey that information because they don’t know it. They don’t know how to sell the value based on that. That was the first thing that I wrote down.

The second thing I wrote down was, in our down economy, I have never seen this not work in any company that I’ve ever owned or anybody I’ve ever said this to. Now, as your competitors are going to be doing those squirrely things that you were talking about, Steve, I believe it’s better for us to double down now more than ever on our positioning and our marketing in the market and get ourselves more in the public square than we’ve ever been in the past because the competition will be lower.

It’s because traditionally, people pull back on marketing and sales during a down economy. I think those two things combat most of the challenges that people will face in 2023. Not necessarily all the challenges, but those were excellent points that you brought up. I agree. You’re going to get more resistance from the customer. If you get more resistance, you got to be up-leveling your skills on this thing. By the way, old dogs and new dogs are alike.

Steve, I love you to comment on this, but what I have found with outside sales or inside sales doesn’t matter. Some of the senior people get the most lax because they think, “I got this.” If you’re hearing this and you’re in one of those positions, I strongly suggest that you up-level your experience as well and upgrade your skills as much as the new person. It’s because that new person coming in, traditionally, is going to be learning all the new stuff coming in and they may up-level above you. You’re not always the top dog anymore. Steve, what do you think about that?

In a challenging economy, it’s hard to be an experienced rep, a new rep, or both. I think they do have different challenges. As a leader, CEO, or sales leader, a big part of your job is to coach and improve those people regardless of what level they’re at in your organization. One thing you can do is you can look for the things that the old dogs are good at, and you can have them teach everyone else. You can look for the things that someone who’s a new dog might be good at, have them teach everyone else and try to up-level your whole team.

When I say have them teach it, what I mean by that is identify who on your team is good at something, study them like they’re wild animals and try to figure out why. Let’s take an example. This old dog on your team is great at negotiating deals and getting them done. Try to figure out what they are doing, what they have figured out here in the last ten years working at this company that’s made them so good at negotiating in this space and about our product.

CSS 99 | Sales Challenges
Sales Challenges: Identify who on your team is good at something and then study them like wild animals. Figure out how they are getting things done and then share it with your team.


Watch them do it, take notes and talk to them about it. Once you’ve got the answers as to why they’re successful, have them in a group call, and teach everyone else on the team what they know. Salespeople are often very receptive to the other people on their team who they know are good at something teaching them. It could be a young dog, too, who’s good at using technology to drive new leads. If you figure out that they’re good at that, figure out what they’re doing and the process, get it all written down, and have them teach everyone else. That’s my thought about how to approach that.

I firmly agree. I love the analogy of looking at them like they’re wild animals. I’m like, “Badger and wild animal. Here we go.”

I’m a predictable animal, is what I am. I’ve always run into company names and I’m like, “I hate that name.” I like nouns. I like anything you can touch and feel. It sticks in the mind. You say your company is yellow sunglasses and everyone pictures yellow sunglasses. When you say badger mapping, they picture a little badger looking at a map. They can’t help it. That’s memorable stuff. Whereas if you name your company with an adjective or something, it doesn’t stick in the mind.

I think you brought something up that I want to come back to Steve because of what it is to be a sales leader or if one is managing a team, I’ve always found there are two jobs in being a sales manager. A) To grow the revenue of the team, and B) To coach and improve. Those are the two main functions. The rest are given in my opinion.

Let’s talk a little more about this coaching and improving thing because I see so many leaders of sales organizations doing a terrible job at coaching and managing, or they don’t even know what coaching is. They think, “We’ll get the team together and they’re all read out what they’re going to do for this next quarter or next month. We’ll talk for five minutes and that’s coaching in a group environment.” I found coaching needs to be on an individual basis. What about you? What have you found?

I think it can be both. Coaching, in the way that I generally tend to think about it, is one-on-one. If you’re coaching the whole team, you’re probably teaching everyone something. If you’re doing that strategy that I outlined where you’re having people on the team teach others, I guess that’s more teaching than coaching. Coaching can be a lot of things. It’s so important in tough times and even in good times. A great manager is a great coach and spends half their time coaching and improving the team.

A great manager is a great coach that spends half their time on improving their team. Share on X

That doesn’t have to be sitting down and giving them direct feedback or anything. It can be a lot of things. It can be a pre-call strategy in sales, post-call debriefs, joint calls, ride-along, or going over opportunities, opportunity-specific coaching where you go through the individual deal and strategize about it. Any interactions like that count as coaching and they are often one-on-one, but anytime you’re up-leveling your team, that’s what great managers do. Also, it’s important to think about what is coaching too.

A great coach is not someone who says, “I need you to do better.” A great basketball coach doesn’t say, “I need you to score more points.” You can’t say, “I want you to get more sales.” A great coach says, “We need to score more. I’ve noticed when you’re dribbling on your left-handed crossover, if you led with this foot instead of that foot, you’d get the jump a little better because you’d cut off the defender. You could drive to the basket and do a layup.”

That’s great coaching. It’s specific and breaks down what the person is doing. It’s, “When you’re negotiating, do it like this. When you’re sending out emails to generate leads, I noticed it’s like this. What if we tried it like this?” It should be specific and also be appropriate. A great coach has to think about, “In this industry, this is what’s going on. On this team with this person, this is what’s going on.”

CSS 99 | Sales Challenges
Sales Challenges: Coaching should be specific and appropriate. A great coach has to think about, “In this industry, this is what’s going on. On this team with this person, this is what’s going on.”


You’ve got to tailor it. Is it negotiation they need coaching on, or is it generating leads? In a tough economy, qualifications can be valuable. They are spending their time on things that will convert. It’s easy to have your pipeline be the same size when the economy’s bad, but what’s coming out of that pipeline if your close rate has gone down because people don’t have money? You need twice the size of the pipeline to get the same output. That’s my thoughts on coaching.

I was writing it down and summing up what I think you were saying. Coaching is about changing behaviors, actions, and mindsets to improve and optimize what’s going on in that individual’s life as well as the overall team going there. I wanted to push on this subject matter because I see so many people who are claiming they’re in a leadership development role, but they’re not doing the development side. They’re pushing numbers and paper. They’re making directives. They’re doing this and that.

Coaching has been shown across all statistics to improve people’s ability to perform as long as they’re coachable. Thank you for bringing that up. I want to shift a little bit. Let’s talk about some specific tools, maybe geographic tools. Let’s focus on people who are selling like outside salespeople because a lot of people reading this are outside people who are selling, whether they’re the owner of the company who is still selling and they’ve got a team of people, they’re a solo entrepreneur or even own a huge corporation. What are some of the tools in 2023 that people should think about from your perspective?

In the area of mapping and routing tools for salespeople, there are a bunch of different categories of this. There’s the business to business sales mapping tools. For salespeople that are selling to businesses, that’s what we do. That’s what Badger Maps does. Salesforce Maps does a very similar thing. Map My Customers does a very similar thing. Also, LeadPlotter and MapView. There are a bunch of people in this space.

If you’re in a medical device, pharmaceutical, or construction company, you sell to businesses face-to-face. Those types of B2B sales mapping tools help you figure out who to focus on, given the constraint of where your rep physically is in the field. It’s how to build out their day, how to schedule it, how to route it and how to understand what’s around me right now. If this meeting gets canceled, who can I go and swing by in the place they live? Those can be valuable efficiency tools because if you’re getting 20% more meetings and driving 20% fewer miles, it’s because you’ve had this tool to think out your day. That can be valuable.

That’s one type of sales mapping tool. There’s also business to consumer. It’s not B2B like us, but there’s the business to consumer mapping tools. It means that the primary people who use the tool are selling door-to-door to consumers. They go up to people’s actual homes and sell them things. We’ve done some things like residential, like putting solar panels on people’s roofs, residential pest control, political stuff, residential HVAC, and all these types of things.

The companies that do that are FieldRoutes, Sales Rabbit, OptimoRoute, and Spotio. These guys all focus on people that sell the door to door to people’s houses. It’s very similar to us, except we sell the businesses and they sell the houses. You get very similar great results out of giving these guys a tool to be more organized. It does very similar things.

Other types of software that you’ll run into are territory mapping software, like designing the software. I have 100 sales reps across the country. Where should I draw the lines between their territories? How do I break up all these states and all these ZIP codes? There’s software that helps you with that. Companies that do that is AlignStar, Xactly owns them. That’s a big sales technology company.

There’s AlignMix. Salesforce Maps has a product they have for that as well. Map Dev, EasyTerritory, and all those guys help build out your territory for you. There are also geoanalytics. I should also mention that. That’s an important mapping and geography type software company that’s helping you analyze data on a map. Let’s say your marketing team needs to do some analysis on how to segment customers, figuring out where they want to run and where or what geographies they want to run certain types of ad campaigns in.

Where do we want to open up our next store, or what are the demographics in this area versus this area? What does that mean for us? Companies that do that are Tableau, which is a pretty big company that does lots of types of analysis, but they have a nice geographic product. eSpatial, Geopointe, and Mapalytics do that.

That covers the sales mapping software as far as I can think of. Also, that’s the area that I know a lot about. Broader than that, and we could talk about technology for hours, what CRMs people could use, and all that but email marketing. There have got to be 5,000 marketing technology companies at this point. There’s a lot to do there.

I want to come back to sales mapping. A lot of small and mid-size companies don’t do this at all. I don’t even think they’re aware of the benefits of it. What’s your definition of a sales map or process mapping?

It could be any of those things I mentioned, B2B or B2C. It could be building out the territory or doing analysis, but a small company can benefit from this the same way a large company can. I guess a tiny company doesn’t need to break up sales territories. If you’ve got three sales guys covering America, it’s obvious how to do it. Half of our customers are single seats. It means one person buying our software. It could be one sales rep in a big company. It could be one guy who’s running a one-man business.

CSS 99 | Sales Challenges
Sales Challenges: Sales mapping could be building out a territory or it could be doing analysis, but a small company can really benefit from it the same way a large company can.


You probably don’t have a CRM if you’re one guy running a business. You don’t even have to integrate it. You take your spreadsheet and upload it into a system like this. I’ll use us as an example. If you’re running an outside sales motion, you upload your customers and prospects into the tool, and now you can gather information into the tool when you’re out in the field. You can build a route, figure out who to focus on and use your computer to do this. You can use your mobile device, like your phone or iPad, when you’re out in the field.

The motion is to get the data in there. Now that you’re viewing it on a map, you can start figuring out, “Of these thousand people, who should I be focused on in the next week, given that I know where I’m going in the next week? Let me zoom in on that area. Who’s here and who’s important that’s here? In what order would I want to see the enemy? It has a scheduling and routing tool. You can build a route and optimize the route. You can take your finger, draw a picture on the screen, circle the things you want to add to the route and it automatically builds you an optimized route for it. You can set the meetings around it.

Depending on your motion, sometimes you’re swinging by places. If you’re selling to dentist offices for example, maybe you’re swinging by or dropping off brochures hoping to talk to the dentist. If you’ve already got a relationship with them, you’re calling and saying, “Can I come by at 4:00 on Thursday? Are you free?” That’s how a business person would use that software in their sales motion.

The reason I brought this up is because we started with, “What can I do in 2023 to improve, optimize and move forward?” Let me put it this way. If somebody’s evaluating steps, processes, stages, and data that’s coming through, small company, mid-size company, large size company, when we’re evaluating that, we find patterns of success within that evaluation. We find things that we’re not supposed to be doing as well in there.

I’ve been into companies where 17% of their clientele is buying and the other 83% is not, but they’re so focused on the 83% versus us taking the 17% and selling them more. When we did that shift, for example, they doubled in size because they went back to this, but if we’re not evaluating these steps, these stages, the data points within.

That’s why I wanted to bring up sales mapping because it’s something that a lot of people don’t think about because they think, “It’s not relevant to me.” If we’re going to get better in 2023 and we want to get better than our competition, be more effective and up-level, it starts with analyzing the data points that are going on within the stages and steps of the sales processing and the clientele that we’re serving.

Also, find plays that you can run. It’s like, “This type of customer, it’s my larger customers. It’s my smaller customers that are purchasing this product from me but aren’t purchasing the sister product that goes along with it. Anyone buying this from me is buying this from somebody, and mine goes better with that. How can I get in front of them and upsell them into buying this from me as well and being able to discuss how they fit together.”

It’s figuring out those plays like, “Where are the industries that need this, need this upsell or need this additional service? Where does this play well?” It’s figuring them out, identifying them, getting in front of them, and prosecuting them, whether it’s with a field sales motion, an inside motion or depending on how you go to market.

Sales mapping is all about figuring out plays that you can run. Knowing which industry really needs your service. Share on X

Steve, I want to thank you for being here. If people want to know more about the company, sales mapping, and yourself, where do they go?

If it’s the company or field salespeople or they are out in the field, they would definitely check out BadgerMapping.com. It’s a very useful tool in a lot of ways to do a lot of things. If they’re looking for me, the best way to find me is probably through LinkedIn. You can do a Google search of Steve Benson Badger Maps. It will pop right up. That’s the best way to find me or the company.

Steve, thanks for being on the show. I appreciate you being here, bringing in your A-game, and helping a lot of people on this episode.

Thanks for having me, Doug.

What are you going to up-level? What are you going to create more excellence on? I’ve got a ton of notes here. If you’ve been in a field for a long period of time or you’re starting out, treat 2023 as a new process because technology has moved on and it’s grown up. You’ve got to grow with not only technology but what the shift is happening in the sales arena. As we talked about, 57% of the decision is being made before you even get to talk to somebody anymore.

How are you positioned to handle that in your life if you are not constantly up-leveling or building excellence into the process? Believe it or not, over time, atrophy will kick in because other things are moving up. Competition is moving up. Whether you think you have it or not, it’s there, and it’ll continue to keep this process going for a longer period of time.

With that being said, write down what are the top five things you’re going to do in 2023 to move your career forward in your business, outside sales, inside sales, solo entrepreneur, or major corporation initiatives when it comes to growing your revenue. If you love this session, give it a five-star review, please. If you want to check out the software, reach out to Steve.

Do not discount sales mapping for your particular company. It can reveal a lot of great uncovered or hidden revenue and profitability for you when you utilize a tool like that in its best form and it’s not that hard to do. If you love the show, please give it a five-star review, as I asked. If you have a subject matter that you’re an expert on or you know somebody that is an expert on it, If you want to maybe be a guest on this show or have your associate, friend or whoever you know be a guest on this show, send us an email at YouMatter@CEOSalesStrategies.com. We will answer one way or another.

If it’s a fit, great. We’ll invite you. If not, we’ll tell you why not. If you want to get yourself through the top 1% in selling and earnings in 2023, you want to learn how to do even disciplines like following up better and automating processes like this. If you want to have a 1% earner on your team and you want some assistance in doing so, reach out to me at Doug@CEOSalesStrategies.com. Let’s have a conversation and see what’s right for you. Until next time, go out and sell something. Sell a lot of it, sell that out of profit, and play win-win. Make someone happy, make yourself happy, and to your success.


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