316: Optimizing the Sales Day, with Steve Benson

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Thriving in routine by Optimizing the Sales Day and nothing will be forgotten. Work smarter not harder.

Steve Benson, CEO and Founder of Badger Maps, kicks off the first Conquer Local episode in 2020! Steve provides conquerors insight into how to optimize the sales day at every level, from the salespeople on the floor to sales managers, and the executive team. Steve also tells us how his failures helped him succeed because frankly, SaaS startups are hard.



George: Welcome to this week’s edition of the Conquer Local Podcast, it’s George Leith. We are bringing you some insights from a Google sales veteran. He now is the CEO of a company called Badger Maps. Steve Benson is the CEO and co-founder. He has a podcast, he has been developing the solution over the past eight years. We’re going to find out what salespeople need to be doing in 2019 to optimize their sales day. And for you field sellers that are on the street pounding the pavement, going door to door, Steve is going to bring us some insights from his career through SaaS software companies and then starting his own SaaS startup that helps salespeople all over the world with his mapping solution. Steve Benson, our guest this week on the Conquer Local Podcasts coming up next.

Colleen: Hey, conquerors, it’s producer Colleen. That’s right, I do exist. If you love the Conquer Local Podcast, then you can’t miss the Conquer Local Conference. We are heading to Montreal, June 8th through 10th at the stunning Fairmont Queen Elizabeth hotel. It’s only two days before the Canadian F1 Grand Prix. It’s the must-attend conference for companies selling digital solutions to local businesses. We have a special discount for our listeners, book by January 31st to save $100 off the already discounted early bird price, using promo-code PODCAST100. That’s a total of $500 in savings. Plus you’ll automatically be entered to win our VIP Grand Prix package of two tickets and three nights at the Fairmont to take in the biggest sporting event in the country. Get your tickets and book your rooms today at conquerlocal2020.com. Again, that’s promo-code PODCAST100.

George: This may be the most valuable podcast you’ll listen to because I think that one of the biggest challenges that salespeople have, is optimizing their sales day. And producer, Colleen sought out an expert in this space. We have the founder and CEO of Badger Maps, Steve Benson on the line. Steve, thanks for joining us in the Conquer Local Podcast.

Steve: George, thanks for having me. I’m really excited to be here.

George: I was looking through your resume, thank God for LinkedIn because it’s easy to creep people and find out everything about them. And I noticed that you spent some time at HP, IBM, Google. Your history in sales is long and storied. I’d love you to share a little bit of that resume with us.

Steve: Sure. So after business school, I was basically excited about technology and wanted to go in that direction, wanted to learn about that career path. And sales was kind of the role I was playing in the world at the time, it was a natural fit for me and it was something I really enjoyed. So I wanted to kind of combine my sales background with technology. So I ended up in IBM’s program, they have a program for new MBA students or recently graduated MBA students that they kind of… It’s a year-long sales training program and it’s kind of grooming their future sellers basically, and IBM’s an interesting place to sell because they do really big deals. They don’t do that many of them, but they’re huge and they were in a time of transition.

Steve: So I was there for… I did that training program and then I promptly at the end of that training program, I had figured out, well I had sold software, I’d sold services like consulting services and I’d sold hardware. And hardware was tough to sell, low margins, very competitive. Services was always challenging to sell, and I really liked the software because of super high margins, I made the most money for selling it and it seemed like where things were going. So then I ended up going deeper into that industry. And then I got into SaaS software after that and then I ended up at Google for a while and had a nice run there. And then I started this company Badger Maps about eight years ago.

George: Well, I bet you if we were to take a list of all the people that worked at Google and then did SaaS startups, there would be quite a few of them.

Steve: Yeah, I’m not the only one that’s, that’s for sure.


Work Hard, Work Smart – Be Efficient to Keep a Million Balls in the Air

Steve: Well, I think this is one of the most important topics, not just for sellers for a lot of people in business, but especially for sellers who are comped directly on their contributions and their contributions are highly measurable. Throughout my sales career, I always felt like one of the key reasons I had been successful in sales was… And I had some luck along the way too. But I was Google’s top sales rep one year. And I attributed a lot of that to just working harder than everyone else. I was young and didn’t have a family at the time and I was able to just crank away at work. And you can either work harder or you can work smarter or you can do both. And I think the most successful salespeople are doing both. They’re working hard and they’re working smart. And when you’re a salesperson, you have to be balanced and organized and I guess as you’re saying optimized.

Steve: So you have to do the appropriate amount of prospecting. You have to spend the appropriate amount of time with your different deals and different phases in your sales funnel. And you have to kind of merge a whole bunch of deals through to close. And some people selling smaller things with a smaller price point might have a hundred deals at a time that they’re juggling. Someone who’s selling something that’s large and expensive, maybe only have a handful. But either way, it’s all about being efficient and keeping a million balls in the air.

George: The other thing that I wanted to get your take on in your experience, and I find this with young sellers, I also find it with experienced sellers that maybe kind of have a short term memory. You should expect that some of your day should be set aside for putting out fires because if you really are pushing hard and you’re talking to the right amount of prospects, there are going to be some issues that crop up that you have to deal with immediately. And that shouldn’t mean that you don’t make the calls you need to make in the day. What’s your take on that?

Steve: Yeah, I mean I think… So I believe that if… Well in my job now, running a software company, I try to keep half of my day not bricked off. So meaning like I don’t have meetings it’s empty time on my calendar. Because if I don’t have that, then I end up being a blocker to the organization. And I think a salesperson needs to have free time on their calendar because there’s going to be customers reaching out to them over email or text and Facebook, WhatsApp, the million ways they can reach out to you just throughout the day because they need things, they have questions. And you don’t want to slow the sales cycle down by not getting back to them. And so you really have to have time that you’re bricking out to respond to those customers, to deal with things, to move all the balls downfield.

Steve: I think you also have to have time bricked off for just office time. So I mostly work with… Well, I guess all I work is field sellers at this point. People who are outside salespeople and I think especially for them, they need to have bricked off time, hopefully, it’s on a certain day or the first half or the back half of a certain day a week, to just sit down and catch up on all their computer work. I feel like it often ends up being work that they do it at night or in the morning before they get on the road. But either way, you need to have that time set aside.

George: Yeah I’m a big believer, I made a change here earlier this year. I found something in my social media feed around a planning guide called the Full Focus Planner and I’m old school so I still use a piece of paper and write things down. But what I found with that was it gave me some structure where you have that morning routine, you have that morning startup, you have your day set aside. Then at the end of the day, you’ve got that shutdown, which is what do I need to complete to make sure I don’t have any balls in the air? And then how do I prep for tomorrow?… But that having that routine is really key. Would you say that that is one of the top items when it comes to optimizing your sales day?

Steve: Well I think some people really thrive in routine. And if you don’t have a routine, you have to spend cycles making sure nothing’s being forgotten. And for some people, they are able to have a routine where they’re able to break off every day from 10 till noon and deal with this element of their job. Other people, they have to be more reactionary just because of the nature of what they’re selling, because of the nature of their job or because they have to respond to customer requests at the drop of a dime.

Steve: So it really depends, I think it’s great if you can get into a routine and set things up to get done at the same time every day. If you can schedule your time from 5:00 PM to 6:00 PM to catch up on your emails, etc. Everything you have to do at the end of the day, that’s fantastic. If you are kind of more reactionary in your role, then you have to schedule that time and wherever you can get it. And I think that does create extra friction if you’re constantly adjusting for things. If you’re constantly needing to plan things out.


Golden Nugget for Leaders: Rely on Your Teams’ Strengths for Training

George: So as a career salesperson, you worked in a number of high performing organizations, how would you go about giving advice to a coach or to a team leader or a manager, if they’ve got those different personalities? They’ve got one personality of a rep that just has to have everything written down and planned out and they’re very effective. And then they got the cowboy running around just shooting stuff and they’re effective as well. The coaching has to be a little bit different to play to those sales styles, don’t you think?

Steve: Absolutely. I think that’s one of the first things you learn when you start managing teams of people, is that some people have different strengths than other people and you have to coach them on their weaknesses and help enable them on their strengths. And there’s often no right or wrong way to do something. There’s a couple of ways to get to the same end of meeting your goals and selling them the amount of stuff you want to sell. But, when you’re managing a sales team, I think that the key is to help the people where they need help. And there’s a lot of different skills in sales, is one of the reasons it’s such a tough job is you need to be good at 10 different things to be good at sales.

Steve: And if you’re weak at any one of them, then you’re not going to be successful. If you don’t know how to close, if you don’t know how to prospect, if you don’t know how to ask the right questions and any of these skill sets can be coached on. One trick I think that I’ve used a lot, I’ve listened to your podcast before you call them golden nuggets. One golden nugget that I like is to look at your team and make a list of all the things that they need to be good at, to be good at their job and then make this a matrix. So it’s the things that they need to be good at across the top. And then the list of who’s on the team along the left-hand side and a spreadsheet and rank all your reps on each one of the skills they have to be good at.

Steve: And then the person who’s best at each skill have them teach everyone else over the course of a couple of months. Have them do a 20-minute presentation on how they’re… Or if it’s more involved, making an hour presentation. But when the group gets together for their weekly calls or whatever, have that person teach the rest of the team how they’re so great at negotiating on this point or overcoming this objection or how they’re prospecting and attaining such a nice funnel. Whatever the skill is, have them teach everyone else. And that tends to really improve performance because no one knows the secrets and the tricks of the trade like the people in the actual trade.

George: No I completely agree with that. That is an awesome piece of advice. So this week I was at a banking convention because we’re doing a bunch of work with bankers and I have a lot of… I actually met some very, very sharp salespeople at that event. But there was one session where I had venture capitalists speaking about a venture fund that the bank was involved in. We had a gentleman who is leading a startup incubator and they were talking about you, Steve. Not in particular, but they were talking about SaaS founders and how you have to… Our CEO Brendan King said some days he’s like a Weeble. You know the Weeble that wobbles but you can’t knock them down?

George: And it was interesting to listen to these venture capitalists say, when they are looking to invest in a startup, they want to find a founder that won’t fall down. Because they know you’re going to take punches as you start that business and you want to be able to take the punch and come back and punch harder and move forward. So you know what I want to talk about now because I believe that SaaS startup founders are some of the best salespeople out there. They have to be to get their ideas sold either to the staff that they hire, to other founders that they bring on board to investors. And as the founder and CEO of Badger Maps, I’m sure that your experience as a salesperson has helped you to bring the company to this point.

Steve: Absolutely, actually I’ve always felt like having the founder/CEO have a background in sales the way I do, has been a secret weapon for us. Because I think there are few backgrounds that are better suited to running a small growing company and getting it from $0 in revenue to $1 million to $10 million. A salesperson is uniquely positioned to help do that. And not that it’d be a bad thing if I knew how to code, which I don’t, but I was worthless on helping with the product side. I didn’t build it at all, that was people I hired early on. But so it would’ve been cool if I could have been not just worthless there, but I think it was more useful.

Steve: That was a hireable skill. It wasn’t hireable to have the CEO be able to join meetings and close deals and move deals down the pipe. That was a lucky thing that we had at Badger, that I could sit down with the VP of sales of a field sales team and talk to him credibly about why our product would be able to help them sell more next year. And because I could do that credibly, it really helped us get those first large organizations on board with Badger and move them down the line.


Badger Maps Beginnings, a Solution for Salespeople

George: So what I’d like to touch on as we, as we approach the close of the podcast today, what I really want to dig into is eight years ago when you founded the company, what problem had you identified that you needed to help solve?

Steve: Well, so my whole background was in field sales and then I was working at Google on their maps team, and I was in charge of selling their maps into the Western U.S at the time. And so I’m not exactly a genius founder who came up with a brilliant, never been thought of idea. I was literally selling maps and I had a background in field sales. And I was like, field salespeople have a geographic problem where they have all these customers all over their territory and to efficiently optimize their time in the field they have to understand, where are the people that I need to interact with given where I’m already going to be? I can’t be in the Northwest part of my territory in the Southeast at the same time. So given where I’m going to be in the next week, where should I be optimizing my time? Who should I be focused on?… What is my route? And what do the schedules look like to do that in an optimal way?

Steve: And so we basically set out to take all the data in someone’s CRM system or spreadsheet, or however they manage their customer data and give it to the sales rep, in a way that can help them be efficient throughout their day. Spend their time in the most impactful way, not waste time zigzagging around town and stay focused on the most important customers. And so that’s the solution that we set out to build. And frankly, it took about five years to build it in a way that really worked effectively and is really great. But about two, three years ago, it really got to a point where it was a great tool and is really helpful to field salespeople today.

George: Well, I appreciate you sharing that because I think it’s always important when you’re talking to a SaaS founder to talk about that moment that they realized there was a problem, and that they might be able to build a solution. Also, thanks for the transparency that you’ve obviously pivoted a number of times to get something that you’re feeling really good about. Now Steve, you also are the host of a podcast, the Outside Sales Talk Podcast and I recommend it to our listeners that are doing field sales. You share some very interesting insights as well, bring on some great guests that are experts in helping field sellers. So today we wanted to get some of that insight from you to help all of our salespeople and sales managers that are on the call around optimizing their sales day. And for you field sellers, I encourage you to learn more about Steve and his company called Badger Maps and subscribe to the Outside Sales Talk Podcast. Really appreciate you having on the show today, Steve. And have a great day selling.

Steve: Thanks for having me. This has been fantastic to meet your listeners. And also I’d encourage people as you mentioned, check out Badger Maps and for enduring my company here for the last 20 minutes or so, I’d be happy to… Tell one of my salespeople, whoever you talk to that you heard about me on this podcast and they’ll give you two months free of Badger to try it out.

George: Awesome. Steve, have a great day. Thanks for joining us.

Steve: Thanks for having me.



George: Well I believe that optimizing the time that we have as sellers is crucial to being successful. And I wanted to dig into Steve’s brain because he talks to sales organizations in the field every single day. He has been… He’s got a great career resume and then he started his own company eight years ago to solve this problem of, what do field sellers need to do to be more effective? And that whole comment on you can work harder or you can work smarter or you can do both. I’m sure that folks that I have done some training with have heard me say that over the years. The other piece is making sure that you’re leaving some time for the things that just come up. You can, if there aren’t things coming up, always jump on another call and start to move a deal further down the funnel.

George: But more often than not we’re looking for those moments that we could deal with issues that are happening during the day. And what Steve mentioned is something that I’ve been noticing here over the last six months working with sales teams, is you need to be ready to help move the deal closer to a close when the prospect is ready. And you can’t really map that out by saying, okay, I’m going to talk to Jim today and he’s going to move to stage number three. Jim is going to decide when he’s ready to move to stage number three of the process, and you need to be ready to deal with him on his terms. So listen, I am notorious producer Colleen will tell you, at having the bricked schedule. And I just take pride and say… And yeah, I just get to work earlier and I just do more work than everybody else, but I’ve found over the last six, eight months that it’s doing a disservice to the people that I’m working with on a daily basis when I don’t have those little openings in my schedule where I can help them.

George: And if you’re going to be a leader and that is what is expected of you and you’re not just an individual contributor, you need to make sure that you are leaving those times open. I tell Brooke, who is responsible for my schedule, you need to protect me from myself and she just does a fantastic job of that. Colleen does some of that, protecting from myself. I love talking to guys like Steve Benson. I have a lot of admiration for people who are SaaS startup founders because it is, you need to be able to jump back up. You’re going to get punched in the face and you need to come back and punch harder as you come back up. So we appreciated his insights today on The Conquer Local Podcast. Producer Colleen has been doing a phenomenal job in getting The Conquer Local community rolling, and it really is you, the conquerors around the world that are listening to the podcast.

George: We’ve made it even easier for you to join the community by going to conquerlocal.com and you can join the community there. But once inside the community that has been developed on Slack, we’re really counting on you to drive topics of conversation. I belong to a number of other Slack communities and what I find is when we get to daily active users where they go there and they ask a question and they get a great response from other people that are conquering, that’s when this thing is really going to take off. We appreciate our users. Gilsi, our friend in Iceland from CrankWheel, has been on there. We’ve got Mike Giamprini from G Partners had been sharing some things with us. David Little, the SVP of Enterprise Sales Comporium in South Carolina. Just among some of the conquers that have been leaving, either great topics that they have found that have helped them in their career or asking questions and looking for feedback from the various people on The Conquer Local community.

George: It’s something that I’m very passionate about, and producer Colleen has been doing a great job of making sure that it’s top of mind for the people that are a part of the Conquer Local community. So please try it out, when you’re looking for advice on something that has happened, ask the conquers and see what you’re getting for feedback from that group. We’ll be back again next week, right here, wherever you listen to podcasts with another edition of the Conquer Local Podcast. My name is George Leith, I’ll see you when I see you.

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