For most entrepreneurs, building a sales team is an afterthought. Small business owners tend to carry the entire weight of their business on their back, playing the role of CEO, COO, and CRO with marketing management sprinkled somewhere in between.
When they finally reach the point where they need to scale their company, many founders think they have no choice but to add Sales Manager to their list of titles.
The problem? Sales management requires expertise, strategy, and an immense amount of time and energy to be successful. Many founders do not have the sales experience to be an effective sales leader and their sales initiatives fall short because of it.
How can founders ensure that their scaling efforts are effective the first time around?
On this episode of Evolved Sales Live, host Jonathan Fischer sits down with Steve Benson, founder and CEO of Badger Maps, to discuss the steps founders can take to successfully transition from founder-led sales to team-based sales without skipping a beat.
Don't forget to follow us on LinkedIn for more engaging sales insights and discussions! Happy watching!
Steve Benson is the CEO of Badger Maps, Inc., the #1 app for route planning that enables field sales teams to manage their territory by combining Google Maps, data from their CRM, route optimization, schedule planning, and lead generation. He is also the host of the Outside Sales Talk Podcast which is dedicated to helping outside salespeople improve their skills, reach peak performance, and crush their quota.
Check out the transcription of this webinar episode below!
Jonathan Fischer 0:04
It's time once again for evolve sales live. Welcome back. I'm Jonathan Fisher. Many company founders also served as the Chief Revenue Officer for their companies. But with growth comes the need to scale. So how do you do that? How do you begin to transition from the founder doing all the selling to having an effective team that can take over that role? Well, we've got the perfect guest to help us with that today. Steve Benson is a highly successful software company founder and CEO, holding a degree in geography from the University of Wisconsin. Steve earned his MBA at Stanford and went on to found Badger Maps, the number one app for route planning and scheduling for outside sales reps. As the guy who's been there and done that Steve's got a ton of insight to share, which has made him an influential thought leader with over 25,000 followers on LinkedIn. Steve, we're excited to have you on the show today. Welcome.
Steve Benson 0:55
Well, thanks for having me, Jonathan. I'm really excited to be here.
Jonathan Fischer 1:00
So like I said, You've been there done that. And it might be fair to say you took the direct route in business pun intended, that tell us a little bit more about your journey of becoming a company founder. What inspired you?
Steve Benson 1:13
Absolutely, yeah, the the, you know, so I was, I was kind of scratching my own itch with this company. So meaning my background was in Field Sales, and, and I, so I understood the problems that field salespeople face. And that was really the what kind of caused me to start trying to solve these problems. It also really helped that, you know, it's obviously a mapping and routing software. And my last role was at Google working on the Maps team. So it was kind of a natural fit for me. And so I wouldn't say I'm a I'm not a creative genius. It's just really the problem and solution, were kind of in my face. Yeah, that and obviously, you had quite a passion and interest. So it all just aligned for you. And I'm sure that the name Badger Maps is completely coincidence. Absolutely coincidence. coincidental. It has nothing to do with where I went to college with University Wisconsin is, so I am a badger.
Jonathan Fischer 2:09
That good stuff? Well, I'm a fellow big 10. Guy. So that's a good thing.
So let's jump into our topic little bit here. I mean, like I said, in the intro, you've been there done that. And company founders. A lot of them do make great salespeople, they're going to be the chief evangelist for their own product. They've they're the one that has the passion to get this thing rockin. It's not always the case. But there's a large percentage where that is the case, there comes a need to transition as you grow, you've got to scale that means a team. So let's talk a little bit about that. What do you think are some of the biggest let's let's begin with the problems that founders encounter. You've, you've been there so you can share from your personal journey, you can share insights that you've gleaned over the years. What are some of the challenges when you're at that point where okay, this thing's This thing's working. This has got legs got some revenue positive here, right? But we're feeling that need to transition talk to us about that.
Steve Benson 2:59
Yeah, and then I think that moment, there's not one moment in time when you wake up and you realize, wow, today's the day I've got to hire a salesperson, it's, it's, it's often a frog in the pot of boiling water situation where you're just like, how much time did I spend doing demos last week, it feels like a lot. I feel like I did lots and lots of demos.
And there's lots of little areas you can look for, for efficiency. When you're when you're first starting. I remember my first my first big efficiency job. I was, I was doing like six demos a day, which is like a good chunk of your day to it. I was like, what if I made a video of me doing the demos,
put that on the website, then fewer people that asked to see the demos? And I think there's lots of things like that. And, you know, I guess my first thought about founder led selling is that it never really ends. Right? You will I think it's important that the founder is always involved, both with the sales team, and and also with the customers. And also even even with like a support team, you want to have your fingers on all the customer touch points in an organization.
About the founder, you know, you can have two founders at a company, you can have one founder, you can have six founders, but someone has to be someone who has a seat at the table when you start the company needs to be in that customer facing role. And what I mean by seat at the table, I mean, they they are in the conversations that are directing with product skilling. You know a lot of startups don't even have it that are that early don't have a product manager yet. So everyone's kind of acting as the product manager or the VP is that whoever's running engineering is acting as the product manager. But you really, the person who's talking with the customers every day needs to needs to have enough clout in the organization that they have their voice heard. And if none of the founders
have that kind of DNA and the plan was to just hire a sales rep right away, you know, what you see sometimes, right? You know, three engineers start a company, and they're like, who's gonna sell this thing, let's hire a sales guy.
If nobody has that DNA, you have to be, you have to be very careful, because you, you really have to give that person a seat at the table and listen to their voice. Because sometimes the things that they're saying you don't want to hear, but it's like, well, the customer is seem to be asking for this thing that we're not doing. And you said you didn't do but I think that's the thing that's gonna make them purchase that we thought was this, but it may not be that. And so I think you know that that's a, that's a very important thing to keep in mind, as you kind of approach this, this magical time that you're talking about when you're like, how do I actually scale a sales team? I think I've got the, you know, I've got my first 10, or my first 100, depending on the account size, from a value perspective, the, you know, I've got my first customers, how do I move down the road now from just me doing this all day to having a team of people doing this? What are the steps I take, what are the what's the blocking and tackling etc.
Jonathan Fischer 6:12
Well, and this is this, so you've got your own process you're using as a founder as well, which, you know, how transferable is that, though, is a lot of that just based on the fact that you are that guy, you have that personality and passion?
Steve Benson 6:26
I think it's very easy to do things as a founder that aren't necessarily scalable, people like to talk to the founder, or they're more willing to take a risk on a product that has some lumps in it, if they're if they feel like they've got to a, you know, align right into the top. And so I think you do have to watch out for things that you're doing as a founder that aren't necessarily see scalable, as you look to bring on people onto the to help with that go to market motion. You know, depending on the product, if it's more product lead, your first hire may be more on like the the marketing side developing magnets and things like content and stuff, if you're on the go to market side. But if it's more of an outbound motion, you may the very first hire may be someone who's going to help with more of a, you know,
outbound emails and going back and forth, people outbound phone calls, that sort of thing. Or it could be more growth, marketing II have a type person. So it's, it really depends on how your what your, what your experiments, as a founder have found are the best way to go to market. And
Jonathan Fischer 7:36
when you kind of think about making that first hire, well, and that's a moving target. I think that there's a lot of trends right now, where, you know, a product led approach or a feature led approach seemed to have some legs some years ago, it's become much more crowded in a given sector. And now you've got to adopt a much different approach to still get the same kind of of exposure in the marketplace. Have you seen that? What kind of transitions have you gone through in your own go to market modeling?
Steve Benson 8:03
Yeah, so we've we've always had historically had more of a magnet approach to, to our go to market motion. And once someone is engaged, they can,
you know, once they've discovered us and found interest in case, they cannot take more of a product like growth path, or that we have a free trial, and they can
really no ever need to
purchase a single field carrier, this the problems that we solve. If it's a team, they really, they historically have engaged on the with the sales team. And so we kind of have a forked path there, you know, you can go left and
be product lead growth, you can go right and really engage in kind of a more enterprise sales cycle with a with a salesperson.
Over time, I guess that has evolved to some degree. You know, when we've moved more upmarket, we do a lot more, you know, enterprise type deals now, although, you know, 40% of our revenue, and it used to be 80% is still single CD deals, right? So that part of our business has, has shrunk relative to the outbound side over time. But we still have that product lead growth element to the business. And a lot of our enterprise deals start on the product lead growth side, right. So you know, it's our sales person on a, you know, 200 person, there's two or three salespeople on the team, one of them will start using our product, then their manager sees the deficiencies they've gained, and then it kind of will spread around and kind of organically move through the organization, that manager will tell other managers, they'll get it for their team. And eventually you, you know, kind of move your way around
into where, you know, the VP of sales just heard about it. And they're talking about doing a deal for the whole company.
Jonathan Fischer 9:53
Yeah, for sure. So let's see if we can back it up just a little bit more than Steve So as having you know, been a fan
Under and it's been going for a good number of years. Now.
Let's peel back the layers a little bit more at a deeper level. How do you know maybe how did how did you know that it's time to begin scaling up building a team and taking that step? Because a lot of folks hang on to that for more than a minute.
Steve Benson 10:19
Yeah, well, and if you hang on to it too long, well, every minute you hang on to it too long, it's it's costing you growth, right? I think the first for me, the first thing to do was to get get someone that would help me scale and do things technologically that would help me scale. So
you know, like I mentioned, having a having a demo video, and that that cut the number of demos I had to do in half. And then the first hire on the go to market side was someone in marketing.
And then that was, you know, they were doing more like the Google ads and setting up the content structure and the SEO, that sort of thing. And then the first and then at a similar time, we hired someone on the to kind of as almost like a sales person to help me help scale me as a salesperson, right. So they would, they were doing a lot of the outbound all the kind of repetitive stuff, they were taking care of customers and kind of took on a customer success role. So it was really a jack of all trades. And that first hire is someone, it's a really important one, because you need someone that can wear a lot of hats, shift gears really quickly, but but also understand the product, and be gathering information that will be useful to the people who are actually building the product, helping them steer the ship. So you that those early sales hires are really important. As you scale from there.
You've kind of got your that's your general enablement guy, once once everything's working out there, and you're like, Okay, now we have more leads than I, as a founder doing founder lead sales should be handling, it's time to actually build out the team.
A lot of people, you know, make a mistake right here, right? It's, you kind of have to decide should I go with product lead growth and go bigger on that? Should I hire a, someone to lead the sales motion? Or should I hire people that are going to actually be carry the bag and carry the weight and be be the person that actually takes the product to market talks to customers, you know, salespeople basically.
I, if you have an enterprise motion, I think what you want to do is go go with hiring the salespeople before you hire someone who's to lead the team.
And just kind of take on that the leadership of the team role yourself and kind of see the founder can move from, you know, doing a lot of direct interaction with customers step back into managing the people that are and working with the people, you know, sit, you know, joining the right meetings, that sort of thing with the people who are in the go to market motion and actually running the sales cycles.
I would recommend not hiring one person at that point. But if you can, and have access to the capital hire too, because if you're getting enough leads that you that the founder is like, Okay, I've got to take this hat off, often.
You know, first of all, you're the founder is probably better at it, because they're already experienced. And so they're gonna be able to handle more leads move sales cycles through more efficiently. So when you kind of take off the hat, you lose some efficiency when you pass it. And so having to is good to even just catch the ball. But also, there's another benefit that to having two sales reps at that point that a lot of people don't see. And that is that you can compare them. If you only have one, you don't actually know what's working, right? So
are you suddenly you let's just say you hire one, and suddenly you're selling to a lot of small deals to small companies?
Is that because that's the best ideal customer profile? Or is that because that's what this person did at their last job. And so they, you know, they had a list of 10,000, small, medium sized companies, and they've done business with 200 of them. And so that's kind of their first motion was to go to that.
If things aren't going well, is it because there's a problem with the product? Is it because the rep isn't good? Is it because you've handed it off wrong? Is it something else? Is the product market fit wrong? Are you too expensive, too cheap.
Whereas if you have to, you have something to compare with, right? Especially if one if you can get a diversity of skill sets, like maybe one's more of a big deal closer, maybe one's more of a rapid, you know, motion closer and, and, and I think that, you know, maybe one is better at outbound and actually generating leads, whereas the other isn't, you can handle more of the inbound leads. So, I think
to at that point,
Wait is really the right call. And at some point in this is kind of a judgment call on the founder, depending on what what other hats they're wearing? Are they also raising money right now? Or are they also really managing the product? Are they also coding at night? You know, what are their other responsibilities? Ken? How long that determines how long? Is there someone strong during the marketing stuff that you can really rely on? Or is that something that's really, you know, I was, I was writing a blog. And every, every two nights, I tried to make myself read a blog. And if I was doing it, like two in the morning,
like, so, it depending on what other responsibilities you have, you can you can hold wear that VP of sales hat for maybe just while you have those first two, or if
or perhaps it's more just,
maybe you can hold it for five or six, and then bring on someone, but I think, you know, bring, at some point, you're definitely going to bring in a lead to that team, whether it's after you've hired those first two, or after it's, you know, five or six, but you're in and then they're going to continue to scale it from there. And they can take over the hiring decisions that the blocking and tackling of the sales process the managing of those of those employees, and that that's really a great time for the founder to step back. But still, I think be involved with with the founder led sales and that you're still you're still parachuting into important deals, you're still, like involved in commerce, I think it's important for the founder to talk to sale all the salespeople on a regular basis to try to get a feel for what deals they have what their pipeline looks like, what are they hearing from customers, there's, it's
both your CSA team and your sales team are really important touch point to understand what's going on in the world with with your, with your customers with your product in the field.
Jonathan Fischer 16:46
So you mentioned a lot of really good nuggets in in that Steve, one of them is hiring more than one person. I've heard that again and again, from successful founders, that it's good when you begin to hire for sales. And I've heard some say at least two, even up to three.
talk just a little bit more about the advantage advantages of that you mentioned one, which is that they are going to be bringing bringing different backgrounds, they have a different either, you know, their own contact list or their own experience or what have you a book of business even depending, and that's going to structure into their their results, which may or may not line up with the best results for your company. That's interesting. So you have some different, different CVS to pull on and all of that that comes with that. Are there other reasons why having multiple team members? As soon as you begin to build the team don't build with one bringing a couple of folks, are there other advantages to that?
Steve Benson 17:39
Yeah, I think the biggest one is that you, if you only have one, it's harder to learn and understand if what you have is working or not. And the diversity of of, of, of reps. I mean, a they're competing. And that's good. Someone in the notes here, I mentioned healthy competition,
you know, in the chat there.
But I think it's more than just them competing. It's also if you only have one you can't learn, Hey, what is this working? Because we're awesome? Or is this not working? Because you don't know why something's working or not working. Whereas if you have two people doing it, and it's working for both of them, then that's great. Or if there's two people doing it, and there's something's not working for both of them. That's, that's, that's a great signal. So suddenly, you you know, it's like in statistics, right? You have to have a certain number of things in your sample size, right? I think, yeah. You know, or else Or else you don't have good data. And so it's, it's a sample, a sample size of two, is exponentially larger than the sample size of one. I don't know how to express that with math. But that makes sense, though. Yeah, it's a lot bigger. It's also the smallest unit of a sample, right? To be a data set, you must have at least two data points. So but it makes sense, it makes sense, because you've got all of their combined activities and things. So now you have something that does make some some statistical sense that you can build on obviously, it's small, but it's a starting point.
What else? I mean, are there other advantages to having two people is their sense of competition? Speaking of some of the comments from our listeners? Yeah, I think I think competition always comes into play and it can be in a healthy way you can you know, competition among sales reps can be can be really valuable. They can learn from one another different people are, are good at different things. And like I said, you can pull two different resumes that have kind of that are, you know, different animals, right? So you can have, you know, your hockey player that weighs 250 pounds on the ice and you can also have one that weighs 140 and is fast and really can handle the puck, right? So it's you can have different animals out there and and they can teach one another and help each other and also pick up different roles in the team. You know, it's it's not it's different to be,
you know, a five person company than a 400 person company and if
Jonathan Fischer 20:00
First Company, everybody wears a lot of hats. And so if you have two people with the exact same skill set, they can they can help out in a lot of other ways, too. Yeah, for sure. That's another big consideration when you're in fountain, a founder and startup mode, people need to be able to juggle some things where to multiple hats, that makes a lot of sense. So I want to ask questions on either end of this. So we're kind of midway through, we've talked us into, okay, we begin to build a team. So here are my questions at either end. You are not trained in sales from your academic background. I mean, your Masters in Business Administration, you get a little bit on that. But you don't didn't come at this as a sales guy, a lot of founders do. Especially the ones where they are the main seller.
Steve Benson 20:41
What does that entail for you? What How did you get good at selling? Obviously, I'm sure they like I said, I know, they mentioned that Stanford, they know a thing or two about business there at Stanford, you but your personal journey? It wasn't awkward for you? Because you do you have this other passion that you brought to the table? Well, I think, you know, it's a funny thing about sales and modern marketing and revenue, right? Like, you know, in school, they teach, they don't teach sales really, at all, I think they're, you know, there's a, there's their classes, at least at Stanford, there were classes on like, how to manage a sales team, and like from a quant how to how to build a, how to build a comp plan, stuff like that. But there was nothing really on, you know, the blocking and tackling of sales, the skill sets that you that are required, you know, I don't think overcoming an objection ever came up, right? Certainly, the more of the trade element of it, you know, the the craft was never discussed. And even marketing I wouldn't say is the stuff that there, at least when I was in school, and granted, I mean, I was kind of probably at an inflection point, like I graduated in 2006. So like, the internet was just still kind of starting, right, like from a marketing perspective. And but we, you know, our marketing classes were very, like, strategy, Coke versus Pepsi type type stuff, right? It wasn't, here's, here's how to manipulate SEO, here's how to drive. Here's how to do content marketing, here's, here's what field marketing, here's what you actually do, and Field Marketing, like, it was none of that. And so, I think,
now my personal background, you know, that was my educational background. But then after, after I did that I went to IBM, in that was in a sales role. And that was at a software company called autonomy, they got bought by HP that was in a sales role. And then at Google, I was also in a, in a field sales role. And so my background, my academic background was business but the you know, and charts and graphs, but
I, I'm not much of a stock picker, I'm actually more of a sales guy. And, and so that's what I that's what I was doing in my actual career, and that, that was really invaluable in starting a company because the skills that you pick up in sales, the listening, the asking the right questions, the motivating people to actually do stuff, the you know, the follow up all the, the blocking and tackling of sales skills are also the sorts of thing that things that you do when you're doing product development. And,
you know, a salesperson, it's a natural role for them to find hundreds of people that are interested in chatting about a product that doesn't exist yet once and asking, Hey, so once, if this sounds like it's interesting to you, if I were to build something like this, would you be Would you Would that be something that you'd be interested in purchasing for this amount of money in the future? Like, you know, I had hundreds of people lined up before badger was, was still just a twinkle in the engineers eye, you know?
Jonathan Fischer 23:43
And I had a lot of people that were like, yeah, yeah, when this comes out, we want to do this. And so it was a really sales was a really invaluable skill set for me, starting the company. Well, I mean, it sounds almost like he got a real world sales bootcamp to do what you were doing. You brought your passion to the marketplace to see, hey, you're excited about solving a potential problem. Talk about people who potentially would have those problems and said, Hey, would this solution makes sense? I mean, you were you were selling, right. And you were building a building a cohort of users, which is also really great Agile methodology. By the way, I don't know if that was intentional or not. But for any other founders, or maybe aspiring founders out there, hey, how much better to know that there's buyers before even build the thing? Right. So it sounds like that's the the course you took with badger mapping, Steve. So you, you saw the needs, move back into sort of our timeline only about the other end, as I mentioned a moment ago. So you you learned some bit some good blocking and tackling as you put it in selling largely through the just the function of getting this thing going. Then you knew there was a time to transition and get the team started.
You mentioned about the CEO, still retaining an important role there. Talk to us more about that. So you've got sort of a burgeoning team. They got these very backgrounds, you're getting some revenue coming in. What are some really good next steps from there to make certain that this thing's going to scale? Even if you want to go take a three month break?
Steve Benson 25:02
Well, you just don't get to take three months.
Jonathan Fischer 25:05
Okay, that was a bit of a joke.
Steve Benson 25:12
experiment? Well, you know, actually, I mean, you know, and I'm,
I'm 11 years in now. So this, you know, we're pretty pretty far down the road. But I did take two months off when I, when I had a kid earlier this year. So, you know, it's been a little paternity time, but so you, you eventually, eventually you do get to step back, right and not, you know, and not have day to day. And you know, and I was available to people, they call me, they know, my cell phone. But, but really, they, you know, there, there was very little that I did, I would join the group calls. But that's just mostly because I was bored. But, like, I, I didn't have a lot of things that I needed to due. But I think early on, the things that
as the founder that's passed, kind of passed the responsibility of revenue to a group of people.
I think that you do want to stay involved. And it's important for, it's important for customers, they want to be, they want to feel like they know the founder, they want to have a line in there taking a big risk, you're a small company, you could be out of business tomorrow. I mean, we've seen big companies go out of business.
And so they,
I think there's a lot more faith if they, if they've met you, and they know you and there are things that a founder can do that other people can't do in terms of like, you know, you know, they feel like they're talking to the, you know, someone with power in the organization and get things done, if they need something done, they can they can get it. And you know, I've heard stories of,
Unknown Speaker 26:51
of Marc Benioff even today shows up at the at the big the big sales meetings like that, like he, you know, he flies into town, and he gets, he gets on probably a private jet, but he gets on a jet, and flies, flies around the world to meet a really important customer or a really strategic customer. Or, and, you know, maybe he does that because he enjoys it, and to keep his fingers on the pulse of things of what his customers want. But also, maybe he does it because he wants that revenue he wants to and he feels that his presence raises the probability that revenue is going to come in. So I think there's there's a big role for the founder, even even, you know, once you're, you know, a fully at scale public company, I think there's still that you can still bring something to the table on the sales side, there still is that Chief Revenue Officer hat that you're going to need to be able to wear as an effective founder in most in most instances, I've heard that from so many successful leaders, it's definitely evolved, it's going to change, it can't by just just functionally be a day to day thing. For most, however, it's still an ongoing role, for sure. Well, let's take just a brief pause and remind our audience members, we're going to get into some q&a here in just a few moments. So go ahead and send in some further questions. We have a few here listed that we're going to jump into. But we're gonna we're gonna have some q&a. So send them along, we want to have some interaction with our live guests here at this live event. We're glad that you're with us today.
Jonathan Fischer 28:12
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So Steve, it's been a fantastic conversation with you. It's already blown by I can't even believe it. I want to I want to give you the opportunity to share with listeners, you've already got a big following. You're kind of a burgeoning thought leader, at least in social media, what's the best call to action? I mean, we've got all kinds of people listening, obviously, the Badger solution is great. And then how can they contact you personally and tell us about that? Yeah, best way to contact me personally is either at Steve at veg mapping.com, or that's my email or just on LinkedIn. If you just search Steve Benson Badger Maps, I'll pop right up.
Steve Benson 29:22
If you're in Field Sales interested in the company, the best place to do to learn more is just go to badger mapping.com The website and check out what we do you know routing mapping, and it's generally a tool for field salespeople outside salespeople to to make their lives a lot more efficient. And so we're kind of a leading player in that space.
But yeah, the other the other thing that I'm up to right now, but you just came out with their second product this year, and it's a sales training product. So it's called badger sales University.
And that's, it's kind of like Hulu or YouTube or mass
interclass Are you know, but it's only sales training videos and it's you know, it's a, you don't have to pay a bunch upfront, there's a free trial, that's 29 bucks a month. So it's a fun way to learn,
learn stuff about sales and become better for a reasonable price for a team.
Jonathan Fischer 30:16
Very cool. So a very practical solution and some great training to go along with it as a value add, I guess, with or without the app then sounds like they could do the university and or the app separately? Yeah, they're two separate products. So they're not nice or you don't you don't have to you don't have to do them both. So ones just for Field Sales ones for all sales. Okay, well love it. Someone, some LinkedIn user told me they need to stop badgering the guest. So
hey, listen, he likes it. I do. That's what I'm here for.
Well, that makes a great segue into the q&a. So let's jump in. Steve, we have a couple of questions here. Let's hit Michael's question right out of the gate. He's wondering what are some of the top sales coaching questions to ask your reps? That's a great question. When Hey, you, your founder led, you're trying to get them up up to speed talk to us about that?
Steve Benson 31:08
What are your top Coaching Questions to Ask your reps? Well, I think that the best coaching comes from, you know, kind of riding along with reps, whether that means in the car, if they're in the field, joining their phone calls, or listening to their phone calls with with those types of those types of programs that do that. But I think, you know, seeing seeing them interacting, and then giving them feedback is one of the best ways to to coach them. You know, I think, talking through deals, you know, what's talking about the next step, but making sure they understand, you know, everything they need to understand to nurture a deal to fruition, I think, you know, any
kind of poking around for holes in the story is and then figuring out why those why the hole is there, and then coaching them around that I think is, is one of the more powerful ways to figure out what to coach people on. So a little bit of postgame.
Yeah, I think in general post post game, I mean, not that, you know, pre call stuff, and kind of making sure they have a plan and kind of, you know, talking to the plan isn't valuable. But in terms of real learning, I think
a lot of times if you do the real learning after you mess up, yeah, right.
Sometimes the message will pay you even more than when would have on a given day. Right? Yeah. And, and it can even be on the phone, it can, it can be real time, you know, over I am or I had a boss at Google who was a great coach, and he would hover over the mute button. And I would start talking or go to start talking, he would hit the mute button and be like, Listen.
That's great. That's great. I love it. So here's another good question. We'll stay with Michael for a moment. He's wondering about mirror and matching. So some of the old, maybe NLP esque type tech techniques and tips and tricks of the trade that many salespeople have sworn by, over the years is the time to swear at them instead of instead? What are your thoughts? I mean, I think to some degree, you want to you want to match your client on on a lot of ways and kind of you know, it's not always possible, but I just I wouldn't call it hokey. But I think there are also bounds of professionalism. You know, yes. About yelling, and should you yell back louder? You know, I think, you know, I think it that depends, I mean, I avoid yelling and in trying to generate leads, and sales situations, but I guess I've never had that happen either, though. But certainly, like, if, if you're sitting down, if you're in this industry, by industry to write, like, if you're sitting down with
someone in Gen Z, you should probably be a lot softer than if you're sitting down with some 64 year old man that, you know, starts the conversation like yeah, what the fuck are we doing here today? Like, if that's the
Jonathan Fischer 34:03
if you're you want to you want to start behaving very differently in those two different situations. Yeah, and I think mirror matching probably has some, some edges around it, where it's useful versus not useful. Someone's yelling at me, I'm gonna get quieter. I'm gonna like it so quiet. They have to be quiet to hear me. But that's a different thing. That's a good relationship strategy, too. Yeah, exactly. Exactly. Hey, Alexis, question from Rob Walker. He's asking, you know, if you aren't a founder led model, could it actually be there's some downsides, potentially to the team? And I don't know what the for sure is getting out. But I've got some ideas popping into my mind. What are your thoughts, Steve? No, I think absolutely. And that's a great point that you know, and not just in sales, but a founder. You know, when there's three people you own everything and you're the manager of everything. When you have 400 You had to let go of basically everything and now you just are involved in very little and
Steve Benson 34:58
just making sure that
presentations with delete the whole team are fun and interesting and engaging. Yeah, it's a very, you're, it's hard I think to to go from, you know, zero to 1 million, and it's kind of, you always have to be a different person to go from 1 million to five first, and you have to read a million, and you have to reinvent yourself, again, to go from
five to 15, and then 15 to 100. Right, these are, you know, it's a different human that, that runs all this stuff. And a lot of times you swap out the human because you know, you don't scale. And it's important to know, in a startup, hey, maybe maybe more value is created if I hire somebody to do the to do this next stage.
So I think that's a risk in any in any area, it's especially a risk in sales, because you can become a choke point on deals, if you have to touch everything and be involved in everything, then, then that's no good at our stage, and you know, we're a 75 person company, my involvement with the sales team is to I have a monthly meeting with each sales rep to discuss their deals and just kind of talk it through, I rarely join.
I rarely join customer calls, but I will, because I want to keep my finger on the on the pulse
customers or prospect calls. Sometimes like you, like I'll parachute into, like negotiate a deal, because a lot of times like they want to bring in their, you know, CIO or CFO or some some person who negotiates and then we're supposed to bring in our executive and that's a, that's a good role for me to jump in on things.
But those that kind of, that's kind of all of my interactions with with the the team.
Jonathan Fischer 36:45
Well, that's parent, and sometimes it's worth it, right? You gotta go peer to peer to make some of those bigger deals happen. That's great. And to me, I'm certain you still take care of your person, whoever was the point headed up the deal, right? You're just getting bringing it?
Steve Benson 36:57
Yeah. So that would make the respect to that much more, right, that you got it done. And they, you know, it's a win for everybody. So that makes sense. Well, and I and it's, I think that's important that it's still there when like I don't, you know, it's important not to talk up the role you played, it's their, it's their deal, you just, you came in for some silly little part. But, you know, it's, we just had this happen, we just did our biggest deal that we've ever done, it was like a $382,000 a year deal, which is a lot for us, right? That's, that's our biggest customer. And we've got a bunch of customers pay us six figures, but that's the only one paying us six figures are the three at the front of it.
we, you know, and I did help on the deal, and I negotiated the close of the deal. It's the reps deal. That's all I did 1% of the work, right. So it's very important that you don't, you know, Puff out your chest and walk around saying, I'm the hero now. Like, you're not you're not the hero.
Jonathan Fischer 37:56
I think a lot of leaders get that get that wrong. Yeah, I agree. I'm a good leader should take the blame shares the credit, right?
So here's a LinkedIn user asking you a personal question, Steve, they're wondering how much of your own time is spent in, like, the whole vision and leadership role versus the more, you know, field officer implementing and going over the details?
Steve Benson 38:19
Um, you know, I don't, I think you do spend a lot of time painting the vision, but meaning explaining it to people and re explaining it to people, right. Like, people always want to hear what, what's, what's around the next corner? And the answer is usually the same thing that's been around the next corner for the last two years. But like, like, a big part of leadership is always saying the boats going the boats going towards the sun right now. We're going west, the boats go in that way. We're still carrying, we're still carrying beings under
that, that talking about what you're doing and why you're doing it, and what direction you're going. And you kind of it's rarely do I work on changing that direction, because the direction is always, you know, pretty similar. But you do feel like you're communicating that direction over and over again, I think. Yeah, I mean, there's that inspiration, a rule. And that kind of brings us back to the whole sales skills thing, doesn't it? Because in a way you're always selling and reselling the vision for your own company. If you're a founder, I've heard that for many, for sure. Yeah.
Jonathan Fischer 39:22
Absolutely. That's a big part of leadership. Right people I think it makes people feel stable. And it's important to know there's a steady hand on the on the wheel. Yeah, for sure. Here's a question from let's see Michael watt. Let's end on this one. He's asking what are some tips you can give to sales reps since you're working with them making sure they're successful? You know, there's these ebbs and flows in the sales cycle when looking for a way to break out of that what are some tips and tricks you can give? Yeah, I mean, you every every salesperson has been stuck in a rut before you know there had had a slow quarter or a slow year.
Steve Benson 39:59
think that if you're trying to encourage someone who in the past has done well, but it's not doing as well now it is to is to get back to basics and talk about, you know, pipeline growth developing business where, what are some strategies that that they could take? Where are some holes in the market? What are some, you know, what, what, what could they prosecute to grow their pipeline? And
you know it? And of course, you know, figuring out if something else going on, but But yeah, I mean, it is, there's seasonality and there's also, you know, rep seasonality too, it's hard, it's hard for someone, if they killed it last year, then this year, they're like, I feel like I'm working just as hard. But I don't have the big I don't have like a huge deal on my pipeline. Right. So yeah, you know, helping them helping them take a step back and figure out well, what can we do to get you get you a great deal on the pipeline? I think it's a reason why there's so many sports analogies in sales, because it is really a mental game, right? Once you've got the fundamental skill sets,
Jonathan Fischer 40:57
which of course, you got to keep those sharp, but a lot of it's just such a mental game, because start to get into your skin, people can get
almost superstitious as though they're having like a bad luck streak or something like that. Have you seen that? Do you have to kind of talk people down from that, from that ledge occasionally?
Steve Benson 41:12
I've definitely seen people get get frustrated. And and, you know, and I think there's, there's often like, especially in an organization that's quick, quickly changing which these startups always are, there's often a lot of blame of oh, well, you know, I'm not doing as well as share, she's got so many more sales reps. And so there's less, I'm getting less new leads, or you're the I think people often feel like the ground has changed, the ground is shifting under their feet. And I think you got to be really careful with things like comp plans and make sure they're making sure they're fair and making sure people making sure you're putting the numbers in the right place. Right, that's something that a lot of companies are working on right now is we're where to put the stakes in the ground for 2023. And my rule of thumb, there is kind of to not bake in growth, but let reps, let reps experience that don't bake the growth into their number, let them experience the growth in in good paychecks. So meaning like, if, if we if we sold $2 million this year, don't make their quota, you know, 240, don't don't put you know, $2.4 million in their quota, let next year, make it 2 million and let them let them go through because if you kind of bake in all the numbers into the number of people, people are always missing it. It's better to just let the bet but bottom line, I think it's better to kind of keep them keep the numbers in such a place where it's like, yeah, you're everybody's hunting with their kills Kellen. It's an uncut, uncapped, uncapped, you know, Commission's plan and, and pay people, you know, 10 to 20% of what, what, you know, what the what the company is bringing in from from a revenue perspective in that first year? Well, I liked what you said there, too. And I you hear that a lot from producers and met and having been there myself over the years.
Jonathan Fischer 43:04
You can you're really, you're really communicating a lot with one approach versus the other. When you just raise the quality, you're basically saying, I don't want to have to pay you an extra commission. Right? You kind of being parsimonious when you say, look, overshoot your number, man, great job. You're saying, Hey, I'm, I'm in your corner. I'm your I'm cheering you on? I am your coach, if that's what feels like to me, would you agree? Would you agree with that? Is that part of what you're? What the ethos is behind what you said there? Yeah, and a lot of it is psychological, because there's often more than one variable that that yields what they're going to make. And but it's like, if you it's, it's almost better to change the payout rate than it would be to pay change the quota, because then people you know, they're like, Oh, you're moving the you're moving the goalposts on me. It's, you know, it's, you have a lot of control over
Steve Benson 43:51
over this stuff, right. I think you have there, you, you ultimately, you're when you're setting plans for salespeople, you control, you know, the outcome more or less, because you can see in aggregate what's happening with the business pretty cleanly, usually.
And obviously, you're going to have the occasional crappy year or breakout year where people just make crap money or awesome money. But in general, you know, these things, at least in SAS, things tend to be pretty, a lot of times they tend to be pretty, pretty predictable. And I think it's, you're better off to err on the side of having people feel good about things and paying people well, because if you don't then turnover costs a lot on a sales team, and it's competitive, great sales reps can get a job anywhere, so you should act like it.
Jonathan Fischer 44:34
Well, Steve, wise words spoken from a guy from the trenches. I really appreciate you sharing your insights, someone who's actually been there and done it, as I said at the outset, thanks so much for being on our show today. Absolutely. And thanks to our audience members for making this show is such a success. Without you, we couldn't keep going. We've got a lot more to offer. Join us back here again, same time, same station every Friday to join us for evolve sales live. Happy to have you with us. We'll see you then. Thanks a lot, everybody.