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Quotable Podcast Episode #73: Career Development Is More Than Just Making Your Number, with Steve Benson

Host: Kevin Micalizzi, Christina Arroyo
Making the number is just the start. Join Steve Benson, CEO of Badger Maps, as he shows the immense value of helping your employees get on the right career track. By bringing the right talent into sales, you’ll increase retention, improve your bottom line in a sustainable way, and create more leaders in your company. Follow this long-term approach and everyone wins.

The right career path for you requires: 1. You like it. 2. You’re good at it. 3. There is a job there.”

Steve Benson | CEO, Badger Maps

Episode Transcript

Kevin Micalizzi: Thank you for joining the Quotable Podcast. Today we’re going to be talking about career development and really what leaders should be doing to ensure that everyone is in the right role, or at least on the right path. It’s not just about making the number. It’s about making the entire company better. Today we’re going to be talking with Steven Benson. He’s the CEO of Badger Maps. Steve, welcome to the studio.

Steve Benson: Thanks for having me. I’m really excited to be here.

Micalizzi: I’m excited to jump into it. I’m Kevin Micalizzi. I’m the Executive Producer of the Quotable Podcast.

And I’m joined today by Christina Arroyo. She’s our Visual Design Manager here on the Sales Cloud team. Welcome, Christina.

Christina Arroyo: Thanks for letting me join today.

Micalizzi: So Steve, for our listeners who aren’t familiar with you, would you share a little bit about yourself?

Benson: Sure. Well, my background, I grew up in the Midwest and went to college in Wisconsin. Came out to the Bay Area to join the tech boom.

Micalizzi: [Laughs] All right.

Benson: I started my career after business school at IBM on the sales side. And then pretty much my whole career was in field sales, which is why I started a company to help field salespeople.

My last gig was at Google and I was there for about four years. I was their top salesperson for their enterprise sales team. And then I came to start this company, and [it’s] been growing for the last six years. And here we are.

Micalizzi: Excellent. So with a lot of the sales leaders and managers I talk to, if we talk about coaching or career development, it’s actually always related to the sales or the sales process. And it’s not so much the employees’ broader career and where their trajectory goes. It’s more, are they hitting their number?

What can I be doing to help them increase that number? What can I be doing to help that sale? So I’m curious: You focus a lot more on the employee — are they in the right role? How is that career arc going to go? What led you to kind of take that approach?

Benson: I totally agree with you, and I think it makes sense that people do tend to be focused on the next quarter, the next year. How am I going to get the most out of this employee and incentivize them to be the best they can be over the next short period of time?

The reason that makes sense is because that’s how we incentivize management, right? We incentivize them to think about the next quarter. And maybe this person’s not going to be working for them on their team in five years. Maybe they’ll be on a different team. Maybe they’ll be at a different company. But I think people do tend to have a relatively short-term view on their employees’ career paths. And I guess one reason why I’ve taken a different stance on that and I try to think about things in terms of a much longer-term view is because, as the head of the company, the CEO, as long as the person is still with the company, they will be under someone in the organization.

So I really care about their career development. And I might not want them — they may be in sales today, but in two years I may actually want them in marketing because that’s what they’ve shown a predisposition for, and that’s what they’ve gotten interested in. But when they were 23 and coming out of college, they sign up for an SDR role, and so we had them in that. But then over the following two years maybe they’ve proven to themselves that they can be really good at this other thing that’s totally as — maybe it has nothing to do with what they started out in. So I guess there’s that and in that aspect that I think they may be in a different part of the company.

So I’m more incentivized to think about them and their career and getting them in the right place and getting them involved in the right things that are going to be the best fit for them and where they’re really going to thrive. I guess one thing about our company, Badger Maps — from an employer perspective, we have a lot of a tenure with our employees. People tend to stay around. In general, with a lot of companies today, I think there’s a lot of jumping around and people moving every year and a half or two years. You look at people’s resumes and they bounce around every — constantly. We have tended to do things in such a way and build the team out that they tend to stay around.

We’ve got a great culture, and people really — it’s a team — people really enjoy being here. As a result, I think that most of the people that are working at the company today will be here in five years. And so I’m even more incentivized to make sure that we’re getting them started in the right career path, because I’m thinking about where their career’s going to be, three steps out. And it’s important to me that we get them on the right path so they can be really successful.

Micalizzi: Right.

Arroyo: Yeah, and I think something that kind of startled us when we’ve been talking about sales and sales folks, and where do sales folks come from. Most people don’t go to college and say, “I want to study sales.” They’re just — there aren’t a whole lot of those programs out there. So you’re getting people from — that have studied all kinds of different things — business relations, history, philosophy. So they come to you and they sign up for a sales role, but they don’t really know who they are and what they want to do. So sales organizations are constantly talking about the fact that they have such a high attrition rate.

So how do you coach somebody to discover who they are and still keep a cohesive sales organization?

Benson: Yeah, well, most people don’t know that — everybody thinks — everyone knows that sales is really important for businesses. Most people don’t know that one out of eight jobs in America – full-time jobs — is a sales role. And yet very, very few colleges have a major in sales or classes in sales — there’s not a path to become a salesperson the way there [is in] a lot of careers, like an accountant. There are more salespeople than accountants but there’s an accounting major where they really teach you how to be an accountant, right?

There’s not as clean a path and people, therefore, come from everywhere. It’s almost more of a — when people are starting out — a personality type. Do they have the grit and the ability to communicate, both written and spoken, and the attention to detail and the empathy to be a great salesperson? And so there’s raw talent, but I think almost all of it is teachable. I mean, you could be an introvert or an extrovert and be a great salesperson. You could be — there are a lot of ways to do great in sales.

And there are certainly natural characteristics that kind of make a person better right out of the gate than another person. But most of them are very learnable.

Micalizzi: I want to just [comment] on Christina’s question because I think there’s an aspect of it … Obviously — we were talking about it —  you always have to hit the numbers. Those targets never stop increasing, which is good, because the company doesn’t grow if you’re not doing it. How do you apply that focus in trying to guide your employees but at the same time not interrupt the selling that has to happen for the company?

Like how do you balance it, but how do you approach it to begin with?

Benson: Well, I do consider our sales roles to be one of the major entry-level positions at the company, meaning I actively plan on pulling people out of that role and not having them stay on a career path that is in sales, but moving into something that might be totally different. It could be operations. It could be marketing. It could be recruiting. It could be product management. It could be a lot of things.

It’s harder to hire someone right out of college into a marketing role than it is to hire them into a sales role, I think, just because there are a lot more sales roles than marketing roles. I guess I end up often moving people into a marketing role from a sales role once they really prove, wow, they’d be great at this.

Micalizzi: Right. So you’re doing the capacity planning up front. You’re not going to interrupt that flow because you’re planning in the headcount to not only cover hitting those numbers but also to supply or feed the rest of your hiring needs. That’s what it sounds like.

Benson: Right. And a sales manager might not always like it when I take one of their great people away and put them onto marketing. But if I feel and that person feels that’s really the direction they want to take their career, and how do we determine that, right? The right career path for you I view as being a combination of a bunch of things. So you’ve got to be good at it, or we’ve got to be able to teach how to be good at it, right? So you have to be capable. And also there needs to be a job there. There need to be those types of roles.

Like you could want to be — you could be really capable at something and you’re good at it and you really enjoy it and it’s what you want to do. But if there’s not a job in it, then it’s more of a hobby, right? So like shoe shopping. There are no jobs in shoe shopping. So you could be great — you could be the best shoe shopper [laughs]. You could be the best videogame player. I guess there are jobs in that now at this point, but, well — [laughs].

Micalizzi: Totally understood.

Benson: But — so when I’m working with a young person, or really anyone at any point in their career, but I try to really focus on this early in people’s careers because you can really put someone on the right path or the wrong path.

And I look for things that they’re capable of or we could make them really good at, and that they really enjoy doing, and that there are roles in at the company. And so when I look at a young person or someone earlier in their career through that lens, as long as I can find something that is all three of those things, then I feel like we can really get them going in a good direction. A lot of people only get two of those, right? And the two they usually get are you are good at it and there are jobs in it, but you don’t like it. You don’t enjoy it, right? But you’re missing the “I like it.”

Most people — and a lot of people in sales are like this. They’re good at it and there are jobs in it. Accountants, lawyers — a lot of jobs, right? Like people — you learned a skill. You’re good at this thing. You’ve learned through experience, through education, through whatever. You are good at it but you don’t really like it. And you end up on that career path anyway because that’s what you learned. And five years, 10 years into your career, it becomes really difficult to switch. So actually, especially with people early in their career — and we have a big intern program and I try to do this a lot with them — I try to make sure I figure out what does this person really enjoy doing, what activities?

Like, what is a marketing job? It’s writing. It is communicating. It is strategizing about how do we approach the market? How do we go to market? How do we let the world know that this thing exists? Do they enjoy the activities that go along with that, or would they more enjoy the activities that go along with a sales role? And what’s a sales role? Well, it’s communicating verbally. It’s educating. It’s being very organized and having a lot of attention to detail. Do you enjoy those activities? Is it something that you want to do for eight hours a day?

So I try to have them kind of sample these different types of jobs and different types of activities. Then we’ll sit down and talk about do you like this or not, and could you get good at it? Or are you good at it already? Is it a natural fit, or is it just, it’s never going to be the right thing for you? That can really set someone off in the right direction.

Micalizzi: So as a CEO, there are a lot of demands on your time, I’m sure. Even getting us scheduled on the phone to have our initial call about this podcast was a little bit of a challenge because you keep a busy schedule.

As your organization is growing, how are you keeping this focus? I mean, you can’t be that hands-on in helping to develop every one of your employees. How are you making it part of your culture so that your managers can help to further the mission that you started?

Benson: Yeah, and I have had to pull back a bit. But we’re still small enough that I can do this kind of stuff with everyone. And I try to do certain things at scale. Like I built a little algorithm that — it’s basically a survey. I just did it — it’s simple. I just built it in Google Surveys or whatever they call that.

Micalizzi: Google Forms?

Benson: Google Forms, yeah. So a little Google Form, and then it populates a spreadsheet that runs through an algorithm and kind of — I ask people a bunch of questions about what they enjoy doing and what they like doing and what their preferences are. And it forces them to choose, left or right, and against things that aren’t necessarily correlated, like are you more creative or more analytical? And things like — you can be really creative and really analytical, obviously, but by forcing people to say, “I am more this; this is more me,” I can start thinking about sliding them into jobs.

On a scale of one to five, how tiring do you find it to talk on the phone, or to teach people things? On a scale of one to five, how much do you like sitting quietly in a room writing an article about a topic that you don’t know very much about right now? So you can tease out what types of activities someone would be good at, and then I just the algo … I just run it — basically run it through to say, okay, I’ve broken these jobs up into their activities, and I can come up with a number of how close a fit is this job for this activity. And I can do that pretty quickly, right? They take the survey on their own time.

I just look at the results and then kind of — I read — I go through the answers with them and kind of talk over with them why they chose what they did. Then we can kind of pretty quickly come to, “Well, these are three jobs that would be a good fit for you, and these probably wouldn’t be as good of a fit for you.” So I can have one of these meetings with someone and — obviously, I’ve mentored hundreds of people at this point — I can have one of these meetings with someone in 30 minutes and really kind of help put them on the right direction.

Micalizzi: Excellent.

Arroyo: But is it something more than just the survey? It’s that you’ve really built up a sense of trust in your organization where I can raise my hand and say, “You know, I — ”

Benson: That’s a great point. Yeah.

Arroyo: “— maybe I could do something else,” or, “I think I could help you here,” that you kind of left the door open to have this continuing dialogue.

Benson: And I think people also see people who are really in a great spot. I’ll actually hire someone out of college into a marketing slash sales-type role where they do some — they dabble in both, with the goal of switching them into one or the other a year down the road.

But I’ll start out with them really kind of engaging in both roles, and I’ll do that because, in interacting with them, I couldn’t tell what they’d be better at [laughs], because it’s not obvious all the time, right? And I’ve had people change their answers, too. Like this one guy came in and was like — his answers were purely, “I should be in marketing.” And I was like — you don’t even have to go through the sales training program. It’s like it’s — I have this three-week program I put all the young people through just to teach them because sales, a lot of the skillsets are really kind of critical for lots of roles, and it’s useful for everything, right? So you kind of want everyone in your organization to at least be able to sell to some degree.

But with this guy, he was so far to the marketing side that I was, like, “Oh, you know, if you don’t even feel like doing this, don’t even bother. Just double down on the marketing, like, play your strengths here.” He ended up doing the sales training anyway, probably just because almost everyone else was doing it. But three weeks later he’s like — or a month later, I don’t know, whenever it was, I see him on the phone a little bit, and I grab him, like, “Hey, you don’t have to — I know the phone’s ringing and I know the sales team’s always going to be trying to pull you in because they’re busy. But focus on what you want to do.” And he’s like, “Well, it’s actually okay. I like this.

“I like the interactions. I like the —.” And I’m like, “Okay, do what you want to do. Jump around on these projects and see what fits.” Next thing I know, he’s always on the phone [laughs]. Three months into his time at the company he’s just fully on the sales team. And so I sat him down and had a conversation with him again and we talked about how he just feels different about these types of activities. And I’m like, “Well, this is weird. I mean, let’s just have you take the survey again because it feels like your answers are all different to me.”

And sure enough, he takes the survey again and all his answers switched. Like, on a scale of one to five, he was a five; now he’s a one. He was a one; now he’s a five on different questions.

Micalizzi: Sometimes you don’t know unless you’ve done it.

Benson: That’s exactly it.

Micalizzi: And it’s one thing to say, “I love talking on the phone.” But it’s, like, if I’m calling Christina to chat, that’s a very different conversation than I’m calling Christina to, one, get her attention; two, understand her business; and three, try to find ways that I can help her. Totally different scenarios. But you don’t know unless you’ve actually done it.

And I love that you’re — in the culture you’ve created the flexibility to actually try. I mean, to Christina’s point, in many cultures you don’t want to raise your hand because it’s a career-limiting hand raise [laughs]. And to your point that sometimes your managers don’t like when you poach from their teams and you take someone and put them where they’re better suited, they’re [unintelligible].

Benson: Yeah. Oh, they’ll gripe at me. But they know where I’m coming from, right?

I mean, they’re like, “I get it. Yeah. I liked him on my team, but I can see why you’d want him over there. I get it. I get it.” I’m taking a top-down view where I’m like — and I’m taking their career in mind, right? It’s like I know they’ve been doing this for a year or two years. There are people on my team right now that are some of my best salespeople. And one person jumping in front of my mind right now, I’m probably going to pull this person out of sales, even though they’re one of our best salespeople, because they’re really good at operations management and they’re really good at marketing.

And I suspect that, long-term, that’s going to be where they land. And so they’re going to [be] great at either thing, but I suspect that’s the direction we’re going to want this person to go in.

Micalizzi: But if it’s better for them and their career and it keeps them there, it ends up being better for you company-wise.

Benson: Ends up being better company-wise. And because we do this with everyone, and they — and everyone, they’ve all heard me give this spiel 10,000 times, right [laughs]? Like they know what — they understand the philosophy. And it is hard on the organization to be moving people around and doing this.

But at the same time, from a long-term investment in the employee’s perspective, it really enriches their career.

Arroyo: And it sounds like more than just that you’ve encouraged this culture of trust. You also encouraged a culture of being okay to fail.

Benson: You have to be able to take risks. And you have to — people have to be able to fail or else they won’t take risks. You see this all the time in bigger companies. I call it the — and I don’t mean this to offend, but I call it the risk-averse middle-manager syndrome, where you don’t take a risk on something, let’s just say a hire, right? Like, a risky hire.

This person didn’t go to the right kind of school or doesn’t have the right experience or didn’t have the right background or whatever it is, whatever the thing is that’s going to make people raise their eyebrows. And you see this in a lot in larger companies, I think, especially. But you see it in small companies, too, where they’re just like, people don’t want to take a risky hire because it’s got a higher probability of going bad. They’ve never done this before. Maybe they were in a slightly different industry before, and so, you’d rather go with the safer hire that really no one would ever raise an eyebrow at that hire, right?

It’s the, “Buy IBM because you never got fired for buying IBM” — the IBM employee, right? So the risk-averse middle manager doesn’t make the risky hire. But sometimes by doing that  — because so many people won’t make the risky hire, the people that are really the safe hires, it’s much harder to — there’s more competition for those people, and the good ones are harder to get, whereas — and actually the safety or risk of the hire doesn’t have anything to do with how great they’re going to perform in the role, right? A totally safe run-of-the-mill hire on paper could end up being a bad hire.

It’s more important to try to figure that out, and you’d be better off taking a risk on someone who could be truly great and has just never gotten a shot or had the wrong background, or whatever it is, right? I encourage people to take the risk if they think it’s the right thing. And, hey, if it doesn’t work out, it doesn’t work out. I’m never going to be mad at you for taking the risk — because sometimes some of our best people have been people that other people would not have hired into the role that we hired them into because they had the wrong educational background or they had the wrong experience or whatever.

But that’s been taking those risks has really worked out for us, and I think especially here in the Bay Area where it’s really hard to find great people because everybody —

Micalizzi: Everyone wants those great people [laughs].

Benson: There are so many great companies here, and some of them are very hard to compete with from a hiring perspective. So by taking risks on what — in air quotes “risky candidates” — you can end up with great people. I try to encourage that kind of risk-taking throughout the organization. People have to know that, like — every hiring manager on my team knows that I’m not going to be mad at them if they make a hire that doesn’t work out.

And I think very few middle managers really feel that way. They feel like that’s the thing they’re judged the most on, and so they want to be able to say, “I mean, anybody could have made this bad hire. I mean, look at their resume. It’s amazing,” right? [Laughs.]

Micalizzi: But if you go for the middle of the road, you’re going to get mediocre.

Benson: Right. And that’s exactly it, right? Like, so you’ve got someone with the three years of experience and they got pushed out of their last role because, you know. And they went to a great school and have the right background, three years’ experience, got pushed out of their role because they weren’t that good at it.

Or you grab someone who’s never done anything like this and didn’t have the experience or the background or the right schools or whatever, but you think they could be really awesome — you’re often better off going with that risky hire. And that’s how you hit it out of the park, I think.

Micalizzi: Right. So let me ask: You’re a CEO. So obviously, you’ve created the culture where moving around or expressing that you’re for a different role, or you think you’re better suited for a different role, that’s acceptable in your culture.

For our listeners who span from the sales manager [or] sales leader to the reps themselves, if I were a sales leader and in my organization, maybe across the whole org, it’s really not codified,  it’s not part of the culture explicitly. But I really want to start keeping an eye out for that, both in my team and are they suited for what they’re doing, or might they be better suited to support the company somewhere else, or someone, let’s say, in marketing who really has that perfect skill set and would be amazing in sales — what do you recommend for them if they don’t already have that kind of open culture feel for it?

Benson: That’s a great question. I think this has to come from the top because a middle-level sales manager is not going to be, like — it’s unlikely that they’re going to raise their hand and say, “Hey, this guy on my team seems like he’d really be a great marketer,” and vice versa. If you’re a middle-level marketing manager, you’re not going to be, like, “Yeah, this person I have doing this and this and this, and they seem to also just be amazing at connecting with the customers.

“And they might really be great at sales. And I talked to them and they seem like they might be a sales guy.” It’s hard for that to happen unless two levels above that person, there’s kind of a message coming down like, “Hey, I’m actively looking to make sure everyone’s in their right spot, truly, for their career path.” And we might play "trades" between some of these teams sometimes. And there are a lot of benefits, too. I mean, having someone with a sales background on a marketing team or someone with a marketing background on a sales team is really valuable.

I mean, they just — they bring different things to the team. And I’ve seen that happen, too. But if it doesn’t come from the top down — and the same thing with the risk-taking, right? Like upper management needs to let middle management know, “Hey, take the risk, right? If it’s a bad hire, we’ll fire them, and it’s too bad.” But it’s better to have taken the risk. It’s better to have been able to say, “I really felt as a —.” You’re a professional. If you feel like — if you feel — or how I would talk to them, someone who’s a hiring manager on the team, is like, “You’re a professional. You know your team better than anyone. If you feel like this person’s going to be the best person for this role, I don’t care what their background is, you get to pick. And you’re responsible for it. You’re responsible for the number coming off of this sales team.” Or: “You’re responsible for the leads coming out of this marketing team. If you want them and you think they’re the one that’s going to do it, take them. It’s your team.” So I think you’ve got to empower …

Micalizzi: So you’re definitely not advising going alone.


It sounds like you’re really saying that whether you’re a rep or a manager or a middle manager, you really need to be having that conversation at least one level up about how this would be a great way to make this an even better culture and ensure we’re better staffed. That’s what it sounds like.

Benson: And if you are that middle manager, you should talk to the person who would be judging you [laughs] for screwing up.


And you should say, “Hey —.” You can explain the tradeoff, right? You can be like, “Hey, I’ve got this safe candidate — right schools, right background, right experience.

Micalizzi: They check the right boxes.

Benson: “All the boxes checked. No risk here. But they’re going to hit singles all day. Candidate B, X, Y, Z boxes are missing, or two boxes, or whatever — the boxes aren’t being checked. However, they could hit homers. I just — I feel they’ve got a big swing and they could hit homers.” So I —

Arroyo: And they’re coachable.

Benson: “They’re coachable, and we can teach them things. They seem …, they’ve got the right…,” whatever it is, whatever characteristics you liked about them that you thought they had that sparkle factor.

But your manage — if you’re a middle manager, your director or a VP or whatever has to be onboard and has to understand, “Hey, this guy’s taking a risk, or this — and we are aware of the risk that’s being taken. And I’m not going to be angry if it didn’t work out.” With no risk, no reward.

Micalizzi: Definitely. So Steve, I’m going to ask you our lightning-round question: If you could take all your knowledge and experience you have today, go back to the beginning of your career, and give yourself one piece of advice, what would you tell yourself?

Benson: Wow [laughs]. Do you ask everyone this? [Laughs.]

Micalizzi: I do, actually.

Benson: Okay [laughs]. I wish that I was able to have been able to tell myself — and this is the same stuff that I tell a lot of the young people that I work with — is figure out what career path you really enjoy and that you’re really good at, and maybe you have some exceptional skills and some standout abilities in, and figure out what those jobs are, and do that thing.

Because I was 28 in post business school before I even got into sales. And that was kind of the career path that took me to where I am today. And it was — it was actually — frankly, it was a really good friend of mine in business school who — we were practicing consulting interviews because he had been a consultant and I was about to have a consulting interview. And he stopped me when we were doing it and he was, like, “Well, do you really think this is the right fit for you because you have really good communication skills and you really connect with people?

“And I could really just see you in a sales role.” And I was like, “A sales role. Really? That’s an interesting path for an MBA.” And he was like, “Yeah, that’s not a normal path. But for you it’s the right path.” I thought about that for a while and I actually then ended up trying out a field sales job, and that’s what I started doing right after business school, and that was the right path for me. And then I was doing that for years, and then I started a company around helping field salespeople, and etcetera, etcetera. But —

Micalizzi: That’s great. So somebody put you on the path that helps you put others on the path. I love that.

Benson: Yeah. And he’s a good — actually, that buddy just texted me earlier. He’s one of the smarter people I know [laughs].


Micalizzi: It’s great to surround yourself with smart people. I love it. So, Steve, thank you so much for joining us here in the studio. I know in your day job you’re helping these field sales reps to be more productive and to get more out of their day.

But I really appreciate your stepping [to the side] and talking to us about this topic because I think not enough leaders focus on that, on making the entire company better, not just making their numbers.

Benson: Yeah. This is one that’s super near and dear to my heart, obviously. It really gets me excited. So I’m really happy I was able to come.

Micalizzi: Awesome. Thank you.

Arroyo: Thank you.

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