How to Build a Sales Team That Nobody Wants to Leave

Smokeball’s product might “sell itself,” but that’s not the only thing that makes life on the company’s sales team worthwhile.

Written by Adrienne Teeley
Published on Nov. 09, 2021
How to Build a Sales Team That Nobody Wants to Leave

Take a look at some of the most old-school industries, like banking, real estate and accounting, and you’ll see they aren’t so traditional anymore. With more technology companies building niche solutions and hyper-specific software, sectors that hadn’t seen change in decades are now able to tap into tailored, modern tools and move faster than ever.

That means that some unexpected market spaces, like legal tech, are now shockingly competitive, said Allison Gibson, director of sales for Smokeball. And while that should make it harder for her team to sell the company’s legal practice management software, Gibson said that’s not the case.

“Smokeball stands out because of how good the product is,” she said. “I’d never seen this kind of quality in the industry before, and that drew me to the company. I wouldn’t be good at selling something I didn’t believe in.”

“That’s the really amazing part,” Account Executive Sam Klemz said. “Smokeball’s product sells itself.”

Gibson and Klemz are likely being modest: As any seasoned rep can attest, B2B sales aren’t always easy. But that’s where Smokeball’s culture comes into play, the team said. 

“One day you might be up and the next day you might be down, so you need to rely on the people around you to help you,” Gibson said. “It’s a matter of knowing everyone has your back and you need to have theirs in the same way.”

That kind of close-knit, collaborative teamwork doesn’t happen by chance. According to Luke O’Connor, vice president of sales, it’s only one part of Smokeball’s efforts to support and retain its team for the long run. Aside from the culture, the company champions its team in concrete ways, like a generous compensation package, impressive career growth opportunities and the chance to scale with the company as it matures.

“We’re building processes not for processes’ sake, but for progress,” O’Connor said. “I think we’ll see the long-term effects of that work in the next year as we break some really big records and hit key milestones. This team is really good, and I don’t think we’re even close to reaching our full potential.”
 

How is Smokeball’s culture different from other sales teams? What stands out to you?

O’Connor: I’ve only been with the business for five months, but when I first walked in the door, the level of collaboration almost shocked me. I knew it would be good, but it’s next level: There are people co-piloting, celebrating each other’s deals and trying to push each other up the sales mountain each month. 

This isn’t a place where you can hide. I’m not even talking about results, but taking part in this team. For people who are used to huge sales teams where they don’t give much input or talk about their deals, it could be a bit of a shock. But here, we have the vulnerability to talk to each other when things aren’t going well, or if we want to improve our skills. People who come in with a willingness to learn, and have the drive to be the best they can be, are going to be successful. 

Gibson: We are competitive with ourselves as individuals, so there’s no need to add additional competition across our team. We’re close and we have these great relationships with each other because nobody knows what you’re going through professionally except the people who work alongside you all day. The more you can spend time with your colleagues and pass ideas back and forth, the more it strengthens your bond and helps you build your skill set. 


 

Employee at Smokeball plays ping pong in the office
Smokeball

 

What does collaboration look like on your team? Why is that important in sales?

Klemz: We’re not only colleagues; a lot of us are friends outside of work. We approach working together as more of a friendship. 

We have a very open level of communication at Smokeball, and someone is always available to answer any question you may have. It’s amazing because some of the more experienced reps have a lot of insight into our processes and some of our newer team members bring in ideas from their previous roles. Everyone has some kind of experience and perspective that they bring to the table. 

Gibson: A few months ago, we put some reps of different experience levels together and had them work side by side. To Sam’s point, everyone can learn something from someone — it doesn’t have to be the longest-tenured employee teaching everyone. There are things you can learn from new people because they see it all from a different perspective. We all have an understanding that we can learn from each other, which I think is so important. 

 

Your team has a core behavior that’s “check your ego at the door.” How does that play into the team dynamic?

O’Connor: If someone came in here and made everything about themselves, that person would stick out like a sore thumb. Our work is not about winning; it’s about winning the right way. We don’t cut corners or step over people, and we know it’s OK to not be correct all of the time. We bang the drum about this every day because it’s really nonnegotiable to us. 


 

Picture of interior of Smokeball's Chicago office with logo and branding on glass wall
Smokeball

 

We heard you recently refocused your compensation structure. How has that impacted the team?

O’Connor: Previously, we were targeting all of our sales reps based on how many users they sold to every month. But we thought that there might be more room to reward higher performance.

We essentially put accelerators in to guide the path of what’s possible. We shifted away from measuring users, which is still an incredibly important metric for us, but we now focus on total contract value. This enables us to play with the size of the deal, length of contract and how we discount. It rewards our team’s best performers. We want to retain our best people because we’re creating something special here. 

Klemz: I actually looked at the compensation structure this morning and realized that even once you reach your main goal, there’s always another goal for you. So, even if you’ve crushed it for the month, there’s always another reward.  

Gibson: Our commission structure has always been incredibly generous, and this recent adjustment to our comp structure sets it even higher. You can tell it’s been built by people who understand the day-to-day life of a salesperson because it motivates reps and rewards them. There’s no reason why you can’t keep pushing yourself and doing more, and then get rewarded for your extra effort. 


We can really build our career growth, while having seasoned people as our anchors to guide the process.”

 

What opportunities are there for you to grow your career at Smokeball? What has this looked like for you?

Klemz: The career growth at Smokeball is really unmatched. There’s so much opportunity here to move into another role. I started off as a business development representative and was able to move into my next role fairly quickly. As a growing business, there are new roles and opportunities being created. And lateral movement within the company is encouraged if there is a need and it is a better fit for the individual.

For me, I expressed interest in moving into an account executive role. I then started working more with the AE team to see if I might be a good fit. Some of that career growth was from having a self-starter mentality, but the managers at this company really look for where people could fit into new roles and encourage career development. 

Gibson: When leadership approached me about moving out of my sales position — which I loved — it was part of their initiative to promote from within. Who better to bring in than people who’ve done the job? 

It was great because I was given the ability to move into a leadership position, gain more experience and learn from Luke. We’ve got the foundation here so we can really build our career growth, while having seasoned people as our anchors to guide the process. 

 

Responses have been edited for length and clarity. Images via Smokeball.

Hiring Now
Origami Risk
Information Technology • Insurance • Professional Services • Software • Analytics