'All I do is win': How friendly competition fuels culture at 7 Chicago tech companies

Andreas Rekdal

Learning from other members of the team is crucial to developing as a salesperson, but you also won’t make it far without a competitive streak. For sales leaders who want to help their teams move the needle, it’s important to strike a balance between fostering collaboration and tapping into your team's competitive sides with some friendly competition. We asked members of seven Chicago sales teams what that balance looks like in practice.


With its talent management software, SilkRoad helps HR teams manage each employee’s experience from the time they apply until they are offboarded before leaving. Members of the company’s sales team say friendly competition helps them learn from each other.

How do you strike a balance between competition and collaboration?

“At SilkRoad, we leverage weekly and quarterly contests for sales activities as well as weekly sales stretches between our sales development teams and enterprise teams, where they compete and collaborate on messaging and best practices,” said Mike DeVries, EVP of sales and marketing. “Ultimately, while they are competing, they are also sharing about what they’re doing and what’s working, so everyone can find greater success.”

What sets SilkRoad’s sales culture apart?

“I think competition creates a more collaborative environment,” said sales development representative Ellen Donaghy. “We get the bonding experience of friendly competition and we see how other members of the team are doing things differently. It shows us who's strong in areas where we're hoping to improve, and gives us the opportunity to lean on and learn from one another.”


A provider of digital mortgage solutions for consumers, Guaranteed Rate has built its own sales training program to keep up with demand. In recruiting for that program, the company looks for people with a competitive streak, which gets an outlet in friendly competitions about anything from sales metrics to skee ball scores at Begyle Brewing Company down the street.

How do you strike a balance between competition and collaboration?

“We have a competitive environment, but it’s also an incredibly collegiate, fun and supportive team atmosphere,” said Scott Stephen, President, Online. “Employee appreciation and collaboration is an important part of our culture — from rooftop parties to awards, bonding and giving back to our local communities. We don’t just want people to succeed at work, we want them to succeed in life.”

What sets Guaranteed Rate’s sales culture apart?

“We have an open door of collaboration and find the solution that is best for our customers,” said online sales leader Matt Kilbourne. “We turn the status quo inside out and trailblaze a path through healthy competition that forces us to be the best we can be. It’s also a very much a ‘we versus me’ approach. Of course individual achievement is important in sales, but we also place a high priority on the success of the team.”


UpRight Law provides web-based legal services for consumers. The company’s sales team likes to put on its own internal challenges on top of the goals set for them by company leaders — but that doesn’t stop members from sharing insights with their colleagues.

How do you strike a balance between competition and collaboration?

“One of our core values is to achieve as team, and the sales team demonstrates this value every day as we strive to hit and exceed a team goal each month,” said Director of Sales Lisa Nelson. “Friendly competition is a huge part of driving to this goal. We have various competitions throughout the month such as the Amazing Race and Survivor that keep things fun and exciting. At any point of the day you'll hear teammates encouraging each other, as well as some heckling, which drives a fun and competitive environment.”

What sets UpRight Law’s sales culture apart?

"We challenge each other with bets and drinks on top of whatever the team incentive is any given day,” said senior client consultant Ibie Hart. “We talk about situations and how to take on different approaches towards the call. We also help each other in our areas of growth since we all have different skills that can help the other. Ultimately we share with each other so we can learn together and get better."


LearnCore provides corporate learning solutions that help companies pass on expertise from their top performers to the rest of the team. Needless to say, the company’s own sales squad puts a big emphasis on spreading best practices as quickly as possible.

How do you strike a balance between competition and collaboration?

"All new sales reps are assigned a top performer as a mentor, which encourages collaboration from day one and pushes new reps to compete for recognition," said Pat Rodgers, VP of sales. "During our weekly sales team meeting, we always review the top Pitch IQ submissions to ensure we socialize the best practices across the team. This exercise drives competition to be the best, but it also drives collaboration and consistency across the team."

What sets LearnCore’s sales culture apart?

"DJ Khaled is a very important part of our sales team culture, because with every new client, we play ‘All I Do is Win’ throughout the office,” said Chief Revenue Officer Ryan Leavitt. “In the early days of the company, every win was crucial and it was natural to celebrate every win and generate excitement. Six years later, the tradition continues and our entire sales team and company in general is proud to be recognized when the song is played."


Smokeball’s practice management software helps small law firms streamline their operations. The company’s business development reps don’t shy away from internal competitions about making the most calls or scheduling a meeting first. But at the end of the day, they’re most enthusiastic about celebrating team-wide victories.

How do you strike a balance between competition and collaboration?

“Wins are always celebrated. I love hearing my team hit the the gong — especially when I am on a sales call and have to wait for the noise to settle before continuing,” said Senior Sales Executive Tom Magna. “We compete with each other every day, but the winners are celebrated because our job is a grind and for someone to stand out from the rest means they are deserving.”

What sets Smokeball’s sales culture apart?

“We're not pitted against each other, and collaboration is encouraged,” said business development representative Kate Mauldin. “We're far more competitive with ourselves than we are with each other. If someone is in a slump, everyone steps in to help in whatever way they can.”


ParkWhiz’s on-demand parking platform connects drivers with open spots in more than 200 cities. To foster collaboration across sales teams, incentive pay is determined by regionally specific goals, rather than how teams perform relative to each other. But the company also has an ongoing spiff rivalry, with frequent banter exchanges between its Chicago and New York teams.

How do you strike a balance between competition and collaboration?

“[ParkWhiz’s incentive compensation system] sets goals for each region based on previous months' performance and measures outcomes with easily digestible, transparent data. Because each team has its own regional goals that aren’t graded against how other teams are doing, teams are willing to share best practices and support one another,” said Todd Tucker, SVP of market development. “We constantly celebrate everyone's success publicly. Conversely, and more privately, mistakes are forgiven easily and learned from in a constructive way.”

What sets ParkWhiz’s sales culture apart?

"Our sales team culture is really unique,” said Grant Milette, regional director of market development. “Competition aside, we are all here to drive sustainable value and unparalleled support to our parking partners. Within our respective markets, each and every one of us is tasked to develop and own all aspects of the supply side of our marketplace. We are constantly communicating with one another to share best practices and help out. At the end of the day success with one market is only going to allow for more opportunity in another."


With its data-driven customer feedback software, ReviewTrackers helps businesses track their ratings and reviews across all the major review sites and understand how the customer experience can be improved. Its sales department’s rituals include morning champagne and pod-wide debriefs.

How do you strike a balance between competition and collaboration?

"The entire ReviewTrackers sales team is seated in Chicago — we made it this way so we can ensure that deals are celebrated as a team as they happen, every time (champagne included),” said VP of Sales Josh Fosburg. “We've renamed Wednesdays to be called ‘Quensdays,’ in which we have a brainstorm and questions session about what's working and not working, and how we can help each other as a team.”

What sets ReviewTrackers’ sales culture apart?

"It is important to our team to make sure that all things, big and small are celebrated,” said VP of Sales Josh Fosburg. “We try really hard to set each other up for success and ensure each member of the team is informed and feels passionate about the problems our software is trying to solve."


Images via featured companies. Responses have been edited for clarity and length.

What sets your team apart? Let us know with a tip or a tweet @BuiltInChicago

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