Goodbye to the grind: How 5 Chicago tech sales teams hit their goals while having fun

by Michael Hines
June 19, 2019

When it comes to motivating sales teams, let’s just say “coffee's for closers” hasn’t cut it for quite some time now. Today’s sales teams mix performance-related bonuses with frequent celebrations of success and opportunities for professional development to ensure that team members are able to hit their goals and have a little fun in the process.

We reached out to five Chicago tech companies to learn how their sales leaders keep their crews motivated and focused along with how they celebrate larger milestones and achievements.

 

Showpad Chicago sales jobs

Showpad’s sales team makes celebrating success a priority. Director of Sales Katie Cantwell said these celebrations include everything from raucous (her word) dinners and nights out to photoshopping the faces of team members onto unicorns. Yes, unicorns. It’ll all make sense in a second.

 

We all know the sales job can sometimes feel like a grind. Do you have any special traditions that help your team stay motivated and focused?

On my team, we try to have some fun at work to break up the pressure and grind of sales. We start every morning with coffee together and share our goals for the day. Sometimes our goals are professional — build an account plan for my top account — and sometimes they are personal — work out after work, leg day! — but we try to keep them measurable and actionable. You can occasionally find us in a conference room playing an extremely cut-throat version of UNO.

We start every morning with coffee together and share our goals for the day.”

 

For larger milestones — think quarterly or yearly targets — how do you make sure success is recognized and incentivized?

You have to stop and celebrate the successes. After a successful quarter, we love to enjoy a raucous dinner and night out. We also have a tradition of photoshopping the faces of our top performers onto rainbow unicorns to celebrate their magical success during our quarterly business reviews. These business reviews are a time for us to reflect on our success and goals and also share best practices and hone micro-skills. On a quarterly basis, we recognize those who attain their quota in a more traditional way with personalized gifts like etched Yeti tumblers or personalized Moleskine notebooks.

 

Upwork Chicago tech sales jobs

Continuous learning and knowledge sharing play a big role on the Upwork sales team. According to Senior Director of Enterprise Sales Samantha DeStefano, part of the way the company celebrates individuals who achieve quarterly milestones is by having them present to the team so that everyone can learn from their success.

 

We all know the sales job can sometimes feel like a grind. Do you have any special traditions that help your team stay motivated and focused?

We strive to create a fun environment that is collaborative and offers opportunities for self development. We kick off the week with a Monday morning team huddle where we share personal and professional goals and strategies for the week. We motivate each other and share successes and learnings, all while making sure we hold each other accountable. At the close of every week we host a “peers and beers” session where the team shares what went well and what they learned.

On a monthly basis we get together for an all-team huddle, which includes a reminder of our team targets and goals and also provides an opportunity to recognize our colleagues. In addition, we provide wellness activities in the office, as well as ongoing peer learning and development opportunities. These come in the form of sales-led teaching sessions, trainings, fireside chats, networking events and other meetups hosted by a variety of employee resource groups.

We strive to create a fun environment that is collaborative and offers opportunities for self development.”

 

For larger milestones — think quarterly or yearly targets — how do you make sure success is recognized and incentivized?

On a monthly and quarterly basis, we recognize account executives who have accomplished a milestone within their business, seen success executing on a specific strategy or who’ve demonstrated one of our enterprise core values. These individuals are given the floor to present to the team so that we are all constantly learning with, and from, each other.

On the enterprise large account team, we run a quarterly sales contest that we’ve dubbed “Winner’s Circle.” The top producers are rewarded with an experience to enjoy alongside their winning peers and leadership. These Winner’s Circle outings are a time for us to recognize hard work and results. Experiences have included team bonding events, trivia nights, dinners and sporting events. Annually, we celebrate and recognize all sales and success members who achieved quota with an expenses-paid rewards trip. We kicked off our very first rewards trip last year.

 

Chowly Chicago sales jobs

Fact: People want to spend time outside during summer. Chowly’s VP of Sales Tom Lawton knows this, which is why he implemented a perk that allows high-performing sales team members to start their weekend early.

 

We all know the sales job can sometimes feel like a grind. Do you have any special traditions that help your team stay motivated and focused?

We strive to ensure our team is always growing, having fun and staying motivated! We have a daily meeting where we review activity and wins and preview what each team member’s plans and goals are for the day. Each meeting ends with managers asking, “How can I support you today?” Mid-day team check-ins go over daily quotas, keep the energy up and empower sales reps to give feedback and work together to hit goals as a team. We also can’t forget hitting the gong when closing a deal and seeing your achievements on TVs around the office!

One of the most admired perks of working at Chowly is something I implemented when I joined the company. If you’re pacing at 150 percent of your monthly quota by the end of day Thursday, you get a half day on Friday and can work from home. Sales may feel a little empty on Fridays, especially in the summer, but they’ve earned it!

We take great pride in rewarding those who execute, win and support others on the team.”

For larger milestones — think quarterly or yearly targets — how do you make sure success is recognized and incentivized?

From a long-term standpoint, we reward outstanding quarterly performers with awards, trophies and by recognizing them in front of their peers during kick-off meetings. Not to mention, the account executive of the quarter is presented with additional stock options. All of our managers and directors have been promoted from within so far. We take great pride in rewarding those who execute, win and support others on the team.

 

Spark Hire Chicago tech sales jobs

When it comes to celebrating success, Spark Hire takes a balanced approach. Director of Sales Brian McGarry ensures his team takes time to regularly celebrate those who are killing it in the culture department. On the flip side, he’s also exploring ways to ensure the year’s top performers are rewarded in a way that matches their contributions to the company.

 

We all know the sales job can sometimes feel like a grind. Do you have any special traditions that help your team stay motivated and focused?

There are already so many visual assessments and health indicators baked into a solid sales process that gauging performance is never murky water to navigate. A great deal of our daily, weekly and monthly focus in sales is based around these quantitative measurements, making it easy to lose sight of qualitative initiatives. Last month, we started a new tradition on our team, “Team Bomb Cyclone.” We (literally) created an award — based on Slack emojis — highlighting the individual contributor who best exemplifies our core values, irrespective of revenue generation. What’s cool for the team is that the monthly award winner is selected by a group of their peers.

We (literally) created an award — based on Slack emojis — highlighting the individual contributor who best exemplifies our core values, irrespective of revenue generation.”

 

For larger milestones — think quarterly or yearly targets — how do you make sure success is recognized and incentivized?

As a high-growth company, we’re achieving new milestones each month. Ensuring those achievements are pushing us to surpass our annual revenue goals is paramount. As a smaller team, it’s very clear to see the individual contributors responsible for those gains. While we do a terrific job of highlighting these folks monthly, we’re actively evaluating options to install a president’s club-style trip for annual revenue attainment. The whole is definitely greater than the sum of its parts. However, it’s our position that you reward those top-performing parts with killer spiffs.

 

Built In Chicago sales jobs

Built In — hey, that name sounds familiar — is a company whose sales team loves a little friendly competition. Enterprise Account Manager Maureen Liddy said the sales team competes in quarterly competitions, with the winners celebrating their successes at team outings and, on occasion, trips to the bank.

 

We all know the sales job can sometimes feel like a grind. Do you have any special traditions that help your team stay motivated and focused?

Our sales teams, both account executives and account managers, work very closely together to celebrate both the small and big wins. Every quarter our sales team has some sort of performance-based competition. Some of our most memorable celebrations include bleacher seats at a Cubs game, a paddle boat ride on Lake Michigan and even straight cash prizes.

Some of our most memorable celebrations include bleacher seats at a Cubs game, a paddle boat ride on Lake Michigan and even straight cash prizes.”

 

For larger milestones — think, quarterly or yearly targets — how do you make sure success is recognized and incentivized?

Our teams are highly motivated to hit their quarterly and annual targets. Built In’s sales leadership approach has always been to highly reward top performers. Monetarily, they are incentivized by an annual bonus after attaining their target. Team members who hit 110 percent to their target will also be eligible for our first ever all-inclusive trip.

 

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