More than deals: 4 Chicago tech sales teams share how they measure success

by Michael Hines
February 13, 2019

On the surface, defining success on a sales team is simple: It’s closing a deal. In reality, though, what constitutes a success can vary by company, and even by team. We recently spoke with three Chicago tech companies to learn more about how their sales teams define success — and how they celebrate it.


Vibes Chicago sales jobs

Vibes is a mobile marketing company that helps brands connect to consumers through push notifications, SMS, messaging apps, and more. SVP of Sales and Business Development John Glennon said that when it comes to measuring success, whether or not someone is hitting their quota and how they perform in relation to their teammates doesn’t tell the whole story.


What constitutes success on your sales team?

A new sales executive can take up to 12 months to ramp, so we’ve built a range of KPIs to identify how people are doing at earlier stages in their career. We focus on engagement, enthusiasm, hunger for learning and quality of engagement with brands. Later on, we look at their leadership within the team, excellence in subject matter and for them to help others learn from their strong attributes. One of our core values is “Always Be Learning,” and this is critical in the sales role at all times.

As we don’t yet sign new brands every day, it’s important to celebrate wins in other ways. This can be a positive response from a brand you feel passionate about. We also specifically look to the competitive nature of the team to drive wins. For example, we have a regular competition where each person submits an email or elevator pitch and the winner is chosen blind and wins a gift card. We also provide wins with the team that are celebrated, such as our solution demo program. We have created five levels of platform demos and provide certificates for completion of each.

One of our core values is Always Be Learning,and this is critical in the sales role at all times.”


What are some of the best ways in which your team celebrates big wins, both individually and as a team?

The second quarter of 2018, a record quarter, was a great experience that culminated in a celebration on an architectural boat tour. I had recently moved here and we have a lot of remote salespeople on the team, so having the opportunity to get the full team together on a boat during a beautiful Chicago evening was memorable.


Braintree Chicago sales jobs

Chances are that if you’ve made a purchase recently, whether on an app, online or in a store, you’ve interacted with Braintree’s technology. The company, which is backed by PayPal, builds technology that powers payments for companies big and small. As Braintree works with companies of all sizes, Manager of Inside Sales Kevin Metz said success for his team can take many forms. Regardless, the team makes sure to celebrate all wins.


What constitutes a sales success at Braintree?

What constitutes a sales success can vary depending on the specific team, due to sales cycle length in each segment. Broadly, sales success is celebrated when a merchant begins processing payments with us. That is the stage where sales generates new revenue for the company, which of course is our goal. However, in the large enterprise segment, success may be getting a contract signed or agreement in place to process [payments] with Braintree. For the largest merchants, this is a huge victory, as the sales cycle can take upward of 12 to 18 months in some instances.

We try to celebrate victories as often as we can.”


What are some of the best ways in which your team celebrates big wins, both individually and as a team?

Larger events have ranged from team-wide dinners, cracking the code together at an escape room, rolling a few games of bocce or enjoying some laughs at Second City. We try to celebrate victories as often as we can, and that may simply mean high fives or team breakfast in the office. We also share wins in organization-wide team meetings, which allows for collaborative learnings and takeaways as well as special recognition for individual sales reps.


Infutor Chicago tech sales jobs

Infutor develops data-driven technology solutions that help companies better understand their customers to make more informed marketing decisions and mitigate risk. Director of Sales Stuart Lazarus shared how the company measures success, while Account Executive Sonny Lee gave insight into how the sales team keeps its competitive edge.


What constitutes a sales success at Infutor?

Lazarus: Sales success is measured by metrics aligned to our sales team and corporate vision, values, methods, obstacles and measures, which include pipeline generation, sales attainment, execution and operational rigor. Beyond that, it is also about having passion for knowledge in the marketplace. As a growing company, our sales team goes beyond prospecting and selling to ensure we are getting our message out about the power of consumer data and the value our products can provide in a way that resonates in the marketplace.

One of the biggest sales wins was the opening of our Chicago office.”


What are some of the best ways in which your team celebrates big wins, both individually and as a team?

Lazarus: One of the most memorable ways we celebrated individual sales success was handing out oversized “lotto-type” checks to sales reps who closed big, multi-year deals. Not only did they draw attention by the sheer physical size of the checks, but they also had large values, $20,000, attached for the winning reps.

Lee: There are always SPIFFs going on that provide both compensation and other types of awards. In my previous role as a sales development rep, I won several thousand dollars through a March Madness competition for the number of qualified opportunities I achieved. Another popular contest across all sales positions resulted in a celebration event at a Wrigleyville rooftop for a Cubs game. Last year there was a survivor pool that lasted all year long. We were partnered in teams of two, and a $25,000 pot was at stake for those who could “survive” each month by completing the contest requirements.

However, one of the biggest sales wins was the opening of our Chicago office. The success we have had has allowed us to grow the business, and having an office in the city has been great for our sales team.


Spark Hire Chicago tech jobs

Spark Hire’s video interviewing platform is used by over 5,000 companies, including Ikea, Volkswagen and USPS, to streamline the interview process. In addition to hitting goals and closing deals, Sales Development Representative Joseph Simpson said that celebrating team and individual successes is key to keeping office morale high, and it also helps new team members feel welcome.


What constitutes success on your sales team?

For the sales development team, success constitutes meeting and exceeding our team and personal goals and metrics. It’s also being able to successfully explain to a lead how and why video interviewing can help their company, and scheduling a demonstration of the platform. It feels good to see a lead become a customer and to see how our platform made their life easier. For me, success also involves being a team leader and helping out my team members. Throughout my time here, I have grown personally and professionally, and that is the greatest success of all.

It feels good to see a lead become a customer and to see how our platform made their life easier.”


What are some of the best ways in which your team celebrates big wins, both individually and as a team?

We cheer and celebrate every time we hit our target, and the announcement shows up on an office TV. For some of our bigger achievements, we give out cash prizes or gift cards when a goal is reached. Other times, peers will give a company-wide shoutout to someone who has been doing a spectacular job lately. Celebrating these team and personal achievements helps with office camaraderie.

A memorable moment for me happened just after I started at Spark Hire. I had booked my first demonstration and everyone cheered for me as the info went across our TV screens. It was nice to know that everyone supported me and cared about my personal success.

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