How to Design a Sales Contest That Works

Effective sales competitions have these five elements.

Written by Brian Nordli
Published on Feb. 03, 2021
How to Design a Sales Contest That Works

Salespeople have long been compared to elite athletes due to their near-universal love of competition. And just like athletics, sales has become an increasingly metrics-driven profession. So, it seemed only natural to Thomas Casale that sales should have its own fantasy sports league.

Casale launched DraftSales in 2019 to make his version of fantasy for sales a reality. His platform lets managers design any number of sales competitions, from a head-to-head bracket to a team-based fantasy sales league.

“We’re getting tracked on so many different metrics that you’re competing with other people anyway.”

Users set up a point system in which every sales metric — like cold calls made, meetings scheduled or deals closed — is assigned a value. This allows salespeople across positions to pair up on teams and compete. The match-ups are then updated live, giving reps the motivation to work harder and the satisfaction of passing a colleague, Casale said.

“We’re getting tracked on so many different metrics that you’re competing with other people anyway,” he added. “So it was like: ‘Why are we only focused on getting the meeting? I want to be motivated to make more dials [too].’”

Fantasy sports has become a popular contest framework for sales teams in recent years, and DraftSales is not the only company to launch a fantasy-sales platform. The reason for that goes beyond fantasy-sports’ rise in popularity, and into the framework of the game itself. It encourages reps to collaborate, opens the door for team-based wins and has clear rules around what’s required to win.

And when a contest is thoughtfully constructed, it can create an inclusive sales environment and tap into the natural competitiveness of salespeople.

5 Keys to an Effective Sales Contest

  • Design a contest in which everyone can win — or at least qualify for the prize. This keeps everyone engaged throughout the competition.
  • Send out frequent contest updates and provide actionable insights for each rep. 
  • Celebrate when a rep qualifies for a reward. Ring a bell or send out a Slack notification to let the winners know their achievement is valued. 
  • Select a prize that will motivate the team. Talk to each rep about what’s important to them and build the prize around that feedback.  
  • Get creative with your rewards. Sometimes something as simple as a half-day off is enough to motivate a sales team to compete.


Design a Contest That Everyone Can Win

Susan Enns has won almost every sales contest she’s participated in during her career. While that might seem like a dream to some reps, she found that winning wasn’t all it’s stacked up to be.

Of course, she enjoyed the lunches with the company president, the golf trips and the hockey tickets, but the problem was there was only one winner. As the company’s clear top performer, she always took a lead no one could catch.

“Although you think that it would be extremely motivating to be the only winner, it wasn’t,” Enns said. “And I say that as a winner.”

Enns now runs a sales training firm called B2B Sales Connections, where she frequently helps sales managers design contests. Her first recommendation is always to create a contest that everyone has the opportunity to win — or at least one in which a team of employees can win.

This can be done in a couple of ways that don’t lower the bar for winning. Sales managers can run a contest based on quota attainment so that any rep who reaches 110 percent of their quota will win. Or, managers can incorporate a team-based outcome, so if each team member reaches their benchmark, there is an extra prize.

“If you can create a contest where you set the bar so that everybody can win, that’s when the real magic happens.”

When everyone can win, reps are more likely to collaborate with each other. Enns has watched senior reps run call blitzes with junior reps, high performers seek out struggling colleagues and teams overshoot revenue expectations.

“If you can create a contest where you set the bar so that everybody can win, that’s when the real magic happens,” Enns said.

Competitions should always be designed around specific behaviors the sales manager wants to drive, Casale added. However, it’s important to remember that competitions around top-of-the-funnel activities like cold calling should last for only a week or two. Otherwise, they can lead to burnout.

Beyond reinforcing sales activity, contests in which sales reps on different teams — like SDRs and AEs — compete together can also be a great way to build camaraderie, Casale said. Within DraftSales, managers can partner AEs with SDRs and have them compete against other teams.

Finding ways to mix teams up gives employees who may have never met in person an opportunity to connect and exchange knowledge, Casale said.

“This is a fun way to get people familiar with each other,” Casale said. “They’ll know, ‘Oh yeah, we were on the same team that one month,’ and now they have a connection throughout the company that they probably wouldn’t have had otherwise.”

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DraftSales Contest Image
An example of a fantasy matchup on DraftSales. | Image: DraftSales

Provide Frequent Updates and Advice

For many sales leaders, the beginning of the year is the perfect time to launch a big sales competition. It pairs well with the rollout of new compensation plans and sales targets, and it can drum up excitement after the fourth quarter.

The excitement around the competition, however, will only last so long, Enns said. It’s up to the sales leader to be the promoter, the cheerleader and the coach for the contest to really be successful.

“If you launch a sales contest and never talk about it again, it’s not going to be on anybody’s priority list,” Enns said. “But if you talk about it weekly, monthly, quarterly, and make it exciting, then it’s going to be a much more motivating contest.”

The first step in building that enthusiasm is to provide leaderboard updates at frequent intervals. There are few things more frustrating than finding out you were three deals away from winning after the competition is over, Casale said.

Seeing the results live or in an email before the competition is over can motivate a rep to make a few extra calls or work a little harder to stay on top or win. That’s why Casale made it a priority to incorporate live contest updates into DraftSales.

“If you see that it’s noon and you were passed by six people, you’re much more inclined to turn off the TV and stop browsing Facebook and get involved in the contest,” Casale said.

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In addition to leaderboard updates, Enns used to incorporate a bell that sales reps could ring whenever they qualified for the contest prize. She also sent out updates to the entire company touting the sales reps who reached their competition targets. Finding ways to recognize the winners of a contest — especially when there was more than one winner — helped increase the excitement around winning.

“If you see that it’s noon and you were passed by six people, you’re much more inclined to turn off the TV and stop browsing Facebook and get involved in the contest.”

Displaying results, however, is just the minimum a sales leader should do — like dotting the i’s and crossing the t’s, Enns said. The next level is to incorporate coaching. Whenever competition updates are distributed, leaders should calculate the daily activity each rep needs to commit to if they want to climb the leaderboard and reach the goal.

This can help struggling reps focus on what they can control, rather than dwell on their standings on the leaderboard.


DraftSales Leaderboard
An example of a DraftSales leaderboard. | Image: DraftSales

Get Creative With the Prize

Every competition needs a prize at the end. However, not all prizes are created equal. Throwing the winner a company pen may not instill much inspiration. Likewise, tickets to a baseball game could end up alienating a team member not interested in sports.

The best prizes are ones that align with what motivates the sales team, Enns said. Sales managers should take the time to ask their reps during one-on-ones about what motivates them to do their job. For some teams, it might be to fund travel and vacations. On other teams, reps might care more about having the latest technology.

“You need to know why each one of your reps is showing up every morning. You need to know why they want to work for you,” Enns said.

One year, Enns offered reps the chance to win Disney World tickets for themselves and their families for each benchmark they hit. Since most members of the team were parents, the prize was a huge hit and inspired reps to reach out and help each other meet the goal.

“You need to know why each one of your reps is showing up every morning. You need to know why they want to work for you.”

But not all competitions require a high-value prize. Pride and recognition can go a long way.

Casale often encourages sales leaders who adopt DraftSales to get creative with their rewards. Something as simple as allowing the winner to take a half day off, gifting a meal with the company president or even just promoting them on social media can be enough.

“You’re working with real professionals who are making money. Just don’t throw a pen at the winner of a sales contest that they worked hard to win,” Casale said. “We say, ‘Get creative.’”

Lately, Casale has been thinking about ways to encourage sales reps to set up their own competitions. One of DraftSales’ features lets reps create their own personal contests with each other. The platform also offers a token-based reward system that the participating company can customize. Sales reps can then challenge each other to a week of cold calling for those tokens — or for the sake of bragging rights.

Eventually, Casale hopes to create a system in which sales reps from around the country can challenge each other.

“When you give the reps the power to log on and actually win something for themselves ... it’s just more organic and powerful,” he said.

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