We all probably have a similar picture in our heads when we think of a sales department: rows of suit-clad professionals frantically calling customers all day while managers intermittently take them into meetings to hype them up or tear them down.
These jobs have worked their way deep into the American identity through films like the hyped-up, cutthroat environment in Wolf of Wall Street or the dull, pseudo-work popularized in The Office. But while sales jobs have remained quite similar throughout the last century, they’re changing quickly today.
While some sales fields have all but completely dried up, the ones that have stuck around have increased their networks exponentially. In the age of remote work, employees often don’t even need to come into an office. As management gets thinner and sales teams spread out, employees are increasingly stressed and burnt out. It’s hard for sales managers to get their teams to meet quotas, especially when they are all working remotely and there’s no Leonardo Dicaprio to hop onstage and yell about how they’re all going to be rich every day.
To combat worker burnout and motivate teams, many businesses create incentive programs to motivate their teams. But most incentive programs are built for in-house teams, not thousands of remote workers. Many companies consider themselves lucky if they can even get ten percent participation.
Andrew Phelps and his friends were working as UX designers when they made a one-off app based incentive program to engage sales employees at an enterprise company. What they thought was a dismal engagement rating turned out to be one of the highest their client had ever seen.
They realized they had tapped into a completely undisrupted market dying for a scalable tech solution. Three years later, the team created IncentivePilot, a SaaS platform that gamifies and automates enterprise incentive programs. Their massive success has them set to bring in $6 million in revenue this year alone and they’re still growing.
Moving Some Pixels Around Can Make a Big Difference
Andrew Phelps is from Scottsdale, Arizona and lives there today. He admits he used to want to escape his hometown, but after graduating with a bachelor’s in fine arts from the University of Arizona in 2011, he decided it was more cost-effective to stay there than the big city.
“I was freelancing as a designer and realized I could visit my friends in San Francisco every month while living for much less in Scottsdale,” he says.

Andrew chose UX as his career path because he felt it was one of the most impactful ways he could use his design skills.
“I helped a friend of a friend turn his side hustle into a full-time job overnight,” he says. “We redesigned his website and tripled his customers in the first thirty days. After about six months, he quit his day job, hired employees, and his life changed. I realized that moving some pixels around on a screen can make a big difference.”
In 2013, Andrew found his way over to work as a principal designer at a UX design studio called User10. It was here he would meet his future co-founders and career.
When 20 Percent Engagement Is a Good Thing
In 2016, Andrew’s company, User10, was hired to design an app used to reward sales reps for meeting their goals. User10 put a lot of effort into the app, but when it finally ran only about 20 percent of the sales reps participated. Andrew was mortified.
“Coming from the startup world I was disappointed by those numbers and was dreading the call with the clients,” he says. “But when I got on the phone and told them, they were over-the-moon excited. They’d never seen this level of engagement before.”
When an employee engagement rate of 20 percent could make their client smile, Andrew and his team knew they were onto something. However, the project was a one-off, and Andrew and his team didn’t work again in the space for another three years. They had a feeling the opportunity might come knocking again.
Sure enough, three years later, the enterprise company they’d helped out in 2016 was back in the User10 inbox asking for more. Andrew won’t elaborate on who the client was because they are a household name: “There were some mergers over there and after things were shaken up some folks we’d worked with came back and wanted us again,” he adds. “We were excited. There was a lot of opportunity in the space and the bar was very low.”
With a giant client banging on their doors for more, Andrew and his buddies from User10 realized they were facing the chance of a lifetime. Convinced this is where they needed to go, Andrew, another User10 Principal (and longtime friend of Andrew’s) Josh Mountain, and User10 Partner Brad Wiatr spun up a new adjacent SaaS specialized in enterprise incentive programs. They called it IncentivePilot.
What IncentivePilot Does
Here’s the market inefficiency that Andrew stumbled on: large sales companies like to use incentives to encourage sales reps to hit their targets. Unfortunately, few of them know how to do these effectively at scale. Especially for remote teams.
“Scheduling is a problem. Prize delivery is a problem. Tracking performance is a problem,” says Andrew. “We set out to solve all those problems.”
The first problem Andrew and his team handled was delivering performance-based rewards to sales reps.
“A lot of companies make ‘swag’ to reward employees,” says Andrew, “They say to their manufacturer, ‘We need 10,000 t-shirts and 5,000 mugs.’ They then get charged a ton of fees to ship all that and there’s usually logistical problems getting stuff over that cause huge delays. Once you add the logistics of delivering to 1,000 people it becomes insanely problematic.”
The problem with delayed incentives is that they significantly cut employee morale. “Using the swag reward system, it could take six to eight months if I won the prize to get it delivered,” says Andrew. “If you’re using incentives to motivate and can’t deliver, employees decide it’s a facade and lose interest. If you want them to bring the hype you need to bring it too.”
When incentive speed is almost as important as the incentive, Andrew and his team realized that the most effective and efficient way to reward employees at scale was through E-gift cards. They can be bought and sent out to thousands of employees in seconds. “We focused on reward distribution at first in 2020 and now we have the best tools in the industry for sending gift cards in bulk,” Andrew says.
The most powerful, most productive motivators at work are your experiences.
Now you’re probably thinking, “Why not just give sales reps more money as an incentive?” To this, Andrew says; “Money is what people will tell you they want, but it’s not necessarily what they really want. The most powerful, most productive motivators at work are your experiences.”
And speaking of experiences, that’s the other service IncentivePilot provides: gamifying remote sales for a better experience.
Flappy Bird For Sales
Games have been a key tool for motivating sales teams for some time now. Andrew was kind enough to tell us a bit about some of the classics.
“At the end of the quarter when you’re all behind on quota, many sales teams traditionally play games like sales battleship or bingo to get morale up,” says Andrew. “I’ll give you ‘sales bingo’ as an example; when sales teams play bingo, everyone gets a bingo board of things they have to sneak into their sales calls (something small like ‘I really hope it doesn’t rain today.’). Employees need to listen to other employees’ calls for these phrases to fill out their bingo board. The goal of a game like this is to one, have fun, and two, listen to each other’s calls to learn from one another.”
These types of games do increase morale. However, as sales teams get larger (and increasingly remote) a classic like sales bingo just doesn’t work anymore. “A small team with a game on Friday that pumps up the motivation does great,” says Andrew. “Once that gets to 1,500 people, that gets tough.”
The real key service provided by IncentivePilot is gamifying remote sales. Andrew thinks their UX background makes his team perfectly suited to the task. That and their ability to empathize with sales reps.
Designers and sales folks have a lot in common. I think there are few professions that face so many rejections.
“Designers and sales folks have a lot in common,” he says. “I think there are few professions that face so many rejections.”
To create games for remote teams, IncentivePilot applied their decade of knowledge in other design industries to create maximum engagement.
“We were looking at these poor engagement numbers and then we thought, ‘What is most engaging for people online?’ The answer of course is social media and mobile games,” says Andrew. “Then we broke it down further; ‘What do mobile games do to make things stay engaging?’ We took those principles and started making simple games for sales teams.”
One of IncentivePilot’s first gamification success stories earned IncentivePilot a 79.2 percent engagement rate from their client’s sales team. It wasn’t particularly complicated either. They created an emulation of the early mobile hit, “Flappy Bird” called Tap to Flap. Every week, sales reps would get a chance to play the game until they ran out of lives and their high scores would be posted on a leaderboard. Each time a sales rep logged in to play for less than a minute a day, they would look at the messaging that field marketing had provided getting eyeballs on the latest initiatives.
Results were astronomical. The business made $41,000 more per rep during that period than their average. The players who played more than six times earned $85,629 more than their average too.
“It’s hard to stay motivated to sell every day. Reps see games like this and get excited to sell,” says Andrew.
Getting remote sales teams excited is no simple task and the industry has noticed. Andrew doesn’t give any names but claims he has multiple Fortune 500 clients today and expected revenue of $6 million this year. Almost all of his marketing is done through word of mouth from excited sales reps bringing in eye-popping numbers every quarter. He may be changing how sales teams work in the next century.
Solving Customer Problems First
Andrew says IncentivePilot’s success comes first and foremost from putting design and customers first.
“We started by just focusing on making efficiency tools for sales like better reward distribution,” says Andrew. “Once we got started, engagement was so high using our tools that we saved field marketers 40 hours per month since businesses didn’t need to rehire reps every quarter. There are a ton of hours that go into management and design and when you save people time you save people energy. I think that helps create something sticky.”

Working as a team of three co-founders, Andrew also stresses the importance of a unified front.
“Getting alignment is super important with co-founders,” he says. “We’re very good at going back to our first principles and looking at the data and challenging each other’s ideas about the next move. I’m the most guilty of being gung ho about a new idea, just because I’m excited about it. My co-founders do a great job at bringing me back down to earth, challenging my assumptions, and making sure we don’t make a stupid next move.”
With the rapid rate of innovation today, founders may feel nervous that all the greatest ideas for startups have already been snapped up. IncentivePilot’s story proves there will always be problems to solve. Gamifying sales for teams of over 7,000 is safely a twenty-first-century problem that only has become apparent due to COVID. As industries begin to stack on each other and tech gets more complex, more problems that need solutions are created every day not less.
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