Kris Duggan has a Porsche with the wrong engine. At least, it is wrong if you believe a Porsche ought to remain entirely Porsche. His modified 1990 C2 received a General Motors LS3 V8 after a collision damaged its original engine. The result offended some purists and delighted its owner. There are several ways to judge a car. Duggan appears to have reserved a vote for the driver.
It is a useful place to begin with someone whose businesses have spent so much time measuring behavior. Badgeville applied game mechanics to participation. Betterworks made goals and progress more visible at work. Today, his advisory practice concerns the decisions that turn a promising sales conversation into an actual customer. Across those jobs, the interesting question has been what gets somebody to take the next step.
A scoreboard offers an answer, provided somebody has thought carefully about the game. Duggan’s career contains both enthusiasm for that answer and reminders of how much judgment remains outside the software.
A salesman discovers the missing instruction
Born in Sydney, Duggan grew up in Houston and Southern California, earned an MBA at the University of California, Irvine, and moved to Silicon Valley in 1999. His background was commercial. Selling software required him to find the connection between a product’s capabilities and a buyer’s willingness to change.
His career included enterprise sales at WebEx, sales leadership at Socialtext and advisory work with Palantir. Those roles put him close to an awkward feature of business software: purchasing a tool and using it are separate events. An organization can complete the procurement process with great ceremony and still struggle to get anyone to adopt the thing.
Badgeville, which he co-founded with Wedge Martin in 2010, addressed that gap. Games were good at encouraging people to return, participate and improve. Duggan and Martin explored how those techniques might serve businesses. Their early research included conversations with hundreds of executives and marketers about the behaviors they wanted to encourage.
The word gamification could make the proposition sound like a cheerful application of stickers. Duggan’s explanation was more discriminating. A sales group might respond to competition. A product team might prefer collaboration and reputation. The same mechanism could encourage one audience and irritate another.
“Different game mechanics work for different audiences.”
Kris Duggan, 2012
He also acknowledged a limit that deserves a place in any sales presentation about motivation: rewards cannot repair a bad underlying experience. A badge attached to something frustrating remains attached to something frustrating. The customer’s problem survives, now wearing a tiny hat.
In 2013, Duggan and Kate Shoup published Business Gamification For Dummies. Its subjects ranged from choosing desired behaviors to designing rewards and analyzing results. The book gave a practical form to the same interest: what people do, what encourages them, and how a business can tell whether its intervention helped.
Its contents moved from defining a business objective to choosing the actions that might advance it. There were separate discussions of customer and employee programs, followed by the work of implementation and analysis. That order matters. If the objective is vague, a company can celebrate participation without learning whether it achieved anything useful. More activity is a result a dashboard can show very neatly. Whether the activity was worth encouraging takes another conversation. A reward program needs an explanation that survives beyond the moment somebody collects the reward.
Duggan also received a Bronze Stevie in the software executive category in 2013. The recognition came during a period when he was explaining these ideas to businesses and preparing for a different application of them at Betterworks.
The goals were there. Finding them was another matter.
At Badgeville, the company’s own goals were handled with slides and shared software. Writing objectives down had not made them easy to find, update or use. A commitment could be technically public while remaining effectively buried. Every office has its archaeological sites.
Betterworks, incorporated in 2013, grew out of that frustration. Duggan co-founded it with Di Wu and Paul Reeves. The proposition was straightforward enough: help companies keep track of goals and progress across teams. Objectives and key results, or OKRs, supplied a structure for connecting an ambition with measurable evidence of movement.
In a later account of its beginnings, Duggan described a team of three working with two desks. One early objective was to understand the market by meeting 30 larger prospects. More than 80 mostly cold calls produced 37 meetings. The company used its own proposed discipline on the question of whether it should exist.
His relationship with John Doerr and Bing Gordon at Kleiner Perkins connected the startup with investors who understood both enterprise software and motivation. Doerr had long advocated OKRs. Duggan had arrived at a closely related problem through running teams and selling products. The two approaches met in a company that tried to give the method a usable everyday interface.
A nudge, with office manners
Explaining Betterworks on Australian radio, Duggan described the appeal of a shared commitment. When colleagues can see what everyone has agreed to deliver, they can encourage progress and notice when something stalls. The software included cheering and nudging, small social gestures that took less effort than a carefully composed comment.
There was a question hanging over the idea: could visibility become surveillance? Duggan argued that agreeing on a few quarterly priorities could give people more independence. A manager who already understood the commitment would have less reason to demand a daily account of every movement.
That is an argument about management as much as software. The same screen can support a useful conversation or an irritating one. A public goal acquires its meaning from what happens when a person gets stuck. The interface can make the difficulty visible; the people still have to decide how to respond.
The founder still makes the calls
For all the attention paid to product design, Duggan’s advice about selling remained personal. Early customers required the founder’s involvement. In his writing about Betterworks, he described using referrals, conferences, social networks and direct outreach. Each of the first ten customers came through a different approach. There was no single magic door.
He recommended listening to how prospects explained a demonstration back to the seller. That response could reveal whether the message had landed. He also urged founders to keep pricing understandable, charge for their work and invest early in helping customers succeed.
In a 2016 essay, he offered another test: explain the startup to your grandparents. If the explanation failed, change it. Betterworks revised its sales deck every week for its first six months. The point was to arrive at language customers understood, rather than grow attached to language the company liked.
He was similarly cautious about pursuing every available market. Large prospects could pull a young company toward special requests. International opportunities could distract it from the customers it had initially chosen to serve. Focus meant making decisions about which attractive conversations to postpone.
An uncomfortable departure
Duggan stepped down as Betterworks CEO in 2017 after a former employee filed a lawsuit alleging harassment and assault. He denied the allegations. The departure belongs in the history of a company built around improving working relationships.
A March 2018 letter issued on behalf of the board said an outside investigation had found no violation of company policies. It also said the lawsuit had been dismissed that January and that Duggan resigned from the board in March. In a January 2025 statement, Duggan reiterated his denial and said the dismissal followed an insurance payment. Those accounts describe the board’s position and his response; they do not establish a court finding on the underlying allegations.
One conversation at a time
His later work included a self-imposed challenge to provide free coaching to 100 entrepreneurs. By a 2023 interview, he had passed that number. The format was deliberately personal: one-on-one conversations, with follow-up when needed. Other founders brought problems about sales, marketing, fundraising and getting a company into the market.
Today he runs First100 Advisory, where his stated focus includes pricing, negotiation, deal strategy and reaching the executives who can authorize a purchase. It is a narrower assignment than running a whole software company. It also keeps him close to a familiar moment: somebody has expressed interest, and the next decision has yet to happen.
The person outside those conversations has other interests to attend to. His blog records spearfishing off Northern California and an enthusiasm for learning the equipment and techniques. In February 2025, he wrote about visiting the Albertina in Vienna to see Marc Chagall, noticing the artist’s recurring subjects and recognizable palette. Attention can be useful without becoming a sales metric.
He singled out Chagall’s repeated returns to village life, religion and love, even as the artist moved between places. Duggan had photographed works during the visit and felt his pictures fell short of what he had seen. For someone accustomed to making a complicated proposition legible on a screen, there is a certain charm in that admission. Sometimes the thing deserves more time than its representation.
Then there is the garage. In August 2026, he republished the earlier feature about his modified Porsche. Its history began, in the telling, with a $2,000 Porsche bought in high school and eventually reached a car whose engine violated an enthusiast’s expectation of what belonged beneath the bodywork.
The purists had their objections. Duggan had a car he enjoyed driving. After a career spent asking how to measure progress, he could still appreciate an outcome that needed very little explanation.
Keep the conversation going
Writing, conversations and the companies along the way.