Dan Kessler: The Future of Engagement

Building products that people genuinely want to come back to is one of the biggest challenges facing app businesses today. Ahead of his session at Appsforum, we spoke with Dan Kessler, COO of The Mind Company about why sustainable engagement starts with product value, how gamification can encourage lasting behaviour change, and why the future of growth depends on creating experiences users choose to return to, not just clever acquisition strategies. 

Q: For those who may not know, tell us about you and what you do.

I'm the COO of The Mind Company. We build mental fitness apps: Elevate for cognitive training, Balance for meditation and sleep, and Spark, our daily microlearning app. More than 80 million people have used our products. I run the operating side of the business, so finance, marketing, planning, and org design, plus making sure the strategy we agree on shows up in what we ship.

Before this I was CFO at Garner Health and Chief Business Officer at Citizen. I got to Citizen through its acquisition of Harbor, an emergency preparedness company I founded and ran as CEO. Earlier I was at Headspace, where I helped build the enterprise and international businesses, and before that I ran operations and strategy at Hallmark Labs. I started out in entertainment law, which is a strange on-ramp to consumer apps, but it taught me how deals and P&Ls work. I live in LA with my wife and two kids.

Q: How did you find yourself in this industry? What led you to The Mind Company?

I started in entertainment law in the early 2000s, right as the internet was tearing the industry apart. Most of the people around me were trying to protect the old model. The thing doing the tearing seemed more interesting to me than another independent film deal, so I moved to Silicon Valley, got my MBA, and set out to work in venture or startups.

For a while that meant tech broadly. Headspace narrowed it. I'd been meditating for years and loved it, and I believed in what that movement was doing. Working there showed me what happens when people open a product every day and it changes how they feel.

Between the mental health work, the health tech work at Garner, and the safety work at Harbor and Citizen, I kept landing on the same conclusion: this is a big emerging market with a lot of room left to run. Most people still have no real practice around their own mental fitness. The Mind Company sits in the middle of that, and it's a portfolio rather than one app, which makes for a harder and more interesting operating job.

Q: Was there a defining moment when you realized human behavior, not just technology, was the gap?

There wasn't one lightning bolt. It was user interviews and app analytics telling me the same thing over and over: intention and desire don't produce sustained engagement.

Everybody wants six-pack abs. Almost nobody wants to do the work that gets you six-pack abs. You can hand someone perfect information, a solid plan, and real motivation, and they'll still stop on day nine because the payoff is distant and today is busy.

Once you accept that, the job changes. You stop trying to convince people and start looking for the smartest ways to trick them into behavior that's good for them. Gamification is the best tool we have. Look at what we do with Elevate, or what Duolingo does. The learning is real, and the reason you show up is the streak, the competition, the small win.

Q: At Appsforum you'll be talking on engagement. What does meaningful engagement actually look like in 2026? What are companies still getting wrong?

The measure I care about is whether someone comes back on their own and is better off for it. Time in app and sessions per day don't tell you that, and neither does a streak someone keeps out of guilt.

Practically, I watch month one and month two retention against category benchmarks, because that's where you find out if the core loop works. Renewals, because that's a paying customer voting again. And blended numbers like ARPU or LTV per download, since one number captures the whole funnel through renewal and it's harder to fool yourself with.

One number that surprises people: 47% (almost half) our paying Elevate subscribers have a run streak over 100 days. Some of that is that streaks are engaging and people are competitive. The bigger point is that it proves Elevate is a product you can do every single day. That doesn't transfer. Imagine your therapist or your telemedicine company running a streak where you lose it unless you show up daily. Before you bolt a streak onto your app because Duolingo has one, ask whether daily is the right frequency for what you actually do.

Where companies go wrong is building for the funnel instead of the product. There's a whole category of app factories running excellent ads into excellent paywalls with a thin product behind them. Those businesses can't grow on their own. They're growth engines burning money, and the moment acquisition costs move against them the whole thing stops working.

Real engagement shows up in places you didn't pay for. When we launched Spark it hit the top of the App Store on day one, mostly because Elevate and Balance users came running to try the new thing. No launch budget buys that. It came from years of shipping products people liked.

Q: What emerging technology or behavioral trend do you think will reshape user engagement over the next five years?

AI, though not in the way most decks present it. Generating content is close to free now, so novelty stops being a moat. Any app can ship infinite levels, infinite lessons, infinite variations. What stays scarce is a credible reason to come back and proof that using the thing is doing something for you.

The second shift is who owns the surface. As assistants and agents take over more of a person's daily routine, apps that are pure utility get absorbed into them. If the only reason someone opens you is to complete a task, an agent will eventually do that task without you. What survives is what people want a relationship with.

On the behavior side, people are getting more discriminating rather than spending less time on their phones. The conversation is moving from "cut screen time" to "which of this is worth it." That helps you if you can show a result, and it hurts you if your model depends on being mindlessly habit-forming.

Q: If attendees leave Appsforum remembering just one idea from your talk, what do you hope it is?

Build for engagement, not the funnel. If your product isn't worth using and sharing after someone converts, no amount of acquisition sophistication saves you.

Want an extreme test? Turn off paid acquisition and push notifications for a month and count how many people still come back. That number is your actual business.