Match Group’s former Director of Brand Communications & Partnerships, Michael Kaye, is embarking on a new role in an entirely new industry: Director of Corporate Communications at Upstart, an AI-enabled fintech company. 

“When I began looking for my next chapter, I wasn’t chasing a title. I was chasing an opportunity,” Kaye wrote on LinkedIn.  The opportunity he found isn’t in the world of swipes and likes, but of personal loans and credit checks. 

Could the world of swipes and “U up?” texts be any more different than the world of credit checks and loans? It’s hard to picture Kaye in this disproportionately cold world, but he assures his LinkedIn followers that he’s more than ready for the job — and that fintech isn’t as “cold” as it sounds.

“Both dating and finances require an incredible amount of trust and vulnerability — and communications plays a critical role in earning that trust,” he explained. 

He’s right – tech isn’t entirely out of his realm of expertise, even if it is unexpected. As creator of the popular LinkedIn and Substack newsletter Blurring the Lines, Kaye has long rubbed elbows with business leaders, brand builders, and entrepreneurs. 

On LinkedIn, Kaye said his newsletter experience, as well as his experience as a contributing writer for Inc. Magazine, has given him valuable insight into a problem plaguing most major industries, from dating to fintech: Accessibility — or, a lack thereof. 

“One theme that comes up again and again is access,” he explained. 

We’ve seen this in the dating industry, with sky-high subscription costs and million-dollar matchmakers pricing out the average consumer. One look at any major dating app or service, and you’ll notice another common theme: AI as a proposed solution to this growing accessibility problem. 

From Match Group-owned Tinder and Hinge to other apps like Bumble and Grindr, executives increasingly use AI to help consumers save time on profiles, align their needs with matches, and make safer connections. In other words, AI has become a go-to way to signal value to consumers. 

And Kaye, too, sees AI as a potential solution to accessibility issues. “Upstart is using AI to expand access to credit,” he said. “I believe there’s an important story to tell about how technology can responsibly create greater opportunity.”

While Kaye eyes AI innovation, other industry execs are looking elsewhere for engagement solutions. 

Former Tinder CEO Faye Iosotaluno, who stepped down in 2025, is now President and COO of Entangled Publishing, a romance publishing company. And Justin McLeod, founder and CEO of Hinge, recently announced that he’s leaving the app to focus on his new offline dating company, Overtone. 

Whether AI really will transform any industry remains to be seen. But Kaye’s confidence in AI, as well as execs’ post-dating industry careers, illustrates the deepening divide between those who believe in AI’s power and those who aren’t yet convinced. 

Going forward, this chasm is likely to widen, particularly in the dating industry, as swiping fatigue pushes people — including industry leaders — both toward and away from technological solutions to deeply human problems.