Three leadership changes you should not ignore
What this week’s leadership jumps say about the year ahead.
Hey there,
The end of the year always brings a unique energy. Big changes start happening in tech—CEOs move to new companies, senior leaders dive into AI, and founders step aside to pursue new opportunities. These shifts always make me pause and take notice.
When senior leaders start to move, it often signals a shift in the market. If many move at the same time, it points to something even bigger. As operators, we can’t just copy their actions, but we can learn from their timing, motivations, and behind-the-scenes decisions.
This week, we’ll look at three major leadership changes and what they mean for founders, operators, and anyone building teams today.
Let’s get into it.
🌐 News Shortlist
1. Alan Dye Leaves Apple for Meta
Recap: Alan Dye, who led Apple’s Human Interface Design for almost twenty years, has left to head up a new Creative Studio at Meta’s Reality Labs. He will be in charge of product design, interfaces, and visual direction for Meta’s AR and VR projects. This move comes as Apple loses senior design leaders and Meta puts more focus on hardware after struggling with its metaverse plans.
Meta has attempted this before. They spent billions on the metaverse, promised a new computing platform, and ended up adding legs to avatars. So, why does it matter that they have now hired one of Apple’s top designers?
This time, the goal is not to create a fantasy world but to improve the real one. Meta now realizes that if they want people to use AR and VR every day, the product cannot feel like a tech demo. It needs to feel well-designed, seamless, and human. Dye spent years shaping interfaces that billions use without a second thought. Meta wants that expertise.
There is a larger trend happening. Apple is losing design leaders just as Meta is actively bringing them in. When a company shifts from aiming for perfection to settling for good enough, talented people start to show where the next big ambitions are.
Now we will see if Meta has learned from its metaverse mistakes. Having a vision without execution leads nowhere. But when strong execution is paired with great design talent, it can change the market.
Advice:
If you are building products in 2026, remember not to underestimate design. The most successful companies will not be those with the most AI features, but those whose products feel intuitive and alive. People choose what feels natural over what only seems futuristic.
2. Slack CEO Denise Dresser Joins OpenAI
Recap: Denise Dresser, the CEO of Slack, is leaving to become OpenAI’s first Chief Revenue Officer. She spent fourteen years at Salesforce and Slack, leading Slack through its integration after the acquisition and launching new AI features. Now, she will focus on growing OpenAI’s enterprise business. This move shows that OpenAI is shifting from research to making money at a global scale.
This is a clear sign that OpenAI is moving away from being just a research lab and is now acting like a software company focused on earning real enterprise revenue. Hiring a current CEO shows they are serious about building a strong sales operation.
This is a smart choice. Dresser may not be a well-known CEO, but she understands how to sell to large companies, close major deals, handle procurement, and create the steady operations needed for Fortune 500 clients. These skills are essential for turning AI interest into steady revenue.
There is also a cultural shift happening. Building enterprise AI now needs leaders who know sales, pricing, onboarding, renewals, and customer success—not just researchers and engineers. By hiring someone with experience at Salesforce, OpenAI is showing that enterprise AI revenue will look more like traditional software businesses than science fiction.
Advice:
If you are working on AI, take note. The focus is shifting from research to making money. Success will not just depend on having the best models, but also on having strong sales teams, good onboarding, and great customer results. Start building these strengths now.
3. Hinge’s CEO Steps Down, and It Says a Lot About the Dating App Business
Recap: Hinge CEO Justin McLeod is stepping down to start Overtone, a new dating app focused on AI and voice features that Match Group developed within Hinge. Match is backing the project, keeping a large ownership share, and moving Hinge’s CMO into the CEO role to maintain stability. Overtone is McLeod’s attempt to make voice-based connections the next big thing in dating apps, especially as users grow tired of current options.
We discussed this recently when Bumble had layoffs and changed its strategy. Dating apps may seem stable, but they actually follow trends. They grow quickly when popular, but if interest fades, the whole business can struggle. McLeod recognizes this change is on the horizon.
This isn’t a sign of trouble. It’s a smart precaution. Founders in established markets can tell when growth is slowing. That’s why McLeod is starting something new before Hinge loses momentum. We’ve seen this approach before on other platforms where user engagement drops and AI becomes the key difference.
McLeod is betting on voice-based interaction. It’s not that people suddenly prefer voice, but text-based swiping has reached its limit. To keep growing in a tired market, you have to change the experience or risk losing more users.
Also, continuity is key here. Hinge gets a steady leader as CEO. Match keeps control of the intellectual property, data, and a share in future projects. This way, the main business stays safe while they try something new.
Advice:
If you manage a product in a mature market, take note. Don’t wait until engagement drops. Start building your next idea while your current product is still strong. Make sure your operations and leadership team are prepared so you don’t hurt your main business as you try something new.
That’s it for this week.
If there’s one thing to take from these leadership changes, it’s that nothing at the top ever stays the same. Markets change, incentives change, and talented leaders go where they believe they can make a real impact.
The same goes for your team. If you want 2026 to be a better year, start now by thinking about the roles you need, the people you trust, and the gaps you can’t afford to bring into the first quarter.
If you’d like to talk through your hiring plans or team structure for next year, just reply and we’ll schedule a time.
Until next time,
Joseph Burns
CEO & Founder, Lupa