The rise of the Ultra Generalist

It’s 7 a.m. in the morning. One of the most popular tech blogs had posted a tweet about the most recent startup shutting down after several failed attempts by the founders to crack the market and reach PMF. This was Serena’s startup, a novel idea that wanted to push the boundaries of education in emerging markets.

Just last year, the same media outlet had called her startup the next big thing in EdTech, and while news of her startup shutting down is news to every other person, Serena and her founders already began dissolving the company months ago.

Right now, she is preparing to rejoin the traditional workforce after months of running her own show, and she keeps refreshing her email, scanning through the growing pile of rejections from prospective employers who all deliver the same polite brush-off.

Much like Serena, this dilemma is relatable to a countless number of CEOs, CTOs, and co-founders who find it hard to reintegrate into the workforce, and what hurts the most is that each rejection stems from the fact that they are entrepreneurs, “something which is usually one of their proudest moments.”

Wild, isn’t it?

Ex-founders and entrepreneurs who have managed to navigate this challenge either had to tap deep into their network, pick up entry-level roles to patiently climb the ladder, or take an educational sabbatical in the form of an MBA, master’s, Ph.D, or something along those lines that allow them to reintegrate into the workforce on a softer, “edu-sabbatical” note.

A Yale School of Management study underscores how pronounced this bias can be: ex-founders are 43% less likely to receive interview callbacks than non-founders with similar experience. Ironically, those labeled “successful” founders fare even worse in some cases, as hiring managers worry they won’t adapt to corporate norms or might exit once they spot a new entrepreneurial venture.

This mismatch comes at a time when artificial intelligence (AI) is transforming the global workforce in unprecedented ways. Over the past two decades:

• Clerical and administrative jobs have shrunk due to automation.
• Routine coding tasks are increasingly handled by AI, contributing to an uptick in IT-sector unemployment.
• AI and machine learning roles, by contrast, are on track to grow by 40% by 2027, according to the World Economic Forum.

But there is hope.

There is an emerging role that is picking up popularity, a term used to define a professional who can orchestrate a mix of AI agents and humans to achieve specific objectives.

A term used to describe someone who can sit in a strategy meeting, receive their “high-level” objectives and KPIs, and run with it. An objective like “increase our product visibility by 40% in Q2” instead of “research a list of PR companies and influencers we can partner with to discuss the ‘XYZ’ product campaign.”

A term for this role is called the “Ultra Generalist.”

The age of the Ex-Founder

Ex-founders fit perfectly into this box. The same traits that once seemed to limit their prospects, i.e wearing multiple hats, dabbling in every department, pivoting strategies on a dime are rapidly becoming the most valuable.

For example, if you began as a marketing professional and became a founder, you’d eventually find yourself sucked into operations, product management, and even design or software engineering. What if you were just a techie? The moment you co-found a company, you might even get pulled into design, research, customer relations, and worse sales calls, even though all you’ve dreamed of was quietly locking yourself in a small corner room while writing code to change the world.

In an age where AI handles specialized tasks, knowing a little bit about everything suddenly has immense value. A former founder who used to wear multiple hats can excel under these conditions. Whether it’s signing off on a marketing plan generated by an AI or overseeing a product feature tested by machine learning algorithms, their role is to ensure it all serves a coherent business strategy.

This article from SmartBrief describe these “ultra-generalists” as people who “communicate, solve problems, and adapt quickly,” bridging the gap between what AI can do and what an organization actually needs. And therein lies the biggest opportunity for ex-founders: businesses increasingly need people who can manage machines, not just function alongside them.

So you might have closed the doors on your startup, laid off the last of your team, and found yourself facing more rejections than you ever encountered while pitching to VCs.

Here’s the good news:

1. Your breadth is your strength: The fact that you’ve handled operations, marketing, R&D, and hiring may feel scattershot on a résumé, but in an AI-first era, it’s a superpower.
2. Embrace your story: Instead of downplaying your founder title, re-frame it. Highlight the tangible outcomes you achieved: revenue growth, product launches, user acquisitions. Show how you connect the dots across various business functions.
3. Leverage the bias: If a company refuses to see the value in your diverse background, you might be dodging a bullet. Organizations that appreciate AI generalists are more forward-thinking, these are the companies you want to work for.
4. Think like a conductor: As AI tools become ubiquitous, your role is not to out-code or out-design the specialists, but to orchestrate. Oversee different AI tasks, interpret outputs, guide the data toward strategic outcomes, and ensure the entire ensemble aligns with broader goals.

Your journey as a founder wasn’t a dead end; it was a master class in adaptability, exactly what businesses need in a future where technology rewrites the rules every other day. The rise of AI doesn’t mean humans are not needed. It just means the highest-value work is shifting, instead of competing with AI in specialized tasks, the best professionals will be those who know how to leverage AI across multiple functions. For ex-founders and generalists, this is a golden era. The ability to think across domains, adapt quickly, and drive AI-powered execution is now more valuable than ever.

If you’re currently navigating the path from entrepreneur to workforce, there’s no better time to be alive. Why?

The future of work needs you more than you might realize.