The Rise of the Generalist

Why range is finally being rewarded and what it means for your career.

I used to deeply envy specialists.

People with linear career arcs, who could articulate what they did with ease. The career product managers who rose up the ranks at high-growth startups. Or the VP of Growth who started as a Performance Marketing Analyst, then became a Growth Marketing Manager, then Head of Growth.

Their path was clean. Logical. Easy to explain.

Mine wasn’t.

I could never answer the “what do you do?” question in a neat sentence and I hated that. Calling myself a generalist, a utility player, or a jack-of-all-trades felt like admitting I didn’t have any real expertise. Like I was falling behind my peers.

You’d think that breaking into venture would quell some of those doubts, but it didn’t. If anything, it made them worse.

I didn’t follow the traditional path into VC through consulting, finance, or a string of venture-backed startups. And I wasn’t a pure-play investor either.

I also spent time on the post-investment support side, helping founders with GTM, sales, and fundraising. Inside venture it was known as “platform”, which, outside of venture, no one seemed to understand.

Greaaaat. 🫠 (my fav emoji btw).

The Generalist Stigma

After enough external noise telling me to pick a lane, I started internalizing the message: specialize, go deep, or get left behind.

I was committed to finding clarity over versatility. And to some extent, it worked. I got really good at articulating the red thread of my career, making it all sound clean and intentional.

But in the process, I downplayed and ignored big parts of my background, like community building, because I thought they didn’t “fit”. Packaging myself into one, neat thing was a lot harder than I expected. 😅

I had the same conversation with myself over and over again, and it went something like: Maybe operations could be the thing. I’d always been a systems thinker and problem solver, and I was often brought in to build functions from scratch.

Maybe it was marketing. I’d led brand launches, owned GTM for new products, and loved thinking about positioning and storytelling.

Maybe it was investing. I was already doing the work sourcing, evaluating, supporting founders, so why not lean in fully?

Each time, it felt like I had to amputate a different part of myself to fit the mold. Choosing one thing meant leaving something else behind and none of the lanes ever felt like the whole story.

But Here’s What Changed: The World Did.

Over time, the world started to shift.

Startups began hiring for people who could wear five hats and learn fast. AI took over more of the repetitive, executional work, which made judgement, context, and range even more valuable.

I started seeing funds scrap the traditional Associate role and rethink what they actually needed. Jackie DiMonte, General Partner at Grid Capital, put it perfectly in an interview with PitchBook:

“Our hypothesis has completely reoriented to: we want one person who’s a Chief of Staff, capable of running experiments, launching initiatives, still helpful on the deal process, but much more oriented on how we expand our influence and impact as a firm.”

New roles started emerging at the intersections: strategy + ops, product + growth, brand + community.

Suddenly, being able to connect dots, flex across disciplines, and move between contexts wasn’t a shortcoming. People were seeking it out! The world was rewarding generalists.

Even Marc Andreessen (who I disagree with on plenty) said something recently on Technology’s Daily Show that stuck with me: in the age of AI, the winners won’t be specialists. They’ll be multidisciplinary thinkers. Cross-functional. Generalists.

Now, to be clear, specialists are still essential. When I tore my ACL three years ago, I didn’t want a generalist surgeon. When it comes to cancer research, infrastructure, public health, please, give me the specialist.

But in the general world of business and startups? Being a generalist is finally having its moment. And hopefully, its staying power too.

Advice for Fellow Generalists

If you’re a generalist, I hope you’re feeling this shift too and recognizing the power in being cross-functional and having range. Here’s what I’ve learned the hard way:

Get good at telling your story.
If your path has been winding, that’s fine, but you need to help people understand it. What's the thread that connects the roles you’ve taken? The types of problems you’re drawn to? What do people consistently rely on you for? How did each opportunity open the door for the next?

Stop apologizing for your range.
You’re probably good at a lot of things. That doesn’t mean you lack focus. Especially in early-stage environments, that’s a massive asset. The people who can jump in, learn quickly, and build momentum across functions are the ones who make everything work.

But range doesn’t mean shallow.
You still need depth — just maybe not in the traditional sense. Go deep enough in a few key areas to build trust and drive results. Let those become anchors for your story. Then use your breadth to connect the dots others miss.

Ignore the title games.
Your title won’t capture half of what you actually did. Focus on what you built, how you made things better, and the outcomes. That’s the stuff that actually matters.

The truth is, there’s no one way to build a career anymore.

You can start in one lane and end up somewhere entirely different. Over time, I’ve stopped trying to contort myself into one box. I’ve realized that what felt like a lack of focus was actually a different kind of strength.

I still work with incredible specialists. I admire them. I learn from them.

But I no longer think I need to be one.

Cheers,

OO

P.S. If you’re a generalist looking for a new role in VC Platform (or to break in), my friends over at Collide Capital are hiring their first-ever Platform Lead. Here’s why you should apply:

• You’ll be building the function from scratch, but have support from the VP of Operations and budget.

• You’ll join a fund that backs overlooked founders solving global challenges.

• And you’ll get to operate at the intersection of product, community, brand, and data, driving real value for a growing portfolio.

And if you apply, let them know Olivia from Forum Ventures sent you! 💜