Why Smart, Experienced Operators Still Feel Unplaceable in Startups

I’ve spent the last few years working in and around early-stage startups. The Chief of Staff role shows up again and again in those environments.

Sometimes it’s framed as strategy support.
Sometimes as a founder leverage.
Sometimes simply as someone making sure things don’t fall apart.

Because the role sits between functions, the people drawn to it often have a similar pattern. They’ve done many things. They think across departments. They are comfortable in ambiguity but struggle to describe themselves in one clean label.

Which is exactly the conversation that led to this post.

A few weeks ago, I spoke to an operator who felt strangely stuck despite having a strong career behind him.

The call started with a simple question.
“Where does someone like me actually go?”

What followed turned into a much more interesting discussion about how roles like Chief of Staff actually work inside startups.

Who

This call was with a second-line leader with a non-linear career path:

• Family manufacturing business
• Startup exposure at Zomato
• MBA
• Investment banking
• Back to operations
• A D2C attempt
• Now helping build a holdings-style business across multiple ventures

On paper, his experience looked impressive. In practice, he felt like he didn’t quite fit anywhere.
He isn’t junior or inexperienced. But he also isn’t one clean function. And startups still hire for functions.
That’s where the tension starts.

He reached out because roles like Chief of Staff and Founder’s Office resonated.
But he wasn’t sure whether that resonance meant direction or distraction.
Was this a real structural role or just a convenient label for people who do a bit of everything?

What he thought the problem was

He framed it as a positioning issue.

“I’ve done a lot across industries and roles, but I don’t fit cleanly into finance, marketing, or ops. Where does someone like me actually go?”

More specifically, he was looking for:

• Role clarity
• Career direction
• Confirmation that his experience wasn’t too scattered
• A way to communicate value beyond a résumé

In short, he felt “unplaceable”.

What I asked

I shifted the axis of the conversation. I asked:

• What decisions are you actually making today?
• Are you owning outcomes or influencing them?
• When something breaks, do you fix it yourself or redesign how it gets fixed?
• Where does your time really go: execution, coordination, or judgement?
• What stops moving when you step away?

These questions move the conversation from titles to function, something résumés never can.

What those answers revealed

The pattern was clear very quickly.

• He already operates like second-line leadership
• His strength is not depth in one function, but cross-functional judgement
• He is most effective in ambiguity, not clean lanes
• Founders trust him to think, not just execute
• He keeps landing in “second line” roles because that is where his leverage actually is

The frustration wasn’t about skill gaps.
It was about trying to force this kind of value into traditional career ladders.

The issue wasn’t competence. It was a structural mismatch.

The real problem

Not “What role should I take?”
But “When does a role like this even make sense?”

This is where most people misread Chief of Staff and Founder’s Office roles.

These roles exist because:

• The founder is overloaded
• Decisions require constant coordination
• Execution exists, but alignment is breaking
• Bottlenecks sit between functions, not inside them

Which is why I said the uncomfortable part out loud.

Chief of Staff is a redundant role.

Not useless, just redundant by design.

If a founder can manage coordination, approvals, and decision flow themselves, this role disappears first, especially during cost pressure.
That is not a failure of the role, that is its definition.

The reframes I gave him

Stop chasing titles
Chief of Staff is not a career destination. It is a phase role.

Understand when the role is justified
It makes sense only when:

• Team size is roughly 15 or more
• The founder is coordinating five or more direct reports
• Execution exists but alignment does not
• Decisions are slowing down due to overload

The operators who thrive here usually have:

• owned revenue or outcomes before
• comfort working without clear lanes
• the judgement to challenge founders respectfully
• the ability to translate across departments

Accept the risk without romanticising it
Founder’s Office and CoS roles are among the first questioned during cost cuts. Anyone stepping into them should know that upfront.

See the exit paths clearly
This role is a training ground, not a destination:

• Department leadership
• CoS in a larger organisation
• Or eventually, building something of your own

Outcome of the call

By the end of the call, the question had changed.

From: “How do I become a Chief of Staff?”
But: “Do I actually want a career built around ambiguity, influence, and temporary leverage?”

A much more honest question.
The answer usually reveals where someone actually belongs.

Also, one brutal truth:

The startup ecosystem quietly uses Chief of Staff as a label for people who don’t fit traditional functions but are too valuable to ignore.
Sometimes that creates incredible leverage.
And sometimes it can create permanent career ambiguity.