The Rise of the Startup Chief of Staff

Let’s talk about something I’ve been seeing everywhere lately: the sudden proliferation of the “Chief of Staff” title in startups that barely have staff! Ten people, fifteen people, sometimes fewer, and boom—there it is on LinkedIn, right under the Founder/CEO.

My first reaction, maybe like yours, is often a slight roll of the eyes. The founder’s right-hand person used to be called “Sarah” or “Dave,” maybe “Director of Getting Stuff Done,” or sometimes just “that person who magically knows where everything is and stops the building from burning down.” They didn’t need a fancy title borrowed from the West Wing or Fortune 500 C-suites.

So, the question hangs in the air: Is this just title inflation, a vanity play for fledgling companies wanting to look bigger than they are? Or is there something genuinely thoughtful happening here? Is the Chief of Staff role in an early-stage company a sign of premature bureaucracy, or is it a secret weapon?

The Ghost of Roles Past

Let’s be honest; the title carries baggage. It sounds significant, meaningful, and potentially expensive. But peel back the label, and you often find the modern incarnation of a role that’s always existed in successful startups. It’s the evolution of that indispensable early hire, the founder’s shadow, the utility player who could tackle anything thrown their way.

For decades, successful founders have relied on someone – maybe a co-founder without a specific domain, maybe an early, trusted hire – to act as their extension. This person wasn’t an executive assistant scheduling meetings (though they might have done some of that too, because, well, startup). They were the person the founder could download their brain to, who could take a half-formed idea and run with it, who could manage critical projects that didn’t neatly fit into sales, marketing, engineering, or, dare I say it, HR. They were the operational connective tissue, the strategic sounding board, and the person who handled the “important but not urgent” quadrant before it became “urgent and critical.”

Why Formalize It Now? Leverage, Leverage, Leverage.

So why the more formal title now? A few thoughts, beyond a sign of the times:

1. Speed & Complexity: The startup ecosystem moves faster than ever. Founders juggle product, selling, fundraising, hiring, culture, and market shifts at warp speed. The sheer cognitive load is immense.
2. Founder as Bottleneck: Inevitably, the founder becomes the biggest bottleneck. Their time and attention are the scarcest resources. A good CoS isn’t about adding hierarchy but buying back founder bandwidth. They act as a force multiplier.
3. Strategic Horsepower: It’s not just about offloading tasks. A strong CoS brings strategic thinking. They can own cross-functional initiatives, drive internal alignment, prep for board meetings, research new opportunities, and ensure the operational engine is humming while the founder focuses on vision, key relationships, and products. Think less “Chief of Staff” and more “Chief Leverage Officer for the Founder.”

The CoS role, when done right, moves mountains. They’re less concerned with scheduling the meeting and more concerned with ensuring the right people are in the meeting, with the right information, to make the right decision, and then following up to make sure it happens. They solve problems.

Three Signs You Might Need One

Wondering if it’s time? Here’s a simple framework:

• You spend more time coordinating work than doing work. You’re ready if you spend your day answering Slacks about where to find files instead of making decisions.
• Critical things are falling through the cracks. Missed follow-ups, dropped meetings, promises made but not kept—that’s not just busyness; it’s structural weakness.
• You have zero “give” in your system. Everything else stalls if you get sick, distracted, or pulled into fundraising. No one can catch the drop.

When two out of three happen consistently, you’re not scaling anymore—you’re juggling. And you can only juggle for so long.

What Makes a Great Chief of Staff?

A Chief of Staff is not an Executive Assistant, although they might help with your calendar if it means saving a deal. They’re not your COO (yet), although the best ones often grow into operational leadership roles over time.

The ideal Chief of Staff at a startup looks something like this:

• Context Switching Superpower: They can go from fundraising decks to customer support issues without losing the plot –and always willing to go above and beyond.
• Radar for People and Problems: They can feel when something’s off, even before you can articulate it.
• Bias for Action: They solve problems without waiting for permission.
• Strong Opinions, Lightly Held: They care deeply but don’t make it personal when decisions change.
• Ego Checked at the Door: They don’t need to be the face, the star, or the founder’s shadow. They just need to win with you.

Or to borrow a sports metaphor:
They’re not trying to be the MVP.
They’re trying to make the whole team championship-caliber.

Common Missteps to Avoid

Hiring a Chief of Staff too early—or for the wrong reasons—can backfire.

Here’s how founders sometimes get it wrong:

• Treating it like a status hire. Don’t hire one because you think it makes your startup “look bigger.” Nobody cares. And you’ll end up with resentment and redundancy.
• Hiring a clone. The temptation is to hire someone just like you. Resist. You need someone who complements your gaps, not mirrors your strengths.
• Under-defining the role. “Do everything I don’t want to do” is not a job description, and neither is “figure it out.” Be clear about priorities, outcomes, and how success will be measured—even if the work will inevitably change.
• Forgetting they’re temporary (at least in this form).

If you’re lucky, your Chief of Staff will evolve. They might become your first VP of Ops, Head of People, or Head of Special Projects.

Build for the future, not just the now.

Is It Right for You?

Hiring a Chief of Staff isn’t a silver bullet. It’s not the right move for every early-stage company. It can create more confusion than clarity without a clear understanding of the real bottlenecks or the founder’s genuine readiness to delegate.

Consider it if:

• You find yourself pulled deeper into operational weeds.
• Important work is slipping because there are not enough hours in the day.
• Alignment across your growing team feels harder to maintain.

If these challenges sound familiar, it may be time—not because hiring a Chief of Staff looks impressive, but because it is necessary.

A few reminders:

• Don’t get hung up on the title. Call them Head of Special Projects, Founder’s Associate, or VP of Making Things Happen—whatever fits your culture.
• The label matters less than the function: scaling the company’s most critical resource—you.
• Before dismissing the next “Chief of Staff” title you see at an early-stage company, pause. It might not be ego; it might be a calculated move to scale the founder and, ultimately, the business.

It’s A Matter of Trust

At its core, hiring a Chief of Staff is about trust. Trust isn’t a soft requirement—it is the foundation. Without it, the role cannot succeed. It is about transferring a piece of your leadership—choosing someone to act with your judgment when you are not in the room, carrying forward your intent when your focus must be elsewhere, and upholding the standards that define the company before the structures to enforce them fully exist.

If you’re thinking about making this move—or if you’re wrestling with whether the timing is right—I’d love to hear from you. Feel free to send me a DM on LinkedIn or email me at richard@crane.vc.