Hire a Chief of Staff Before You Think You're Ready

The role divides into two categories: structured work and high-priority special projects.

Structured work is the recurring operational backbone of the CEO's office — things that need to happen every week, every quarter, every year, and that shouldn't require the CEO to drive them personally every time:

• Weekly and monthly updates to the company and board
• Quarterly board package
• Facilitating and running weekly, monthly, and quarterly leadership team meetings — including creating action items and ensuring they get done
• Driving quarterly OKR planning
• Managing all-hands, quarterly company presentations, and the yearly kickoff and retrospective

Special projects are the strategic initiatives I want to drive but don't have the bandwidth to execute — redesigning our org structure, running a culture listening tour, leading executive searches. These are high-impact, time-bounded projects where having a trusted operator who thinks like me is the difference between something actually happening and it sitting on a list for six months.

Beyond those two buckets, our CoS also manages my EA, maintains the internal knowledge base for the Office of the CEO, and — critically — spends part of their tenure finding and onboarding their own replacement. More on that below.

When to hire one

I hired our CoS at 120 people. Looking back, I should have done it at 70.

The right timing depends on your growth rate. At BenchSci, we were more than doubling the team every year. At that velocity, by the time you realize you need a CoS, you're already well past the point where you needed one. The faster you're growing, the earlier you should pull the trigger.

If you're a five-person company, you probably don't need one yet. If you're pushing toward 100 people and doubling annually, you're likely already late.

Who to hire

The right CoS depends on the type of CEO you are and the specific gaps you need to fill.

For me, the profile was someone creative, people-centric, capable of tackling any problem regardless of prior domain knowledge, skilled at change management, and with a background in DEI and culture. The candidates who fit that profile best tended to have an MBA and a consulting background — specifically, business design consulting.

Two things matter above everything else.

First, trust. Your CoS will be in the room for your most sensitive conversations and will represent you when you're not there. Hire someone you trust completely — ideally someone you already know.

Second, they need to understand the role is time-limited. This was advice from one of our investors, and it's right. A CoS role doesn't have a traditional career path inside most companies, which limits growth over time. We cap the tenure at three years. After that, the CoS either transitions into a senior leadership role at BenchSci or moves to a leadership position elsewhere — with our full support. Their final responsibility in the role: recruiting and onboarding their successor.

Most CEOs discover they needed a Chief of Staff about six months after they actually needed one. By then, you've already paid the cost — in slow decisions, dropped projects, and your own attention spread too thin.

Hire earlier than feels necessary. You'll know within a month whether it was the right call. We did.