As a startup grows, the founder eventually becomes the bottleneck. There are too many meetings, too many decisions, and too many direct reports. When you reach this breaking point, you often hear advice to hire a Chief of Staff. However, this title is one of the most misunderstood roles in the modern technology ecosystem.
A Chief of Staff (CoS) is a role that supports the executive leader, often handling strategic initiatives and day-to-day operations. It is a position borrowed from the military and politics, adapted for the high velocity world of venture backed companies.
The CoS acts as a force multiplier for the CEO. They do not manage a specific function like sales or engineering. Instead, they manage the priorities, information flow, and decision making processes of the executive office. They are the connective tissue between the founder’s vision and the organization’s execution.
Chief of Staff vs. Executive Assistant
#The most common mistake founders make is confusing a Chief of Staff with an Executive Assistant (EA). While both roles support the CEO, their functions are fundamentally different.
An Executive Assistant manages logistics. They handle scheduling, travel, expenses, and gatekeeping. Their goal is to optimize the CEO’s time.
A Chief of Staff manages strategy and information. They prepare briefing materials, run the OKR process, and follow up on action items from board meetings. Their goal is to optimize the CEO’s attention. While an EA ensures you show up to the meeting, a CoS ensures you are prepared to lead the meeting.
Chief of Staff vs. COO
#On the other end of the spectrum is the Chief Operating Officer (COO). The distinction here lies in authority and permanence.
A COO is a permanent executive who owns specific outcomes. They manage large teams and have statutory authority over operations. They are there to run the business.
A CoS is often a rotational role, typically held for 18 to 24 months. They usually have no direct reports. They operate with “borrowed authority” from the CEO. They are there to run the CEO. They fix broken processes and then hand them off to a permanent owner. They are generalists who plug holes in the organization until a specialist can be hired.
The Proxy and The Truth Teller
#Two specific scenarios highlight the value of a CoS. First, they act as a proxy. A CoS can sit in meetings that the CEO does not have time to attend. They can make decisions based on what they know the CEO would want. This allows the founder to effectively be in two places at once.
Second, they act as a truth teller. As a company scales, information gets filtered before it reaches the top. Middle managers hide bad news. A CoS digs for the ground truth and presents it to the founder without varnish. They ensure the CEO is not flying blind.
When to Hire
#Founders should not hire a CoS too early. If you are a team of ten, you do not need a Chief of Staff. You need a product manager or a sales rep.
This role typically becomes necessary around Series B or when the headcount crosses 50 to 100 people. This is the stage where the gap between the executive team and the individual contributors becomes wide enough that information begins to get lost in the void.