WTF is a Chief of Staff?
Issue 247: Not just for The West Wing
The first WTF Series was WTF is a product designer? Due to the positive feedback, I figured it was time to bring it back with WTF is a Chief of Staff? At first glance, the title “Chief of Staff” (CoS) sounds like something out of The West Wing. Tech has a habit of borrowing roles from the military, and the CoS title originated in 19th-century Prussia. The Chief of the General Staff was the senior officer who supported the commander by managing strategy, planning, logistics, and coordination. This allowed field commanders to focus on leadership while the Chief of Staff handled operations and information flow.
Operations is a broad function. The job is quite literally to make sure things run smoothly. In startups, the CoS role often emerges when a company is early-stage—at that awkward size where it doesn’t yet need more executives, a full ops team, or an entire executive operations org.
Roles and responsibilities
In the Marvel comics, The Punisher has a key teammate—Micro. Their dynamic mirrors that of a CEO and a Chief of Staff. Frank Castle (The Punisher) is the execution-focused leader—decisive, tactical, and always in the field. Meanwhile, Micro works behind the scenes, gathering intel, coordinating logistics, and ensuring every move is backed by strategy and precision. Micro doesn’t need the spotlight; his job is to keep things running so Frank can focus on the mission. That’s essentially what a CoS does.
Let’s break down the core areas a CoS focuses on:
Unblock and pave strategic opportunities: A great CoS anticipates what their leader needs. The relationship is a two-way dialogue—sometimes the CoS is the one telling the leader what to do based on experience and insight. They might recommend initiatives aligned with leadership priorities. If fundraising is the focus, the CoS could be taking initial meetings, handling outreach, or prepping for press interactions.
Represent the leader: The CoS often acts as a proxy or ambassador. When they speak, others should feel confident it reflects the executive’s point of view.
Drive communications and org alignment: Many Chiefs of Staff come from communications or PR backgrounds. They act as a strategic communication layer between the executive and the organization.
Take on special projects: This is often code for “figure out how to make something happen.” I once worked with a CoS whose special project was building the recruiting function from scratch—defining the team, getting budget, and hiring. Another example: running a company-wide event. The scope varies, but the throughline is trust and execution.
Attributes
We’ve covered what a CoS does, but what makes a great one?
Trusted operator
A CoS can’t be disorganized. If they’re responsible for keeping the company on track, they need to have their own house in order. They get things done—no matter the chaos. They can handle a shitshow with calm and coolness.
Versatile, strategic thinker
A strong CoS can shift gears fast. I once met one who had to find a new venue for a 200-person event the day before it happened. The plan changed, and they adapted.
Force multiplier
A CoS doesn’t just execute—they scale impact. Sometimes that means doing the work themselves until it’s ready to hand off to a team. They’re always thinking about how to extend the reach of the leader and the company.
Pathways to CoS
There’s no clear-cut path to becoming a Chief of Staff. There’s no “Associate CoS” title. In startups, the role is often filled by someone who’s ambitious, organized, and able to step into any situation and make it work. In larger companies, the path may involve progressing through a series of roles that support the company’s leadership.
It often starts with operational excellence—Producer, Executive Assistant, Recruiting, DevOps, or any enablement role. From there, you might move on to support a broader scope—an executive, a co-founder, or a business unit. Once someone has proven they can run operations and logistics, the next level is strategic responsibility. That’s when someone makes the leap into a true Chief of Staff role.
Take Behzod Sirjani, CoS at Vercel. His background in insights—qualitative and quantitative research—gives him a unique lens on customer understanding. He also invests in startups and was early at iconic companies like Facebook and Slack. That mix of strategic insight and real-world experience is exactly what makes a great CoS.
Recap
Just like the Design Engineer role that rose in the 2020s, the Chief of Staff is a crucial player for modern companies—especially in an AI-first world. The CoS is the highest-confidence proxy to the executive they support.
Hyperlinks + notes
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