v9 Chief of Staff, Explained (Finally)

"So… what exactly does a Chief of Staff do?"

I get this question all the time. And honestly? Before stepping into the role, I wasn’t 100% sure either. 

The Chief of Staff (CoS) role is one of those mysterious jobs that everyone has heard about, but nobody understands.

• “Wait, isn’t that just a glorified Executive Assistant?”
• “I could never be a CoS, I’m not that organized.”
• “So, you’re basically a mini-CEO?”
• “Wait… how is this different from a COO?”

After eight months in the trenches, I can tell you this: Being a Chief of Staff isn’t about fitting into a single definition—it’s about being exactly what the business needs, exactly when it needs it. And that’s what makes it such a powerful (and misunderstood) role.

The Chief of Staff is like being the co-pilot to the CEO. The CEO is the driver, focused on moving fast, making big decisions, and keeping the business alive. The Chief of Staff? We make sure the wheels don’t fall off. Some days, that means navigating. Other days, it’s keeping the leadership team aligned so they don’t argue in the backseat. And occasionally, it’s making sure the engine doesn’t catch fire.

The CoS vs. The COO: What’s the Difference?

This is one of the most common questions I get. And the answer is: it depends on the company’s size and stage.

• If you’re a company with fewer than ~75 employees, you don’t need both a CoS and a COO. At this stage, the responsibilities often overlap—both roles focus on execution, alignment, and making sure the business runs smoothly.
• The COO owns execution; the CoS enables execution. The COO is responsible for running the business, managing teams, and ensuring operational efficiency. The CoS, on the other hand, operates more as a force multiplier—they focus on alignment, strategic priorities, and making sure leadership is working on the right things.
• The CoS role flexes more. A COO has a defined scope—typically overseeing operations, finance, or a mix of functions. A CoS? Their job changes based on gaps in the company. One month, they’re driving cross-functional initiatives; the next, they’re tackling organizational challenges.
• If your CEO is highly operational, you might not need a COO—but you still need a CoS. If the CEO is deep in execution, a CoS can step in to provide leverage on strategy, communications, and leadership alignment.

The bottom line? If your business is still small, a CoS can play a hybrid role. But as the company scales, the CoS and COO become two distinct roles with different focuses.

The CoS Job: Align, Execute, and Amplify

According to the Vannin Chief of Staff Framework, if the CoS role had to be boiled down to three core functions, it would be this:

Align: Keep leadership, teams, and strategy connected.
Execute: Ensure priorities turn into action.
Amplify: Extend the leader’s reach and impact.

Alignment helps prevent miscommunication, silos, and wasted efforts. Execution ensures the company moves forward instead of getting stuck in planning mode. Amplify means enabling the CEO to focus on the highest-impact work while ensuring their priorities are carried through.

The CoS & The CEO: A Partnership, Not an Echo Chamber

If the CEO is the driver of the business, the CoS is the person making sure the wheels don’t fly off. The relationship between the CoS and CEO is everything, and it works best when their strengths complement each other.

• You’re not an order-taker. You’re not a glorified assistant managing the CEO’s to-do list. You’re also not their executive coach. You’re a partner—someone who clears the day-to-day operational chaos so the CEO can focus on fundraising and driving the business forward.
• You need to be the reality check. The best CEOs don’t need yes-men. They need someone who will tell them what they need to hear, even when it’s uncomfortable.
• Your job is to connect the dots. A CEO is in a thousand conversations but doesn’t have time to process them all. The CoS sees the bigger picture—business performance, leadership dynamics, and team morale—and makes sure nothing critical slips through the cracks.

The CoS & The Leadership Team: Influence Over Authority

One of the biggest misconceptions? That the CoS is just the CEO’s mouthpiece, barking orders at the leadership team. If you try to operate that way, you’ll fail—fast.

• Trust is everything. If the leadership team doesn’t see you as a partner, you’ll just be the “person who emails action items.” That’s not leadership. The best CoS supports leaders where they need help, instead of just enforcing alignment.
• Be a sounding board. Every leader has blind spots. Sometimes they just need someone to talk through an idea with—without judgment or politics. The CoS is that person.
• Alignment doesn’t happen by accident. Teams naturally pull in different directions. The CoS makes sure priorities stay clear, roadblocks get removed, and accountability doesn’t get lost in the shuffle.

The CoS & The Team: Shaping Culture from the Inside Out

Culture is shaped in everyday decisions, team dynamics, and how work gets done. As a bridge across teams, the CoS sees where culture thrives or breaks down in real time. A great CoS doesn’t just support culture—they shape it.

• You’re the voice of the team. Leadership doesn’t always get the full picture of how employees are really feeling. As CoS, you pick up on the undercurrents—the concerns, frustrations, and morale shifts that don’t always make it into an all-hands meeting.
• You help shape the culture. Not through company values posters, but by setting the tone in how things get done. Clarity. Communication. Accountability. These things matter.

The CoS & The Board: Managing Up & Managing Expectations

Most people don’t realize how much of a CoS’s job involves keeping board relationships running smoothly.

• You’re the bridge between strategy and execution. The CEO sets the vision, but the CoS makes sure the board stays engaged with what’s actually happening in the business.
• Business updates shouldn’t be a fire drill. Quarterly board meetings are important, but ongoing communication matters more. The best CoS ensures a regular cadence of updates—monthly, quarterly, or whenever the business hits key milestones.

The Skill Sets That Matter—And Why I Didn’t Fit the “Traditional” Mold

When people talk about Chief of Staff skills, the usual suspects come up: project management, operational excellence, being ultra-organized.

And I’ll be honest—I’m not in the top percentile of hyper-organized people. But here’s the thing: The best CoS doesn’t just check a generic skill set box. They double down on what they’re uniquely great at.

The Two Skill Buckets That Matter:

#1 Interpersonal Skill Set (Critical—You Can’t Fake This One)

At the end of the day, every business is a people business. If you can’t navigate human dynamics, no amount of operational skills will save you.

• Emotional Intelligence (EQ)
• Situational Awareness
• Conflict Management
• Social Skills & Influence
• Intuition & Judgment

#2 Technical & Business Skill Set (The “Wildcard” Strengths)

Instead of focusing on the skills I didn’t have, I leaned into the ones where I excelled—skills honed from years of P&L management across different business sizes.

• Business Acumen
• Financial Modeling
• Stakeholder Management
• Strategy Execution
• Team Leadership & Culture
• Organizational Communication

The traditional top CoS skill might be project management, but my superpower? Seeing the full business picture and making sure leadership acts on it.

The CoS Career Path: Where We Come From & Where We’re Headed

One of the most fascinating things about the Chief of Staff role? There’s no single path into it. CoS come from a wide range of backgrounds, but most fall into one of these four categories:

• Consulting (McKinsey, BCG, Bain, Deloitte, etc.):Experts in strategic thinking, problem-solving, and working closely with executives.
• Startup Operations (BizOps, RevOps, Chief of Staff to Founder, etc.): Used to wearing multiple hats, scaling processes, and making things happen fast.
• Corporate Leadership (Finance, Strategy, Legal, HR, etc.): Bring deep expertise in a specific business function and strong stakeholder management skills.
• Military / Public Sector: Highly skilled in leadership, decision-making under pressure, and managing complex operations.

Traditionally, the Chief of Staff role has been seen as an 18-24 month position—a stepping stone into a bigger leadership role. And for many, that’s still true:

• Business Leaders: Many CoS transition into General Manager (GM) roles, where they take ownership of a business unit or product line.
• Operational Leaders: Others move into VP of Operations or COO roles, where they continue to drive execution, but with formal ownership of teams and P&L.
• Founders & Start-Up Executives: Some CoS end up starting their own companies, leveraging their broad exposure to leadership, strategy, and execution.

But here’s the shift we’re seeing now: There are now “career Chiefs of Staff” who stay in the role across multiple companies.

• Some CoS love the strategic influence without the pressure of full P&L ownership.
• Others prefer staying behind the scenes, driving impact without being in the spotlight.
• Companies are recognizing that an experienced CoS can drive massive value without “needing” to become a GM or COO.

The reality? There is no “one-size-fits-all” CoS career path anymore. Some use it as a stepping stone. Others make it their specialty. Both paths are valid.

Final Thought: What I Wish I Knew at the Start

If I could go back and tell myself one thing eight months ago, it would be this:

• Trust is everything. As a CoS, you don’t lead through formal authority—you lead through relationships.
  • The CEO needs to trust you to be their reality check.
  • The leadership team needs to trust that you’re a partner, not just enforcing top-down decisions.
  • The broader team needs to trust that you’re their voice, not just leadership’s messenger.
  • And the board needs to trust that the information you provide is candid and clear.
• Without trust, you’re just another operator. With trust, you’re a force multiplier.
• This role isn’t about being the most organized person in the room—it’s about making sure the right things happen at the right time.
• You don’t need to fit a mold. You need to play to your strengths.
• The best CoS doesn’t just “get stuff done.” They make sure what gets done actually matters.