The Different Chief of Staff Profiles and Ways to Leverage Them

By Jo Cheng & Rebecca Price

The Chief of Staff role is notoriously nebulous—both for candidates and founders. We’ve seen more and more interest in this role within the last five years, yet founders still ask us questions about its scope and leverage.

As the Director of Community who runs the Mastermind Network, a network with hundreds of Chiefs of Staff as well as other startup functions, and Partner who supports founders with all people/talent-related matters, we’ve helped numerous founders hire their Chiefs of Staff and have seen how various profiles can make early stage startups vastly more efficient. From pattern recognition, we generally recommend hiring for this role sooner rather than later. While we’ve previously distilled this role from the candidate’s perspective, this article will demystify this role and hiring process for founders.

What is the Chief of Staff role?

While there are many ways a Chief of Staff can support founders, they should ultimately act as a strategic force multiplier, freeing up your time and energy to focus on the big picture. You should think of your CoS as your right hand, possessing a complementary skillset to your own. They fill gaps, providing support in key areas like:

• Information gatekeeping: Filtering and prioritizing information flow, keeping you informed without being overwhelmed
• Strategic planning and execution: Partnering with you to develop, lead, and execute strategic initiatives and/or setting up initial architecture for certain departments (e.g. Ops, Finance, HR)
• Internal and external stakeholder management: Building and maintaining relationships with key stakeholders across the organization and beyond
• Priority management: Ensuring you stay focused on the most critical tasks and meetings

To give an example, Jon Payne, Chief of Staff at Lyric, highlights how his typical day as a CoS is filled with “constant context switching and assessing priorities, balancing two different approaches:

• A wide-breadth approach of knocking out quick tasks to remove business operations bottlenecks (e.g., updating the cap table in Carta, onboarding a new employee, negotiating with a new SaaS vendor, and setting up Ramp cards)
• In-depth approach of focusing on 1-2 business critical workstreams (e.g., building / updating your financial model for investors, pitching to a potential customer, and building your CRM to ensure proper pipeline coverage)”

What are the different profiles?

The Chief of Staff profile can vary in seniority and functional level of expertise—sometimes ranging from an Executive Assistant (EA) to even a Chief Operating Officer (COO). From our experience, we’ve seen most early to mid-stage startups benefit from hiring a Chief of Staff at a Manager-Director level (4-10 years of experience), as at this level, they can operate autonomously and truly act as a force multiplier.

For companies navigating a nuanced, complex or rapidly evolving industry, it could be an added bonus to hire a Chief of Staff with years of deep industry experience so they can add value at a much quicker speed–imperative for early-stage companies.

Before you hire for this role, it’s important that you understand the specific needs you’re solving for. Depending on the gaps of the organization, we often find Chiefs of Staff falling under the following profiles:

1. Strategic operational generalist: This profile boasts experience across various industries and functions, often gained through consulting or working in a cross-functional startup team. They bring strong analytical and problem-solving skills, making them ideal for founders facing a myriad of very different challenges. Visionary founders who need help with operations, process, and execution on company-building across all functions can benefit greatly from this profile.
2. Finance: Having strong financial acumen and experience in financial modeling, fundraising, and M&A can be invaluable for companies scaling rapidly or fundraising. Companies with complex financial structures and processes can especially benefit from a Chief of Staff with this background.
3. GTM: Proven expertise in marketing, sales, or business development, coupled with a deep understanding of customer acquisition, market analysis, and building sales funnels, makes this profile ideal for founders focused on scaling their go-to-market strategy. Technical founders or rapidly scaling companies could benefit from this profile.

How can I set up a CoS for success as my company scales?

The responsibilities and priorities of the CoS will naturally adapt to the company's growth stages. Examples include:

• Early-stage: Establish core processes, manage fundraising, and build strong relationships with investors
• Growth-stage: Scale operations efficiently, drive strategic initiatives, and prepare for future growth rounds
• Later-stage: Navigate complex decisions like M&A, international expansion, and IPO readiness

At early to mid-stage companies, it’s most important to set them up for success by giving them the information and ownership to establish processes, being crystal clear on what your expectations are, and communicating your ideal working relationship. Beyond being aligned and having a complementary relationship, we’d be remiss to not stress the personal and cultural element to this pairing. Ganesh Ramakrishna, Founder and CEO of Lyric, comments on how “a LOT will flow through the CoS. You want someone who can handle the asymmetrical access with grace.”

When should I hire a Chief of Staff?

We get this question a lot. We typically encourage founders to hire them early–we've yet to find a founder who regrets hiring a CoS, and in most cases they say they wish they did it sooner. Dave Wigder, founder at Ply, similarly advises to “not think it’s too early. From day one, I could see the immediate impact of the role. Don’t wait too long to find the right person, as this could lead to a last-minute scramble and settling for less.”

In essence, the Chief of Staff role is nuanced and there’s no one-size-fits-all approach. While different founders have shared what has worked for them, this is a personal decision that requires thoughtfulness and introspection.