The Founder’s Guide to Hiring and Leveraging a Chief of Staff

At Primary, one of the most common roles we help our early-stage portfolio companies hire for is the Chief of Staff.

It’s a critical job: often, it’s the first operations hire a company makes, and becomes the founder's de facto right hand. But while the position has gained prominence in the past five years, it’s often poorly understood.

Almost every week we sit down with a founder overwhelmed with day-to-day tasks and looking to hire someone to shoulder the logistical burden. They know they need help, but don't know what to look for or even what to call the role. This is when we educate them on Chiefs of Staff: who they are, how to find them, and how to leverage them.

All in all, our team has helped 30 founders make their first operations hire. Here’s what you need to know.

Chiefs of Staff generally fall into two categories:

1. Operational generalists: Swiss Army Knives who handle a wide range of tasks, such as internal KPI dashboards, investor relations, team offsites, and HR policies.
2. Functional specialists: They handle operations but also have deep expertise in a specific area like go-to-market, product, engineering or finance.

Regardless of focus, the CoS works closely with the CEO, often spending more than 75% of their time together. Trust is an essential component of the relationship.

Timing the hire

Knowing when to pull the trigger on a Chief of Staff hire can be tricky. Hire too early and you risk having an expensive employee twiddling their thumbs; hire too late and you'll be overwhelmed and unable to make the most of the role.

Generally, the ideal time is around the Seed or Series A stage, although this can vary. When the founder's plate starts to overflow noticeably, distracting from key priorities like fundraising, selling, and product, it’s time to hire a force multiplier extension of themselves that can tackle any problem.

Signs you’re ready for a CoS include:

• Spending significant time on tasks that could be delegated, like decks for board meetings, setting up company Notion or Trello pages, any sort of general documentation, financial modeling, or dealing with vendor and lease agreements.
• Struggling to focus on core responsibilities like fundraising, sales, and product.
• Needing support to manage increasing administrative complexity.

Don't hire until you have enough work to keep a CoS busy and engaged from day one.

Kicking off the process

Start with introspection. Take a hard look at your own strengths and weaknesses as a founder and a company. Where do you need the most help? What gaps exist in your current team?

Maybe you're a strong technical founder but struggle with financial modeling and analysis. Or maybe your team lacks go-to-market expertise. Prioritize candidates who can do what you can’t.

Keep in mind that a CoS needs to operate without extensive hand-holding. They should drive results independently and be an extension of the founder’s brain. Get this hire wrong, and it just becomes another burden, requiring more of your time than if you just did the operational work yourself.

Know where to look

Most Chiefs of Staff don't come from another CoS role; you're not usually looking for someone with direct experience. Strong candidates often leverage this type of role to transition from a world like consulting or investment banking into a startup leadership role in the future.

The best place to start is by tapping into your network and relevant communities. At Primary, our Chief of Staff Mastermind Network has hundreds of candidates actively looking for these roles. A lot of VC and startup communities also have great talent pools of Biz Ops and strategy folks looking to make the move into a CoS position.

The key is realizing that this is a community-driven role. The top candidates are usually already plugged into the startup and VC ecosystem. They're going to events, engaging online, and connecting with the right people.

As a founder, your first move should be to leverage your investors, other founders you know, and any startup groups or associations you're a part of.

The ideal candidate profile

We typically see the most success with people who spent 2-3 years in a top-tier consulting firm, investment bank or private equity shop before transitioning to a startup for a year or more.

This combination of blue chip training and startup experience is powerful. It provides a strong foundation in business fundamentals — and exposure to a range of business and financial models — while also ensuring comfort with a fast pace. (You don’t want someone who feels like a fish out of water when they move from Deloitte to a 15-person company.)

Of course, there are exceptions to every rule. We've seen Chiefs of Staff from a wide range of backgrounds excel in the role. But if you're looking for a clear archetype, that consulting/finance-to-startup progression is a great template to follow.

Mindset and behavioral traits are also important. These are typical competencies we test for:

• Proactivity and comfort with ambiguity.
• Self starter. A “get things done” mindset and can build from scratch. That might mean setting up a marketing function at a company that doesn’t have one, or setting up the pipeline of investors to pitch for Series A fundraising.
• Intellectual curiosity. A founder should be able to present them with a problem the company has never faced before, ask the CoS to research multiple good solutions, and implement the best one as fast as possible.
• Strong executive presence. They have mastered communications and can “manage up” with their founder, investors, key external stakeholders, etc.
• Highly organized with excellent attention to detail.

Beyond these core attributes, a CoS is often critical in shaping company culture. Look for candidates who are infectiously positive, build strong relationships and make folks feel included. The best ones organize team building events, shape a welcoming vibe, and ensure every employee feels valued.

Leveraging a CoS

Congratulations, you hired a Chief of Staff. Now what? Getting the most out of this hire requires granting trust and autonomy, and being as clear from the jump as possible about what you want them to do. This can change over time, but the inherent nebulousness of the role requires clear swim lanes early on.

Some specific areas where they can have an immediate impact:

• Creating decks and templates.
• Hiring for the company.
• Creating financial models.
• Handling agreements and contracts.
• KPI dashboarding across the business.
• Setting up company-wide workflow and productivity apps.
• Helping in functional areas, like business development pipelines. Chiefs of Staff can help manage the funnel, follow up with leads, and join calls. If they have a tech background, they can help with engineering and product sprints.

A good CoS ensures the trains run on time. This iteration of the role typically lasts 12 to 24 months: they come in as a catch-all, handling a bit of everything. Then, after a year or two, they transition into a more specialized role within the company. That may be a leadership position in operations, product, growth — or whatever makes sense based on their skills.

Know you’ve made the right hire

Consider the sheer amount of time you'll spend with this person. Ask yourself: Is this someone I’m glad to be in constant communication with? Someone I'm excited to show off? Do I trust I can hand things off to them and those things will get done?

The right fit is a game-changer. Having someone you can trust completely, who crushes it externally and internally, who frees you up to focus on your highest-impact work: that's when you know you've gotten it right.