The best Chief of Staff roles at startups are rarely posted publicly. They're filled through networks. Underdog.io is a closed, invite-only network where founders and CEOs are introduced directly to vetted operators. One profile. No cold applications. Companies come to you.
The hidden job market
The CoS role is uniquely high-trust. Founders rarely post it publicly because the role sits so close to leadership that the hire almost always comes through a warm introduction — someone a board member vouched for, a VC recommended, or a network surfaced. If you're searching job boards for CoS roles, you're competing for the scraps.
Underdog is the warm introduction layer that most CoS candidates never had access to. You build a profile once. We put you in front of the founders who are actually hiring — before the role ever gets posted anywhere.
Who gets in
Most CoS candidates come from adjacent operator roles — not the exact title. We screen for the operator mindset, communication skills, and startup experience a great CoS requires. Here are the backgrounds that consistently produce strong CoS placements in our network.
2–5 years as a BizOps or Strategy analyst or manager at a startup. You've built the systems, run the analyses, and managed cross-functional projects. You're ready to be closer to the decision-making.
McKinsey, BCG, Bain, or equivalent — 2–4 years out. Structured thinkers who communicate well, handle ambiguity, and have the executive exposure to understand how leadership teams operate.
You've done the role before and want to do it again — at a different stage, company type, or executive. The rarest profile in the network and the most in-demand. Founders trust prior CoS experience immediately.
First or second operational hire at an early startup — Head of Ops, Strategy Lead, "General Manager of everything." You've built from scratch and know how to operate without a playbook.
Associates or analysts at venture firms who want to move to the operating side. Strong pattern recognition of what good companies look like, and direct experience working with founders.
High emotional intelligence, operational rigor, and deep trust-building skills. Military CoS experience translates exceptionally well to the startup context — founders often seek this background specifically.
How it works
Underdog isn't a job board. It's a closed network — your personal introduction engine to the founders and CEOs who are hiring for exactly this role.
Tell us your background, what you've owned, and what kind of CoS role you're looking for. Takes 60 seconds. No resume, no cover letter, no retyping your work history.
We review every profile by hand. Only the top 5% are accepted. When a founder is introduced to you, they already know you've cleared our bar — which means the first conversation starts with trust, not skepticism.
Every Monday, we introduce accepted candidates to matched companies. CEOs and founders reach out directly — salary ranges included — and you decide which conversations are worth your time.
2025 salary guide
CoS compensation varies significantly by company stage. Every Underdog intro includes the salary range — so you never waste time on a role that doesn't fit your expectations.
Sources: Glassdoor, ZipRecruiter, Ask a Chief of Staff 2026 Salary Report.
Major tech hub CoS salaries run 15–25% above national averages. NYC startup CoS roles average $136K base; SF roles average $145K+. Remote roles are typically pegged to national averages.
Early-stage CoS equity (0.25–1.0%) at a company that exits at $100M is $250K–$1M+ before dilution. The earlier you join, the more the math can work in your favor.
Base salary ranges. Equity, bonus, and total compensation vary by company and individual negotiation. All Underdog interview requests include the company's actual salary range.
Companies in the network
Every company has been reviewed and approved. No staffing firms. No agencies. Just founders and CEOs at growing startups — the kind of companies where a great CoS actually makes a difference.
Not all companies are actively hiring CoS roles at all times. We match you based on what's open when you join the network.
Every time I use Underdog.io I remember that job searching doesn't have to be terrible. Thanks for the product.
Zach B. — Senior Software Engineer, NYC
Common questions
Ready when you are
One profile. Introduced directly to the founders and CEOs who are hiring — before the role ever appears on a job board. Free for candidates. Takes 60 seconds.
Get in the network — it's free →