Chief of Staff, GTM Save

📍Hybrid (Brooklyn, NY) 💼 $115,000–$135,000 + Equity

About the Opportunity

We’re hiring a Chief of Staff to join our early team and partner directly with the founders to drive growth as we scale toward product-market fit.

This role is a rare opportunity to operate at the heart of an early-stage startup that’s rethinking how local governments attract, hire, and retain public servants. You’ll lead go-to-market initiatives, own high-priority strategic projects, and act as a force multiplier across sales, operations, and special initiatives.

Holly's mission is to bring millions of Americans into public service through software that treats them with hospitality and care. We’ve built the first AI-powered platform for local government workforce design—beginning with automated job classification, salary benchmarking, and position analytics.

Live with jurisdictions representing 1% of the U.S. population (and growing almost uncomfortably fast), we're replacing expensive consultants with a modern, intelligent alternative—backed by J2 Ventures, Roble Ventures, Gaingels, and leading civic tech founders. It’s based on our founders’ experiences hiring hundreds of people into local government and building govtech products used by millions of Americans.

What You’ll Do

As Chief of Staff for GTM, you’ll:

• Drive GTM execution: Operationalize sales and growth strategies—develop lead pipelines, manage outreach cadences, prepare collateral, and drive follow-up
• Own strategic projects: Tackle zero-to-one problems across sales ops, pricing, hiring strategy, partnership development, and more
• Amplify founder capacity: Coordinate priorities, prep for key meetings, synthesize context, and maintain organizational focus on the highest-leverage work
• Engage stakeholders: Join meetings with city HR leaders, budget directors, and procurement officials; track follow-ups and ensure momentum
• Shape our growth engine: Help evolve how Holly markets, sells, and supports its platform in a space dominated by slow-moving incumbents
• Bridge product & market: Capture insights from the field and translate them into product feedback and roadmap proposals

A note: We fully recognize the irony of being “Chief of Staff” for a team that could fit in an Uber. What we mean is that you will have the opportunity to lead and drive projects with a high degree of independence with the ability to marshal resources to deliver the best work possible.

You Might Be a Fit If You...

• Have 3**–5 years** experience in consulting, business operations, GTM, or startup leadership roles. Experience delivering on innovative teams in local government can be a great path as well, especially when paired with startup or sales experience.
• Thrive in ambiguity and love figuring out the fastest, smartest path from problem to solution
• Are operationally sharp, deeply organized, and quick to turn ideas into motion
• Communicate clearly—whether writing internal docs, talking to customers, or crafting strategic pitches
• Care about government, civic tech, or mission-driven work—and want your work to improve real people’s lives
• Are hungry to learn, eager to build, and excited to one day grow into a GTM leader, founder, or operator

What You’ll Get

• Founder-level access – You’ll work side-by-side with Brendan and the leadership team on every critical decision
• Strategic exposure – Shape the go-to-market playbook and own high-leverage work across sales, ops, and fundraising
• Mission-driven momentum – Help millions of public servants enter and stay in government roles that matter
• Competitive package – $110–130K base salary, 0.25–0.5% equity, platinum health plan, and hybrid work flexibility

Our Interview Process

1. Intro call (30 min) – Chat with Brendan to explore mutual fit
2. Strategic take-home (1–2 hours) – Tackle a problem you might actually solve on the job
3. GTM deep dive (30 min) – Discuss your insights and instincts for scaling early-stage GTM
4. Live collaboration session (45–60 min) – Pair with Brendan to tackle a mock sprint
5. On-site day in Brooklyn – Meet the team, present your thinking, align on culture
6. References – Two-way checks to ensure the fit goes both ways
7. Offer – Let’s build something big

How to Apply

Send a note to [email protected] explaining why this role is exciting to you, along with your resume and any relevant work samples.

Note: This role is in-person 3–4 days/week in Brooklyn. Applicants must be authorized to work in the U.S. without sponsorship. Expect startup hours: ~50–60 hours/week, with flexibility when needed.

Our commitment to inclusion and belonging: We welcome candidates of all backgrounds and encourage folks from underrepresented groups to apply. If you need accommodations, email [email protected].