Founding Product Manager

Holly is the HR platform built for city and county government. We help local governments modernize how they hire, classify, and manage their workforce — work that directly shapes public services for millions of people. Our platform is live across 12 states with 60+ jurisdictions representing over 10% of the US population, including major counties like Santa Clara and Contra Costa in the Bay Area, Orange County in LA, and Snohomish County in Washington State. Demand is outpacing our team, and we're building to meet it.

Holly is a seed-stage team of 20+ operators with deep roots in public service, civic tech, and AI. We’ve raised $10M from leading investors in government technology and the future of work and have grown over 100X in the last year. We center public servants and impact in every decision and we bring that same care to how we work here at Holly.

About the Opportunity

• We're hiring Holly's Founding Product Manager as we build out Holly's core platform.

• You'll report directly to Cherie, co-founder of Holly, and own new modules end-to-end — from the first whiteboard session through shipped product. (One of the first you'll take on: our labor relations module.)
• You'll be the connective tissue between our users — government HR officials — and our builders. Your fingerprints will be on the most consequential parts of what Holly builds next.

• This role is for someone who sees the public sector as one of the most important and underserved places to build, who wants to work directly alongside the people doing that work — and who treats AI as the default way to move faster and build better.

What you'll do

Scope and architect new product modules (~60% of time).

• Turn user signal into product direction. Translate ambiguous problems into clear, actionable specs and PRDs, giving engineers and designers the user context to build from without guessing.
• Test hypotheses in code. Prototype and iterate quickly with AI build tools — Claude (Artifacts / Claude Design), Lovable, v0, Figma, Cursor — to pressure-test workflows before committing engineering time.
• Drive product velocity. Shepherd features from idea to shipped product, owning scope and sequence decisions end-to-end, and doing anything and everything to unblock teams.
• Shape what success looks like. Co-own the product metrics that define whether a feature is working - adoption, engagement, time saved - and use them to decide what to double down on or cut.

Talk to users and run research (~20% of time).

• Talk directly to our customers. Learn about how they actually solve their problems, using genuine curiosity to uncover unique insights.
• Master labor relations end to end. Work closely with customers and subject matter experts to understand costing, grievances, negotiation, MOUs backwards and forwards so you can spot where the real pain lives and which features would actually move the needle.
• Grow the team's understanding of our userbase. Build and maintain user personas that sharpen how the whole team understands government HR users - and use them to form hypotheses worth testing.

Lead how Holly uses AI for product development (~20% of time).

• Partner with engineering. Help build AI into the product from the ground up, outlining AI-powered features to solve old problems in novel ways.
• Level up how the team works. Build internal tooling, reusable skills, or interesting automations that level up the team - everything from managing personal to dos to doing QA to ideating on new features.
• Own AI quality. Write, test, and maintain the production system prompts behind Holly's AI features, and define how we measure "good" - building eval sets from real examples and iterating against them, not vibes.
• Take what works and bring it to Holly. Stay current on what's changing in AI and how product teams are using AI to move faster. Translate "what's newly possible" into tomorrow's roadmap.

Who You Are

This is an AI-native, zero-to-one product role on a small team building for government. The strongest candidates pair real product-building experience with hands-on AI fluency — people who turn AI into shipped product, not just decks — and feel the pull of the mission.

• 5-8+ years of product experience, with meaningful zero-to-one work — you've taken a product or major feature from nothing to live. You've built, not just managed a backlog.
• Founder DNA - you've built something from zero, whether it's your own company, product, or team, and know how to operate without a complete spec or a lot of structure. You create it.
• B2B enterprise, legacy SaaS, or deployment-heavy software background - you're comfortable with complex workflows, real implementations, and customers who depend on the software to do their jobs.
• Outcomes-oriented - you optimize for measurable impact and adoption, not output, and make the right tradeoffs between user needs, business priorities, and delivery constraints to get there.
• Curious and collaborative - you question things deeply, work through opinions in the open, then translate the discussion into a conclusion and ship.
• Comfortable with data - you can get into the numbers yourself to find a signal, size a problem, or check whether a feature is working.
• Drawn to the mission - demonstrated interest in public sector / social impact. Govtech or public-sector experience is a strong plus.

AI fluency — you reach for AI by default, are always testing new tools, and bring the rest of the team along.

• AI as a force-multiplier — you already use AI daily for research synthesis, data analysis, competitive teardowns, and drafting specs, and you can wire messy inputs (spreadsheets, PM tools, meeting notes) into reusable workflows that produce consistent, actionable outputs — briefs, analyses, tickets — not just summaries.
• AI-first decomposition — Given a messy government HR workflow, you can break it into what an LLM should automate, what needs a human in the loop, and where deterministic logic is safer — designing for the failure modes (hallucinations, edge cases) up front.
• You design AI for trust — public-sector HR decisions (classification, compensation, hiring) demand accuracy, transparency, auditability, and human oversight. You make AI outputs reviewable and defensible, not just impressive.
• You can use AI tools to write code — you understand code syntax, data structures, and how to prompt tools like Claude Code or Cursor effectively. You can produce production-ready code for simple UX changes yourself, and you know when to hand off more complex work to our engineering team.

What You'll Get

• Direct impact – the modules you own will be used by government HR teams serving millions of citizens.
• Shape the product team. As an early product hire, help build the team, practices, and culture as it grows — setting how product gets done at Holly.
• At the frontier of AI-native product. Build on a team that treats AI as the default, with room to work hands-on with the best tools in the market and help define what AI-native product development actually looks like.
• Competitive package. $150,000 – $185,000 USD base with equity, comprehensive health benefits (platinum plan with vision and dental), 401(k) match, and a professional development stipend.
• Collaborative work culture. Join a small, high-trust team that cares about the work and each other.

Ready to join us? A few important notes:

• Interview process:
• • Initial screen (20 min)
  • Take-home assignment (~2 hours)
  • Case interview (45-60 min)
  • Onsite at Holly HQ in NYC
• NYC-based, in-person. Our engineering, product, and deployment teams are majority based in New York City, and we work together in person. This role is based in NYC, 4-5 days a week. 
• Hours. We're an early-stage startup serving government clients with real deadlines, and many of our largest customers are on the West Coast. We care about ownership and outcomes, not clock-watching, but want to be transparent that this is a high-intensity role with long days and long hours (~60-65 a week), and the occasional fire drill around launches or critical issues. 
• Travel. 
• • Roughly quarterly to customers. Expect quarterly travel for in-person user research with government HR teams, most often in California, where many of our largest clients are based.
  • Team onsites. We bring the team together throughout the year at quarterly onsites for functional groups, and an annual company offsite.
• Applicants must be authorized to work in the U.S. without requiring sponsorship.

Holly is committed to building a diverse company and working with the broadest talent pool possible. We encourage applications from all races, religions, national origins, genders, sexual orientations, gender identities, gender expressions, and ages, as well as veterans and individuals with disabilities.