Join us as an Analyst, Product Support and be the first person at Holly whose whole job is getting government HR teams unstuck. Most days you're in the queue: triaging questions, debugging the strange ones, and pulling in engineering when something is actually broken. The rest of the time you build the function that doesn't exist yet — playbooks, help docs, release notes, and usage reports that show which clients are struggling before they tell us. Based in New York, four days a week in the office, as we go from 50 to 100+ government jurisdictions.

Join us as our Chief of Staff and be the person the two co-founders hand the hardest problems to. You'll own the budget, the forecast, and the cash plan; build the board deck and investor updates; and run quarterly planning across engineering, deployment, and GTM as we go from 50 to 100+ government partners. When something big has no owner yet — the People Ops function, a fundraise, a new partnership — it lands with you first. Based in New York, with about a week a month on the West Coast where our customers are.

Join us as a Staff Software Engineer, Product and set the technical direction across the product Holly runs on. You'll own architecture that spans the data model, backend, frontend, and AI systems, then help teams turn that direction into features local governments use every day. This is a hands-on, full-stack building role in a modern TypeScript stack: React with TanStack Start and Next.js across the frontend and backend (we prefer TanStack and are moving that way), Postgres for the data model, and the pipelines that turn messy government inputs into product experiences people can rely on. AI is central to the product: you'll build agentic and LLM-powered features with the Vercel AI SDK, VoltAgent, and similar frameworks/tools. You'll make the architecture calls, set the quality bar, and move fast without breaking the things customers depend on. If you're a Staff engineer who wants to own a product domain, de-risk the hardest decisions, and raise the engineering bar through systems and people, we'd love to talk.

Join us as a Staff Software Engineer, Data & AI and own the technical direction of Holly's Data Platform. Local governments publish enormous amounts of public information salary schedules, job classifications, MOUs (Labor Union Agreements), budgets but it's scattered across thousands of websites and buried in messy formats: scanned PDFs, inconsistent HTML, spreadsheets, and everything in between. You'll set direction for Holly's data platform, from ingestion and processing pipelines to canonical datasets to semantic search and retrieval to inference APIs that product teams build on. AI is part of the infrastructure, not a layer added later. You'll establish how Holly uses models for extraction, classification, normalization, matching, and search, and how we evaluate and operate those systems in production. We're a small, fast-moving team solving a problem that shapes how millions of Americans experience their local government. If you've worked with large, high-volume data and love the challenge of taming messy real-world inputs into something people can rely on, we'd love to talk.

Join us as a Deployment Analyst and be the person who makes Holly actually work for the governments who buy it. You'll onboard and train HR teams, own our help center and learning modules, and get clients unstuck fast when they hit a wall. You'll also run hands-on consulting and analytics projects with client workforce data — and because what you deliver manually today shapes what Holly ships next, you'll work directly with our product team to turn that work into product. If you want a role where client empathy, sharp analysis, and real public-sector impact are the job - and a front-row seat to how a govtech product gets built - we'd love to meet you.

Join us as our Founding Product Manager and own new modules end-to-end as we build out Holly's core platform — from the first whiteboard session through shipped product, starting with labor relations. You'll be the connective tissue between government HR officials and our builders: talking directly to customers, turning messy real-world workflows into clear product direction, and prototyping in code with AI tools to pressure-test ideas before engineering commits. This is a zero-to-one, AI-native role for a former founder or early-stage operator who's built something from nothing and treats AI as the default way to move faster. We're a small, fast-moving team solving a problem that shapes how millions of Americans experience their local government. If you want your fingerprints on the most consequential parts of what Holly builds next — and a seat where your judgment directly sets the roadmap — we'd love to meet you.

Join our Deployment team and own the customer journey as we scale from 50 to 100+ government partners. You'll run kickoffs at city and county HR offices, mostly around the West Coast, lead hands-on training that turns skeptical public servants into confident daily users, and be the first person on our team to see what's really working — and what isn't — in the field. We're a small, fast-moving team solving a problem that shapes how millions of Americans experience their local government. If you want a role where relationships, outcomes, and real-world impact are the job — and where your observations on the ground directly shape what we build — we'd love to meet you.