Deployment Strategist

Deployment Strategist

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 8 states with 35 jurisdictions representing nearly 5% of the US population, including major counties like Santa Clara, Contra Costa, Orange County, and Snohomish.

Demand is outpacing our team, and were building to meet it. Holly is a 10-person team with deep roots in public service, civic gov tech, and AI, backed by $2.2M from leading investors in government technology and the future of work, including J2 Ventures, Roble Ventures, and Gaingels. We build for the people we serve, centering public servants and impact in every decision, and we bring that same care to how we work here at Holly.

About the Opportunity

Were hiring our first Deployment Strategist as we scale from 35 to 100 government clients. Youll own the full implementation journey for new partners - cities, counties, special districts - from the moment they sign through their first months on the platform. That means running kickoff sessions at county HR offices, leading 4-6 weeks of structured training, and making sure teams are genuinely confident using the product on their own.

At full pace, youll be managing 2-3 simultaneous launches. Youll frequently be in rooms with two to twenty public servants, many of them using AI for the first time. Youre their entry point - and youll shape the outcomes they get.

This role is for someone who sees the public sector as one of the most important and underserved places to build - and wants to work directly alongside the people doing that work.

What youll do

• Launch government partners onto Holly. Own the full implementation journey from a kickoff session (often in-person at a county HR office) to structured training in the weeks that follow, to ensure the team is confidently using the platform on their own. Youll keep timelines tight and stakeholders aligned across multiple launches at once.
• Stay close after launch. Track usage, spot problems before they escalate, troubleshoot data issues, and step in when a client identifies a new use case, hits a workflow challenge, or brings on new team members who need onboarding.
• Shape the product. Observe patterns no one else on the team sees - whats confusing, whats missing, what would save a client hours. The path from customer insight to shipped feature runs through you.

Who You Are

• You understand how local government works and you know that getting people to adopt new tools is as much about relationships and trust as it is about the software.
• Youre a strong project manager who follows through. You ask good questions, stay close to the details, and dont consider a launch successful until the client is actually getting value.
• Youre energized by talking to government folks for the vast majority of your day and frequent travel for in-person collaboration up and down the West Coast and across the country as we expand.
• Youve worked in or alongside the government or in a customer-facing role where you owned outcomes end-to-end - and youre ready to bring that experience to Hollys clients.

What Youll Get

• Direct impact - because of your work, real government clients will learn to use the platform for critical projects that will improve the quality and output of the public sector.
• Playbook ownership - youre not just executing a playbook; youre writing it. What you learn shapes how Holly scales to 100 customers.
• Competitive package - $90K - $125K base with equity, comprehensive health benefits (platinum plan with vision and dental), 401k benefits, and a professional development stipend.
• Collaborative work culture - join a small, high-trust team of A players that cares about the work and each other.

Ready to join us? A few important notes:

• Interview process: Initial screen (30 min), Take-home assignment (~2 hours), Case interview (45-60 min), Onsite at Holly HQ in NYC.
• Location: California preferred or willing to travel to California up to 3 weeks/month.
• Work Philosophy: Were an early-stage startup serving government clients with real deadlines. There may be occasional off-hours work around launches or critical issues. We value flexibility and trust you to manage your schedule while maintaining a high bar for responsiveness and customer outcomes.
• 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.

The pay range for this role is $90,000 - $125,000 USD per year.

United States

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