Deployment Strategist

About the Opportunity

• We're hiring a Deployment Strategist as we scale from 50 to 150+ government clients. 

• You'll 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, you'll be managing 2–3 simultaneous launches. You'll frequently be in rooms with two to twenty public servants, many of them using AI for the first time. You're their entry point - and you'll 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 you'll 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. You’ll 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 — what's confusing, what's 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.
• You're a strong project manager who follows through. You ask good questions, stay close to the details, and don't consider a launch successful until the client is actually getting value.
• You're 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).
• You're entreprenurial and proactive, with a natural inclination to understand how things can be done better (especially through the use of different technologies) and a bias toward action.

What You'll 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 – you're not just executing a playbook, you're 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), 401(k) benefits, 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:We’re 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.