Deployment Analyst

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 50+ jurisdictions representing nearly 5% of the US population, including major counties around the Bay Area and Los Angeles metro areas. 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 a Deployment Analyst to help our government clients learn, onboard, get unstuck, and to turn specific client projects into decisions they can act on and formalized product capabilities.
• This is a hands-on, builder's role at the intersection of client education, client support, and hands-on analysis.
• We believe it’s great for someone who wants to think through how a govtech product gets into client’s hands and stays useful to them.

What you'll do

Client support (~35% of time)

• Own Holly's help center to keep it current, accurate, and easy to navigate.
• Field and resolve customer support inquiries related to onboarding, from "how do I use this feature" to "can I add more data into the platform."
• Spot patterns throughout client interactions that signal product or training gaps, and surface those internally to remediate.

Client consulting & analysis projects (~35% of time)

• Deliver hands-on consulting & analytics projects for clients, working directly with their workforce data in Holly.
• Scope each project with the deployment team, validate the underlying data, and present findings clients can act on.
• Partner with the product team to turn recurring project work into product capabilities — what you deliver manually today shapes what Holly ships next.

Remote onboarding and training (~30% of time)

• Own and maintain Holly's asynchronous learning modules, plus the materials and trainings the deployment team use in live client sessions.
• Co-host webinars and office hours that train Holly users on platform features.
• QA the platform ahead of client launches to confirm data and functionality work as expected before go-live.

Who You Are

This is a role for someone who's curious, organized, wants to build real systems, and foster strong client relationships.

• Detail-oriented and process-minded. You notice when something's inconsistent or could be templatized, and you fix it.
• Client-empathetic. You care whether someone actually gets unstuck, not just whether a ticket gets closed.
• A clear, careful writer. You can explain something complicated in a way a non-technical person understands.
• Comfortable with a fast-moving, frequently-changing product. You don't need everything to be settled to do good work.
• AI-fluency. You already use AI tools (Claude, ChatGPT, etc.) to draft, organize, and speed up your own work, and you're excited to build that into how this role runs day to day.
• Interest in the public sector, civic tech, or government work is a plus, even without direct experience.

What You'll Get

• Real ownership. From week one, you'll run workstreams that clients directly experience.
• Cross-functional contribution and mentorship. You will work in close coordination with our product and deployment teams, contributing to and getting support from both.
• Build with AI from day one. You have room to use and shape AI tools as a core part of how the role works, not an afterthought.
• Competitive package. $80,000–$100,000 USD base with equity, comprehensive health benefits (platinum plan with vision and dental), 401(k), 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 (30 min)
  • Take-home assignment (~2 hours)
  • Case interview (45-60 min)
  • Onsite at Holly HQ in NYC
• Location: NYC-based, in-person (4 days a week) or remote from the West Coast. Our engineering, product, and deployment teams are mostly based in New York, and we enjoy collaborating in person — so we'd love to have you in the office. Since most of our clients are on the West Coast, we're also open to candidates based there remotely.
• Work Philosophy: We're an early-stage startup serving government clients with real deadlines, and many of our largest clients 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 that may involve late nights, and the occasional fire drill around launches or critical issues too.
• 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.