Associate Product Manager, AI & Automation

Associate Product Manager, AI & Automation

ProService is a Hawaii-based Professional Employer Organization (PEO) that provides payroll, HR consulting, benefits administration, and back-office support to small and medium-sized businesses across the United States. We serve as an extension of our clients' teams - we handle the operational complexity so they can focus on running their businesses. ProService is backed by Silver Lake, one of the leading global technology investors.

We're growing our AI and automation team with a new kind of role, one driven by analytical, operationally minded people using AI-assisted development (primarily Claude Code) to rapidly build and ship tools. We're hiring 2-3 Associate Product Managers, AI Automation to join our team and take tools from idea through production. This is a hands-on role: you'll be building and shipping products, not writing slide decks.

Why This Role

This role is built for people who are excited about AI but don't necessarily come from an engineering background. You'll learn how to develop real software using AI-assisted tools like Claude Code - a skillset that's rapidly becoming one of the most valuable in the market - while leveraging the analytical and problem-solving strengths you already have.

We operate with extremely fast iteration cycles and believe in showing, not telling. You'll build something, ship it, and see it in the hands of real users within weeks, not quarters, all without making any slide decks.

What You'll Do

• Build automation tools using Claude Code and AI-assisted development � scoping problems, leading development, validating output, and iterating to production-ready solutions.
• Own the full lifecycle from identifying a process worth automating, writing product requirements, and leading prototyping and testing coordination with business stakeholders, and deployment.
• Work directly with business teams to understand workflows, pain points, and edge cases � then translate that understanding into well-designed automation.
• Navigate data and systems � understand where data lives (Snowflake, Prism, internal databases), how systems integrate, and how to design tools that handle real-world messiness.
• Contribute to the operating model � this is a new role on a rapidly growing team. You'll help refine how we operate, prioritize, build, test, document, and maintain automation tools as the practice scales.
• Document and maintain what you build, including test plans, tool manifests, and dependency tracking so the work is sustainable beyond any one person.

Who You'll Work With

• Mikaela Ferguson, Director of AI Products � your direct manager and the person leading AI and automation efforts across ProService. You'll partner closely with her on prioritization, methodology, and day-to-day direction of the work.
• VP Engineering and AI Software Engineers � you'll work with the engineering team to bring your prototypes to production. You'll collaborate on architecture decisions, security requirements, and integration patterns.
• Business leaders across service teams � including Benefits, Payroll, and Support. You'll embed with these teams to understand why a process exists, where the pain points are, and how it can be improved. Their domain expertise is the starting point for everything you build.
• Enablement � once a tool is production-ready, you'll provide support to the Enablement team so they can roll out your products across the organization and train end users. They'll also be a resource for reviewing adoption metrics and tracking measurable impact.

This role is central to ProService's 2026 strategic goals and carries visibility with the executive leadership team. The work you do will directly influence how the company operates and scales.

Who You Are

You've spent at least 3 years in an analytically rigorous role and are looking to make the transition into product management. You're analytical, structured, and fast � you know how to break down messy problems, build frameworks, and move quickly from ambiguity to action.

• Excited about AI applications - Most importantly, you should be excited about the fast-evolving capabilities of AI and AI-assisted coding platforms. Writing prompts and seeing your ideas immediately on the screen should make you excited!
• Technically curious, not necessarily technical. You don't need to be a software engineer. But you're comfortable - or eager to learn - reasoning about code, data structures, APIs, and system design. SQL or light programming experience is a plus but not required.
• Analytical and process-oriented - you can zoom in and out. You won't be responsible for process re-design, but you will be responsible for the AI and automation solutions within the new process. You're comfortable with digging into a problem to get to the root cause, and coming up with solutions to fix them, but can still see the bigger picture and think strategically.
• Comfortable with ambiguity. This is a new function. The operating model is still being refined. You'll help shape it, not just execute a playbook.
• Strong communicator. You'll work across business teams, engineering, and leadership. You need to translate between technical and non-technical audiences fluently.
• Bias toward building. You'd rather ship something imperfect and iterate than spend weeks on a deck. You're energized by making things work, not just analyzing them.
• Self-directed. This is a remote role with a small, fast-moving team. You manage your own time and flag blockers early.

Nice to Have (But Not Required)

• Technical undergraduate degree (Engineering, Math, Computer Science, Science, etc.)
• Experience with AI-assisted development tools (Claude Code, GitHub Copilot, Cursor, etc.)
• SQL proficiency or basic programming skills (Python, JavaScript, or similar)
• Background in HR tech, PEO, payroll, or benefits administration
• Experience with process automation, RPA, or internal tooling
• Familiarity with AWS or basic cloud infrastructure concepts

Working Arrangement

This role is available as a full-time freelance/contract engagement. It is fully remote, and we are open to candidates based in the United States or Canada. We have a preference for candidates in Mountain and Pacific time zones, or willing to work within these timezones, since we have team members across Hawaii and the Mainland and want to maximize overlap with them.

There may be occasional travel to Denver, the San Francisco Bay Area, or Honolulu for team working sessions. Compensation is commensurate with experience and will be discussed during the interview process.