Senior Product Manager

Role overview Drive the strategy and delivery of a global benefits infrastructure layer that powers employer-of-record, payroll, and PEO products across 90+ countries. The role splits between near-term, integration-heavy execution (migrations, retirement plan rollout, provider-agnostic cost ingestion) and longer-term unification of fragmented benefits tooling into one administration platform. It is a senior, high-autonomy product position with regular cross-functional exposure to Engineering, Payroll Operations, Partnerships, Finance, and Legal/Compliance.

Responsibilities - Define and own the multi-quarter roadmap for how the platform connects to carriers, third-party administrators, benefits platforms, and customers' own HR systems, deciding where to deepen integrations, consolidate, or offboard partners. - Drive complex integration programs such as migrating benefit costs onto a unified payroll engine across multiple carrier and broker paths, standing up retirement plan administration, and building bring-your-own-broker cost ingestion. - Lead consolidation of fragmented benefits tools into one administration platform, one cost-ingestion pipeline, and one consistent experience across employment products. - Own test planning, end-to-end validation, and go-live readiness for migrations and new integrations, partnering closely with engineering. - Make both strategic calls (what to consolidate, what to stop) and tactical calls (scope of a specific integration) under real deadline pressure. - Champion a provider-agnostic mindset so the platform can ingest each customer's existing reality rather than forcing them onto embedded partners.

Requirements - Proven experience as a product manager owning complex third-party integrations spanning both API and file/EDI-based patterns. - Comfort designing for systems as well as humans, with API- and agent-facing tooling experience, not just dashboard work. - Hands-on proficiency with AI coding assistants such as Cursor and/or Claude Code, including the ability to autonomously build, debug, and ship working code or prototypes. - Strong technical fluency: ability to read data-mapping specs, reason about sync and reconciliation logic, and discuss idempotency, settlement thresholds, or migration sequencing with engineers. - Excellent asynchronous written communication, with a track record of aligning engineering, operations, finance, and legal partners without relying on meetings.

Nice to have - Background in benefits, HR technology, payroll, insurance technology, or fintech. - Experience negotiating or managing commercial partnerships alongside technical integrations.

Benefits and work setup - Fully remote, asynchronous-first work culture with flexible hours and the ability to plan around personal life. - Flexible paid time off, 16 weeks of paid parental leave, and mental health support services. - Stock options, a learning budget, and a home office / IT equipment budget. - Budget for local in-person social events or co-working spaces. - Annual base salary range of $59,900–$151,650 USD, depending on location, level, and experience.