Senior Product Manager, Benefits

What this job can offer you

Benefits at Remote is becoming the provider-agnostic, payroll-correct, compliance-monitored infrastructure layer that sits underneath every way Remote employs someone — Employer of Record, global payroll, PEO — and, increasingly, underneath any external HR system a customer brings. It stops being a standalone module people click through and becomes a layer other systems build on top of: invisible when it works, indispensable when it doesn't.

Near term, this is a deeply integration-heavy role. You'll take over a live, high-stakes book of work: migrating benefit costs onto a unified payroll system across multiple carrier and broker paths, standing up retirement plan administration for US global payroll, building provider-agnostic cost ingestion so any customer can bring their own broker or carrier, making benefits data flowing out of clients' own HR systems land correctly in payroll, and resolving benefit-cost data-integrity incidents that touch real employee paychecks. This is hands-in-the-data work: reconciliation logic, eligibility files, settlement thresholds, migration sequencing.

Longer term, this is a full-scope experience and unification role. As Remote consolidates fragmented, product-by-product benefits tooling into one administration platform, one cost-ingestion pipeline, and one source of truth, you'll own the vision and roadmap for making benefits behave consistently everywhere — the same primitives (offers, costs, enrollment, providers, statuses) working the same way across 90+ countries and across Employer of Record, global payroll, PEO, and HRIS-connected customers alike. You'll also own how that layer shows up for non-human consumers — APIs and agent-facing tooling — not just for people in a UI.

This is a senior, high-autonomy role reporting into Product leadership, with regular exposure to Engineering, Payroll Operations, Partnerships, Finance, and Legal/Compliance.

What you bring

• Proven experience as a product manager owning complex third-party integrations (API and file/EDI-based)
• A provider-agnostic mindset: you default to ingesting a customer's existing reality, and anticipating their future needs (their broker, their carrier, their HRIS) rather than forcing them onto a fixed set of embedded partners.
• Proficiency in Cursor and/or Claude Code is required. You must be able to autonomously build, debug, and ship functional code/prototypes, not just write specs.
• Comfort designing for systems as well as humans — you think in APIs and agent-facing tooling, not just dashboards, and can justify a feature by whether it makes a pay run more correct or compliant, not just whether it "feels complete."
• Judgment to make both strategic calls (what to consolidate, what to prioritize, what to explicitly stop doing) and tactical ones (scope of a given integration) under real deadline pressure.
• Excellent async written communication — you'll drive alignment across Engineering, Payroll Operations, Finance, Partnerships, and Legal without relying on meetings.
• Bonus: Experience negotiating or managing commercial partnerships, not just technical integrations, as well as experience in related domains benefits, HR technology, payroll, insurance technology, or fintech

Nice to have

• Strong technical fluency: you can read a data-mapping spec, reason about sync and reconciliation logic, and hold your own in a design conversation with engineers about idempotency, settlement thresholds, or migration sequencing.

Key responsibilities

Own the Benefits infrastructure strategy — near-term integrations, long-term unification

• Drive the roadmap for how Remote connects to carriers, third-party administrators, benefits administration platforms, and customers' own HR systems — deciding where we build deeper integrations, where we consolidate, and where we offboard partners that no longer fit.
• Own the longer-term shift from fragmented, product-specific benefits tooling toward one administration platform, one cost-ingestion pipeline, and one consistent experience across Employer of Record, global payroll, and PEO.
• Break strategy into a roadmap that's legible to engineering, operations, and leadership, and keep every investment tied to one bar: does it make a pay run more correct, keep Remote compliant, or help win or retain a customer.

Lead complex, cross-functional integration delivery

• Drive initiatives such as migrating benefit costs onto a unified payroll system across multiple carrier and broker paths, standing up retirement plan administration, building provider-agnostic cost ingestion (bring-your-own-broker), and making benefits data from clients' HR systems land correctly in payroll — from design through go-live.
• Own test planning, end-to-end validation, and go-live readiness for these migrations, partnering closely with engineering.
• Run the standard process for activating new countries and partners end to end: requirements, integration, carrier onboarding, and rollout.
• Enable sales and implementation on benefits processing and set up - via AI tools to support workflows and code-connected agents to verify provider availability, system behavior and expected outcomes.

Build a seamless benefits experience across products

• Own the vision for consistent benefits behavior across Employer of Record, global payroll, and PEO, and for customers who bring their own HR system, so cost, eligibility, and enrollment data flow the same way regardless of employment model or where the data originates.
• Push proactive, systematic compliance monitoring as a real product surface rather than something discovered when a regulator or customer flags it.
• Identify and close the gaps that today force teams or customers to reconcile benefits data manually across products.

Own data integrity across partner integrations

• Be the escalation point for benefit-cost data incidents (e.g. under-collection, discrepancies between offer and payroll), driving root-cause analysis, remediation, and durable fixes rather than one-off patches.
• Champion systemic tooling — discrepancy reporting, unmapped-cost alerting, reconciliation infrastructure — so issues surface before they hit employees or payroll.

Manage the partner portfolio

• Own the full lifecycle of benefits partners: sourcing and evaluation, technical integration, performance monitoring, and offboarding when a partnership is sunset.
• Partner with the Partnerships team on commercial terms and represent Product as the technical subject-matter expert with carriers and platforms.

Communicate and align

• Evangelize the roadmap and process changes across Product, Engineering, Payroll Operations, Finance, and Partnerships.
• Lead by example on asynchronous, transparent collaboration.

Practicals

• You'll report to: Director of Product, Payroll
• Team: Product Management
• Location: Any location, any timezone

Application process

1. Interview with recruiter
2. Interview with hiring manager
3. Live Session
4. Team Interview
5. Bar Raiser interview
6. Offer + Employment Verification Checks