Senior Product Manager

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Product Manager based in Italy.

This is a high-autonomy product leadership role focused on building the infrastructure that powers global benefits administration and payroll.

You will shape how benefits data, costs, eligibility, enrollment, and provider information move across products, partners, and customer systems.

The role combines strategic product ownership with hands-on delivery of complex integrations, migrations, and data workflows.

You will work closely with Engineering, Payroll Operations, Finance, Partnerships, and Legal to turn fragmented systems into scalable, reliable infrastructure.

A major part of the role involves improving data integrity and ensuring benefits information supports accurate and compliant pay runs.

Over time, you will help create a unified, provider-agnostic benefits platform that works consistently across global employment models and markets.

The environment is fully remote, asynchronous, international, and highly ownership-driven, with significant exposure to senior product and cross-functional leadership.

Accountabilities

• Own the product strategy and roadmap for benefits infrastructure, balancing near-term integration needs with the longer-term goal of creating a unified administration platform, cost-ingestion pipeline, and consistent benefits experience.
• Drive integrations with benefits carriers, third-party administrators, benefits platforms, brokers, and customers’ HR systems, determining where to deepen integrations, consolidate capabilities, or sunset partners.
• Lead complex initiatives from discovery and design through testing, launch, and post-launch stabilization, including benefit-cost migrations, retirement plan administration, provider-agnostic cost ingestion, and HRIS-to-payroll data flows.
• Own end-to-end test planning, validation, migration sequencing, reconciliation logic, and go-live readiness in close partnership with Engineering and operational teams.
• Establish and improve the process for activating new countries and partners, covering requirements, integrations, carrier onboarding, testing, and rollout.
• Enable Sales and Implementation teams with better benefits-processing workflows, using AI-assisted tools and code-connected agents to verify provider availability, system behavior, and expected outcomes.
• Define consistent benefits behavior across Employer of Record, global payroll, PEO, and customers using their own HR systems, ensuring costs, eligibility, enrollment, providers, and statuses behave consistently across employment models.
• Develop proactive compliance monitoring as a product capability and identify gaps that currently require manual reconciliation across products or teams.
• Act as the escalation point for benefits data-integrity incidents, including discrepancies between benefit offers and payroll or under-collection issues, leading root-cause analysis, remediation, and durable product fixes.
• Champion systemic data-quality tooling such as discrepancy reporting, unmapped-cost alerts, and reconciliation infrastructure to identify issues before they affect employees or payroll.
• Own the full lifecycle of benefits partnerships, from sourcing and evaluation through technical integration, performance monitoring, and eventual offboarding.
• Partner with commercial teams on partner relationships and serve as the technical product subject-matter expert when working with carriers, platforms, and other external providers.
• Communicate product strategy, roadmap decisions, process changes, and priorities clearly across Product, Engineering, Payroll Operations, Finance, Partnerships, and Legal.
• Lead by example in asynchronous collaboration, creating alignment through clear written communication and transparent decision-making.

Requirements

• Proven experience as a Product Manager owning complex third-party integrations, particularly API-based and file/EDI-based integrations.
• Strong provider-agnostic product mindset, with the ability to design solutions around customers’ existing brokers, carriers, HRIS platforms, and future technology needs rather than relying exclusively on fixed partner ecosystems.
• Demonstrated ability to operate across both product strategy and technical delivery, including the ability to understand data flows, integration requirements, reconciliation logic, and system dependencies.
• Proficiency with Cursor and/or Claude Code is required, including the ability to independently build, debug, and ship functional code or prototypes rather than using AI tools solely for specification or documentation.
• Strong systems thinking, with the ability to design for both human users and machine consumers through APIs, automation, and agent-facing tooling.
• Ability to evaluate product decisions through measurable business and operational outcomes, particularly accuracy, payroll correctness, compliance, customer retention, and implementation efficiency.
• Strong judgment under deadline pressure, with the ability to make both strategic decisions about priorities and consolidation as well as tactical decisions about individual integration scope.
• Excellent asynchronous written communication skills and the ability to align Engineering, Payroll Operations, Finance, Partnerships, Legal, and other stakeholders without relying heavily on meetings.
• Strong stakeholder management and cross-functional collaboration skills, with the ability to build alignment across technical and operational teams.
• Experience working with complex data mappings, synchronization, reconciliation, migration sequencing, or similar technical product concepts is highly desirable.
• Experience negotiating or managing commercial partnerships in addition to technical integrations is a plus.
• Background in employee benefits, HR technology, payroll, insurtech, fintech, or another closely related domain is a plus.
• Strong technical fluency, including the ability to read data-mapping specifications and discuss concepts such as idempotency, settlement thresholds, synchronization, reconciliation, and migration sequencing with engineers.
• Comfortable working autonomously in a fully distributed, international environment with a strong bias toward action and ownership.

Benefits

• Annual salary range of $59,900-$151,650 USD, with actual compensation determined by factors including role level, location, relevant skills, experience, training, business needs, and market conditions.
• Fully remote work from Romania, with the ability to work from anywhere within the applicable employment framework.
• Flexible working hours and an asynchronous work model designed to let employees structure their schedules around their lives.
• Flexible paid time off.
• 16 weeks of paid parental leave.
• Budget for coworking spaces, learning, and wellness activities, including gym memberships.
• Mental health support services.
• Stock options.
• Home-office budget and IT equipment.
• Global, distributed work environment spanning multiple countries and time zones.
• Significant autonomy and ownership within a senior product organization.
• Opportunity to work on complex global payroll, benefits, compliance, and HR technology infrastructure.
• Exposure to AI-powered product development and modern automation capabilities.
• Strong emphasis on professional growth, internal mobility, and fair, location-aware compensation practices.
• Inclusive environment that encourages employees from diverse backgrounds and supports employee resource groups and workplace accommodations.