Senior Product Manager, Benefits

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, Benefits based in Italy.

This is a senior, high-autonomy product role focused on building the infrastructure that powers benefits administration globally.

You’ll own a complex portfolio spanning third-party integrations, payroll connectivity, benefits data, compliance, and provider management.

In the near term, you’ll lead high-impact migrations and integrations where data accuracy directly affects employee pay and customer outcomes.

Over time, you’ll shape a unified, provider-agnostic benefits platform that works consistently across multiple employment models and countries.

You’ll collaborate closely with Engineering, Payroll Operations, Finance, Partnerships, and Legal/Compliance in a highly distributed, asynchronous environment.

The role combines strategic product leadership with hands-on technical execution, including prototyping and problem-solving with modern AI coding tools.

It's an opportunity to influence foundational infrastructure while helping define how benefits technology evolves for both human and API-driven users.

• Accountabilities
• Define and own the benefits infrastructure strategy, balancing near-term integration priorities with the long-term vision of a unified, provider-agnostic benefits administration platform.
• Drive the roadmap for integrations with benefits carriers, third-party administrators, benefits platforms, brokers, and customers’ HR systems, determining where to deepen integrations, consolidate solutions, or sunset partnerships.
• Lead complex, cross-functional initiatives from discovery and technical design through testing, migration, launch, and ongoing optimization.
• Oversee initiatives such as migrating benefit costs to unified payroll infrastructure, implementing retirement plan administration, enabling bring-your-own-broker capabilities, and ensuring benefits data from external HR systems flows accurately into payroll.
• Establish robust testing, reconciliation, validation, and go-live processes in partnership with Engineering and operational teams.
• Develop consistent benefits experiences across Employer of Record, global payroll, PEO, and HRIS-connected environments, ensuring core concepts such as eligibility, enrollment, providers, and costs work consistently regardless of data source.
• Build proactive compliance and data-integrity capabilities that identify discrepancies before they affect employees, payroll, or customers.
• Act as the escalation point for benefits-related data incidents, leading root-cause analysis, remediation, and long-term fixes rather than temporary workarounds.
• Develop systemic tools for discrepancy reporting, reconciliation, unmapped-cost detection, and other controls that improve the reliability of benefits infrastructure.
• Own the lifecycle of benefits partnerships, from sourcing and evaluation through integration, performance management, and eventual offboarding.
• Partner with commercial and partnership teams on vendor relationships while serving as a product and technical subject-matter expert with external providers.
• Enable Sales and Implementation teams with reliable benefits-processing workflows, using AI-powered tools and code-connected agents where appropriate to verify provider availability, system behavior, and expected outcomes.
• Communicate product strategy, priorities, and process changes clearly across Product, Engineering, Payroll Operations, Finance, Partnerships, and Legal/Compliance.
• Champion transparent, asynchronous collaboration and maintain alignment across globally distributed teams.

Requirements

• Significant experience as a Product Manager owning complex third-party integrations, particularly API- and file/EDI-based integrations.
• Strong product strategy experience, with the ability to translate complex technical and operational challenges into clear roadmaps and priorities.
• A provider-agnostic mindset and experience designing products that accommodate customers’ existing technology ecosystems, including brokers, carriers, HRIS platforms, and other external providers.
• Proficiency with

Cursor and/or Claude Code , with the ability to independently build, debug, and ship functional code or prototypes rather than relying solely on product specifications.

• Strong technical fluency, including the ability to understand data-mapping specifications, reason about synchronization and reconciliation logic, and engage confidently with engineers on topics such as idempotency, settlement thresholds, and migration sequencing.
• Ability to design for both human users and systems, including APIs, integrations, and agent-facing tooling.
• Strong commercial and strategic judgment, with the ability to make prioritization, consolidation, integration, and partner decisions under real-world deadlines.
• Excellent asynchronous written communication skills and the ability to drive alignment without relying heavily on meetings.
• Proven ability to operate effectively in complex, cross-functional environments involving technical, operational, financial, and compliance stakeholders.
• Strong ownership, autonomy, and problem-solving skills, with a bias toward action and the ability to navigate ambiguity.
• Experience in benefits, HR technology, payroll, insurance technology, fintech, or a related domain is highly valuable.
• Experience managing or negotiating commercial partnerships in addition to technical integrations is a plus.
• Experience working in a globally distributed, remote, and asynchronous organization is advantageous.
• Genuine interest in AI and automation, particularly their application to product development, operational workflows, integrations, and technical problem-solving.

Benefits

• Annual salary range of

USD $59,900-$151,650 , with the final offer determined by location, experience, skills, training, business needs, and market factors.

• Stock options.
• Work-from-anywhere flexibility.
• Flexible working hours within an asynchronous work environment.
• Flexible paid time off.

16 weeks of paid parental leave.

• Budget for co-working spaces, learning, and wellness activities, including gym memberships.
• Mental health support services.
• Home-office budget and IT equipment.
• Compensation philosophy designed to support pay equity and competitive local market rates.
• Opportunity to work with globally distributed teams across multiple countries and time zones.
• Strong autonomy to organize your work around your life and personal commitments.

How Jobgether works

We use an

AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements.

Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company.

The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

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