[Remote] Sr. Product Manager, Data Integrations

Note: The job is a remote job and is open to candidates in USA. Lively is a remote-first company that provides modern benefits solutions, including HSAs and related services for employers, consumers, and financial institutions. The company is seeking a Senior Product Manager to own data exchange and integration strategy across its ecosystem, including enrollment and eligibility data, file- and API-based integrations, and AI-assisted onboarding and validation experiences.

Responsibilities

• Integration Ownership — Own the data exchanged between Lively and its partners: what moves, in what form, on what cadence, and what happens when something goes wrong. Define the contracts that both sides build against
• AI-Assisted Data Onboarding & Validation — Own the AI agent experiences that accelerate getting partner and customer data into Lively: interpreting unfamiliar file structures, mapping fields, catching errors before they propagate, explaining what went wrong in language a non-technical administrator can act on, and recommending fixes. Define where the agent acts, where it advises, and where a human must approve
• Enrollment & Eligibility Data — Own the enrollment data lifecycle end to end, including how changes, corrections, and exceptions are handled, and how Lively proves its records match the partner's
• Reliability, Data Quality & Scale — Own the non-functional requirements of Lively's data integration platform: throughput, latency, availability, recovery, and the guarantee that data is never silently lost or partially applied. Define how failures are detected, communicated, and resolved. Plan capacity for the benefits industry's seasonal enrollment peaks and for growth in partner and record volume. Set the accuracy bar AI-assisted validation must clear before production use
• Integration Strategy — Set the multi-year direction for how Lively connects to its ecosystem: the target architecture, the migration path from today's model, the role AI plays in reducing integration effort, and the build/buy/partner decisions that get us there
• Requirements & Discovery — Translate partner needs, customer commitments, and regulatory constraints into clear, complete requirements — including the edge cases and failure paths, not only the intended flow
• Partner & Implementation Enablement — Support the technical onboarding of new partners from specification through go-live, and reduce the time and effort each new connection takes
• Stakeholder Stewardship — Act as the primary SME for your areas, fielding questions from implementation, customer success, sales, and leadership. Communicate vision, roadmap, and progress to internal and external audiences
• Roadmap Ownership — Sequence complex, multi-quarter integration work into delivery milestones, balancing customer commitments, partner dependencies, and platform health
• Performance Tracking — Define and monitor the metrics that describe integration health, onboarding effort, and AI agent accuracy, and use them to direct investment
• AI Fluency in Practice — Use AI tooling in your own product work — research, specification, data analysis, prototyping — and raise the bar for how the product organization does the same
• Market Awareness — Track how the benefits, payroll, and data-interoperability landscape is evolving, including where AI is changing what integration work costs, and identify partnership and standardization opportunities

Skills

• 5+ years of product management experience, with meaningful time owning integrations, data exchange, or platform APIs as a primary product surface
• Experience owning the exchange of structured business data between organizations — whether by file, API, or both — including the formats, cadence, and correctness guarantees each side depends on
• Demonstrated ownership of API products, including how they are designed, documented, evolved, and eventually retired without disrupting the partners built on them
• Strong judgment about data reliability at scale — you think in terms of what happens when a feed is late, incomplete, duplicated, or wrong, and you design for those cases deliberately
• Experience working directly with external technical partners — you can hold a substantive conversation with a partner's engineering team and represent Lively's position credibly without an engineer in the room
• Technical depth sufficient to be self-sufficient — you investigate data questions yourself rather than routing every one to engineering, and engineers regard your specifications as complete
• Experience handling sensitive personal or financial data under a regulated framework, with an instinct for privacy, security, and auditability
• Excellent analytical and problem-solving skills, with the ability to synthesize complex data into clear product decisions
• Outstanding communication skills — you can align engineers, partners, and executives on a shared direction
• Strong familiarity with Agile methodologies and standard product tooling
• Bachelor's degree in a technical or business field, or equivalent practical experience
• Benefits or health insurance domain experience — HSA/FSA/HRA plans, benefits compliance, IRS regulations, or the administration workflows behind them
• Ecosystem familiarity with payroll providers, HR platforms, benefits administration systems, carriers, or third-party administrators
• Fluency with industry data standards used in benefits, insurance, healthcare, or financial services exchange
• Experience modernizing a legacy integration surface — migrating partners onto a new model without breaking the old one
• Experience evaluating integration and connectivity vendors, and owning the build/buy/partner decision
• Experience building AI-powered product experiences, including designing for reliability and user trust
• Experience spanning both B2B (employer/broker-facing) and B2C (employee-facing) products
• Leadership experience, including mentoring or developing junior PMs
• Growth mindset and high self-motivation — you identify the next problem rather than waiting for it to be assigned

Benefits

• Stock options
• Medical coverage
• Dental coverage
• Vision coverage
• Life coverage
• Disability coverage
• An HSA with employer contribution
• FSA
• Paid parental leave
• Medical travel benefits
• A 401k plan
• Flexible vacation policy
• Lifestyle spending accounts

Company Overview

Company H1B Sponsorship