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Salary: USD 165,000 - 195,000 / annual
Lively is a benefits technology company that modernizes how employers and employees manage health savings accounts (HSAs) and related benefits. The company combines user-centric design with innovative technology to simplify benefits administration.
You will own the data integration layer that connects Lively's platform to the broader benefits ecosystem—payroll systems, HR platforms, benefits administration systems, carriers, and third-party administrators. This encompasses enrollment and eligibility data flows, file-based and API-based exchange, and the strategic roadmap for ecosystem connectivity.
Key responsibilities include:
**Integration Ownership**: Define and manage all data exchanged between Lively and partners—what moves, in what form, on what cadence, and failure handling. Establish the contracts both sides build against.
**AI-Assisted Data Onboarding & Validation**: Own AI agent experiences that accelerate partner and customer data ingestion. Agents interpret unfamiliar file structures, map fields, catch errors, explain failures in non-technical language, and recommend corrections. You decide where agents act autonomously, where they advise, and where human approval is mandatory.
**Enrollment & Eligibility Data**: Manage the complete lifecycle of enrollment data, including changes, corrections, exceptions, and reconciliation between Lively and partner records.
**Reliability & Data Quality**: Own non-functional requirements—throughput, latency, availability, recovery, and guarantees against silent data loss or partial application. Define failure detection, communication, and resolution. Plan for seasonal peaks and growth. Set accuracy thresholds for AI-assisted validation.
**Integration Strategy**: Set multi-year direction for ecosystem connectivity—target architecture, migration paths, AI's role in reducing integration effort, and build/buy/partner decisions.
**Requirements & Discovery**: Translate partner needs, customer commitments, and regulatory constraints into complete requirements, including edge cases and failure paths.
**Partner & Implementation Enablement**: Support technical onboarding of new partners from specification through go-live. Reduce time and effort for each new connection.
**Stakeholder Stewardship**: Serve as primary subject matter expert for your areas. Field questions from implementation, customer success, sales, and leadership. Communicate vision, roadmap, and progress internally and externally.
**Roadmap Ownership**: Sequence complex, multi-quarter integration work into delivery milestones, balancing customer commitments, partner dependencies, and platform health.
**Performance Tracking**: Define and monitor metrics describing integration health, onboarding effort, and AI agent accuracy. Direct investment based on data.
**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 operates.
**Market Awareness**: Track evolution of benefits, payroll, and data-interoperability landscapes, including how AI changes integration costs. Identify partnership and standardization opportunities.
This is a technically grounded role. You will work closely with engineering on system behavior, data design, and agent behavior. You will be the person partners and internal teams consult when they need to understand how data actually flows. You will own large initiatives end-to-end and operate as the primary subject matter expert for your areas.
Note: Candidate preference will be given to those in Pacific and Mountain timezones, as the majority of the engineering team is based in Pacific time.
**REQUIREMENTS**
Required Qualifications:
- 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 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
What Sets You Apart:
- 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
