Sr. Product Manager, Data Integrations (PST/MST)

About Lively

Lively set out to raise the bar on benefit solutions, because we believe no one should have to sacrifice personal wellness for financial wellness. While traditional benefits focus more on transactions and less on the humans using them, Lively harnesses user-centric design and innovative technology to deliver an effortless experience for employers and account holders alike. Our modern HSA is consistently top-rated, and we have since expanded our offerings to provide a full suite of other benefits and services for companies, consumers, and financial institutions.

Lively is a remote-first company, headquartered in San Francisco with employees across the US. Come join us and help make getting the value out of your benefits as simple as it should be.

THE ROLE

Lively is hiring a Senior Product Manager to own how data moves between our platform and the systems our customers and partners rely on — payroll and HR platforms, benefits administration systems, carriers, and third-party administrators. You will own enrollment and eligibility data, file-based and API-based exchange, and the integration roadmap that connects Lively to its ecosystem.

You will also own the AI agent experiences that sit on top of that data layer, with a focus on onboarding and validation: agents that help customers and partners get their data into Lively correctly the first time, interpret what arrives, surface problems in plain language, and propose corrections. Integration work at Lively is increasingly AI-assisted, and this role decides where that assistance belongs and where human review stays mandatory.

Alongside this, you will shape Lively's forward data integration strategy: how our connectivity model evolves as the ecosystem moves toward real-time exchange, where we invest in building versus partnering, and how we make each additional integration cheaper and faster than the last.

This is a technically grounded product role. You will work closely with engineering on system behavior, data design, and agent behavior, and you will be the person partners and internal teams come to when they need to understand how the data actually flows. You will own large initiatives end-to-end and operate as the primary subject matter expert for your areas.

Please note: As a majority of our engineering team sits in Pacific time, candidate preference will be given to those in the Pacific and Mountain timezones. 

WHAT YOU'LL DO

Responsibilities are listed in order of anticipated time investment:

• 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.

WHAT WE'RE LOOKING FOR

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 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

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

WHY LIVELY 

Healthcare and financial benefits affect everyone — and most platforms in this space are still  frustratingly hard to use. Lively exists to change that. You'll work on products that matter, with a team that cares about craft, velocity, and outcomes. 

What you can expect: 

• A fast-paced, AI-augmented product environment where you'll work with cutting-edge tools daily 
• Meaningful ownership — this is not a role where you're handed a backlog and told to groom it 
• A collaborative, intellectually honest culture where good ideas win regardless of  seniority 
• Direct impact on products used by thousands of employers and millions of employees
• Competitive compensation, comprehensive benefits (yes, we eat our own cooking), and  remote-friendly flexibility

We encourage you to apply even if you do not meet all of the qualifications, but feel you would be a good fit for the position.

Benefits & Perks

We offer competitive salaries, stock options, medical, dental, vision, life and disability coverage. An HSA with employer contribution, FSA, paid parental leave, medical travel benefits, a 401k plan, flexible vacation policy, lifestyle spending accounts, and more!

At Lively, we believe having diverse teams in which everyone can be their authentic self is key to our success. We encourage people from underrepresented backgrounds to apply.  Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.  Come join us in our mission to help people optimize their healthcare spending, maximize their savings, and better their livelihood!

Lively Inc. participates in the E-Verify program. Learn more about E-Verify here:

https://e-verify.uscis.gov/web/media/resourcesContents/E-Verify_Participation_Poster_ES.pdf

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