Sr. Product Manager

Lively • San Francisco, CA

23h • Remote

About The Position

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.
We are seeking an experienced and strategic Senior Product Manager to join our growing team. In this role, you'll lead product strategy and delivery across Lively's B2B and B2C product surfaces — from the employer dashboard and broker portal to the employee-facing app and AI powered agent experiences. You'll work at the intersection of healthcare benefits, financial technology, and applied AI, shaping products that directly improve the financial wellbeing of working Americans.
This is a high-impact, high-autonomy role. You'll own large initiatives end-to-end, drive cross functional alignment, and operate as the primary subject matter expert for your product areas. If you thrive in fast-paced environments, love ambiguity, and have strong opinions about what it means to build truly great product, we want to meet you.

Requirements

• 5+ years of product management experience, with a proven track record of launching and managing software products
• Domain experience in healthcare benefits, health insurance, fintech, or financial services — you understand HSA/FSA/HRA plans or can ramp quickly
• Bachelor's degree in Business, Marketing, Computer Science, or a related field (MBA is a plus)
• Strong familiarity with Agile development methodologies and the full product lifecycle
• Excellent analytical and problem-solving skills, with the ability to synthesize complex data into clear product decisions
• Deep understanding of choice architecture and how product design influences user behavior
• Outstanding communication and interpersonal skills — you can align a room of engineers, designers, and executives on a shared direction
• Experience with product management tools such as Jira, Aha!, or similar
• Familiarity with analytics platforms (Google Analytics, Mixpanel, Amplitude, or similar) and user testing methodologies
• Leadership experience, including mentoring or developing junior PMs

Nice To Haves

• Experience building AI-powered product experiences — you've shipped LLM-based features, intelligent agents, or AI-assisted workflows and understand how to design for AI reliability, safety, and user trust
• Comfort operating in a fast-paced, AI-augmented product environment where tools, processes, and possibilities are evolving quickly
• Growth mindset and high self-motivation — you don't wait to be told what the next problem is
• Genuine innovation instinct — you bring new ideas to the table, not just execution on someone else's roadmap
• Experience spanning both B2B (employer/broker-facing) and B2C (employee/consumer facing) products
• Understanding of benefits compliance, IRS regulations, or financial data handling is a meaningful plus

Responsibilities

• Product Development: Lead the development process for one or more large initiatives, working closely with engineering, design, QA, and project management to ensure high-quality, on-time delivery.
• Requirements & Discovery: Collaborate with stakeholders to gather, define, and refine product requirements — ensuring clarity, alignment, and measurable impact before a line of code is written.
• Product Strategy: Develop and execute product strategies that align with company goals and market realities. Understand the competitive landscape, key user problems, and existing solutions. Lead build vs. buy vs. partner evaluations.
• Stakeholder Stewardship: Communicate product vision, roadmap, and initiative progress to internal and external stakeholders. Act as the primary SME for your product ownership areas — fielding questions from CS, sales, and leadership with confidence.
• Roadmap Ownership: Sequence and phase large projects into delivery milestones. Create and manage a detailed roadmap, prioritizing features based on customer feedback, market research, and business objectives.
• Customer Insights: Conduct user research and gather customer feedback to continuously inform product decisions. Deeply understand key personas and their real-world workflows.
• Market & Competitive Analysis: Monitor trends in healthcare benefits, fintech, and AI tooling to identify emerging opportunities, competitive threats, and adjacent use cases.
• Launch & Enablement: Partner with marketing on go-to-market strategy and materials. Lead internal product training and business readiness for rollouts.
• Performance Tracking: Define and monitor KPIs and product health metrics. Use data to identify gaps, celebrate wins, and drive continuous improvement.

Benefits

• 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!

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 11-50 employees