Sr. Product Manager

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. 

WHAT YOU'LL DO 

Responsibilities are listed in order of anticipated time investment: 

• 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. 

WHAT WE'RE LOOKING FOR 

Required Qualifications 

• 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 

What Sets You Apart 

• 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 

WHAT SUCCESS LOOKS LIKE 

In your first 90 days and beyond, a great Senior PM at Lively will demonstrate: 

1. Strategic Product Vision 

• Develops a comprehensive product strategy for assigned areas that aligns with company  OKRs 
• Articulates a clear and compelling product vision to stakeholders at every level • Drives successful realization of strategic initiatives through disciplined execution 

1. Roadmap Execution 

• Creates and maintains a detailed, well-prioritized roadmap with clear delivery milestones • Ships high-quality products on time with strong adoption and positive user feedback • Phases complex projects into manageable increments without losing sight of the long term vision 

1. Customer & Market Intelligence 

• Develops deep empathy for user personas through regular research and feedback loops
• Translates customer insights and market trends into product bets with clear business  rationale 
• Drives measurable improvements in customer satisfaction, retention, and engagement 

1. Cross-Functional Leadership 

• Earns the trust of engineering, design, and go-to-market partners through clarity and  follow-through 
• Communicates requirements, priorities, and trade-offs in ways that create shared ownership
• Receives consistently positive feedback from peers and stakeholders on collaboration  and leadership 

1. Performance & Impact 

• Defines meaningful KPIs for product areas and tracks them with rigor • Continuously analyzes product data to identify improvements and surface insights for  leadership 
• Achieves target metrics and contributes to measurable business growth 

1. Team Development 

• Actively mentors junior PMs and contributes to a culture of high standards and  continuous learning 
• Fosters psychological safety and intellectual curiosity within the product organization
• Leads by example: writes great specs, runs tight reviews, and raises the quality bar 

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 

Lively is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all  employees.

Applicants must be currently authorized to work in the United States on a full-time basis with no sponsorship needed now, or in the future.