Position Summary 

Lead Director, Technology Product Management is accountable for the product vision, roadmap, and delivery of technology capabilities that enable the end-to-end Medicare insurance product lifecycle. This role leads product strategy and execution within a highly regulated Medicare ecosystem, driving operational accuracy, efficiency, and readiness for CMS requirements across the annual cycle (plan design, bid submission, and member materials). 

You’ll partner across multiple product teams and with key vendor partners to improve product health, deliver measurable value, and advance targeted outcomes. You’ll work closely with the Business General Manager (GM), Design, Engineering, and Data/Analytics as part of the “Five in a Box” product leadership team, and you’ll collaborate with stakeholders including architecture, tech-ops, security, and others to ensure cohesion across the Medicare technology product line. 

This role begins as an individual contributor and transitions to leading and developing a team of product management colleagues, with a focus on strong product thinking, operational awareness of Medicare timelines and dependencies, and the ability to translate complex regulatory and business processes into intuitive, reliable, high-quality technology solutions. 

Key Responsibilities:

Product vision, strategy, and roadmaps 

• Define and socialize product vision, strategy, and roadmap with the “Five in a Box” leadership team; continually assess and refine based on learning and outcomes. 

• Partner with the Business GM and stakeholders to set investment priorities and build business cases. 

• Translate customer, business, and technology needs into epics and initiatives tied to targeted outcomes. 

• Connect roadmap decisions to value drivers that support business priorities, OKRs, and strategic programs. 

• Align roadmaps, backlogs, capacity, timelines, and delivery commitments across product areas. 

• Define and track product OKRs aligned to business outcomes to measure progress and impact. 

Backlog ownership, work definition, and prioritization 

• Set direction for discovery work and ensure continuous exploration of customer and business needs. 

• Define features, identify dependencies, and partner with teams to size and plan work for upcoming quarters. 

• Facilitate product-level ceremonies and meetings, including quarterly PI planning activities (as applicable). 

Trend monitoring, product performance, and value delivery 

• Use performance data to identify issues quickly and form hypotheses about product health, technical health, and customer feedback. 

• Track and socialize progress against OKRs and metrics; reinforce alignment to broader portfolio outcomes. 

• Coordinate product launches (beta testing, user feedback, documentation). 

• Ensure learnings from discovery and delivery are captured and prioritized in the backlog. 

Cross-functional teaming and stakeholder management 

• Facilitate strong operating rhythms across the “Five in a Box” team, including close partnership with the Business GM. 

• Ensure business strategies and targeted outcomes are understood and adopted by product teams. 

• Partners with business and customer insight teams to understand market and customer needs. 

• Showcase product delivery, outcomes, and decisions to stakeholders across levels. 

Grow and develop the team 

• Understand the hiring market and identify candidates with the right mix of skillset and leadership style. 

• Champion strong product management and agile mindsets; communicate wins, learnings, and opportunities. 

• Build and coach high-performing product teams (Product Managers, Product Leads, Product Owners, etc.), including norms for how teams operate. 

• Promote a customer-centric culture grounded in product performance visibility, clear “north star” direction, and proactive communication of product health metrics. 

Required Qualifications: 

• 10+ years of experience in product management (Product Manager, Product Owner, Business General Manager, or related to managed healthcare insurance roles) with emphasis on strategy and roadmaps. 

• 5+ years of software product management experience delivering multiple releases end-to-end (discovery through launch) in an agile environment. 

• 3+ years of experience with Medicare insurance product design and/or implementation (Individual or Group). 

• 3+ years of experience coaching, mentoring, performance management, and/or leading teams. 

• 3+ years of experience with data insights, gathering and reporting.  Data-driven decision making and quantitative analysis skills (e.g., Jira). 

• Able to work east coast business hours. 

Preferred Qualifications: 

• Experience with Medicare bid creation and filing (Individual). 

• Experience with Medicare group plan creation. 

• Experience with Medicare member materials creation and management (ANOC/EOC/SOC/NMK). 

• Experience with supplemental benefit management and CMS reporting requirements. 

• Experience with Medicare Part D formulary processes. 

• Experience with automated validation of Medicare plan data. 

• Strong operational awareness of Medicare timelines and dependencies. 

• Ability to translate complex regulatory and business processes into intuitive, reliable, high-quality technology solutions. 

• SAFe experience. 

• Ability to drive cross-functional alignment amid ambiguity. 

• Strong negotiation, organizational, management, analytical, and people skills. 

• General understanding of core programming and computer science concepts, including AI/ML. 

• Advanced written and verbal communication skills, with ability to influence stakeholders across levels. 

Education: 

• Bachelor’s degree or equivalent work experience.