At H&R Block, Product Management is helping shape the future of how clients and tax pros experience tax, financial confidence, advice and AI-enabled service. The Senior Director, Product Management – Explorations will lead multiple new teams focused on early-stage discovery, Horizon 3 growth opportunities, and AI-enabled ways of working that help identify the next differentiated growth areas before the organization commits to scaled investment. 

This leader will bring deep product craft, strong discovery discipline, and the ability to create clarity in ambiguous spaces. They will be both a player engaged in Discovery and a coach to facilitate broad discovery across business lines, guide teams through structured learning agendas, and help move promising ideas from insight to validated concept to scaled testing within the appropriate product pillar. The role will translate strategic priorities and Ideal State themes into a disciplined Explorations portfolio with clear OKRs, learning goals, business cases, and decision gates. This role requires a product leader who can operate with entrepreneurial urgency while navigating the realities of a large, regulated enterprise. 

You’ll also be an integral part of the H&R Block Product Leadership team contributing to the overall product strategy, special initiatives and team culture.  

What You’ll Do... 

Lead Explorations and Discovery 

• Lead broad, early-stage discovery across new product opportunities, and AI-enabled client or associate experiences. 

• Define and manage learning agendas that clarify the customer problem, target segment, differentiated value proposition, feasibility, desirability, viability, commercial potential, compliance considerations, and path to scale. 

• Design and guide lightweight experiments, prototypes, and behavioral signal-gathering methods that produce clear go/no-go recommendations. 

• Own the path from discovery through validated concept, including experiment execution, executive recommendations, and clean transition plans to the appropriate core product pillar when opportunities are ready for scaled delivery. 

• Maintain a disciplined bias toward small teams, fast learning cycles, and evidence-based decision-making before scaled investment. 

• Build and evaluate business cases for exploratory opportunities, including market sizing, customer impact, cost/benefit analysis, investment requirements, risk, and potential KPI or P&L impact. 

• Partner with leaders across Product, Design, Engineering, Marketing, Retail, Legal, Risk, Data, and Finance to ensure explorations are grounded in customer needs, business outcomes, and enterprise constraints. 

Bring world-class Product Craft and Coaching 

• Set a high bar for product management craft, including customer discovery, problem framing, outcome definition, opportunity sizing, prioritization, experimentation, and storytelling. 

• Coach product managers and cross-functional teams on how to move from ideas and opinions to testable hypotheses and measurable customer or business outcomes. 

• Lead, coach, and develop product managers and product leaders, modeling strong product craft and creating a high-performing Explorations team. 

• Translate ambiguous strategic opportunities into crisp decision narratives, learning plans, and executive-ready recommendations. 

• Model strong judgment in balancing exploration with focus, ensuring teams avoid premature scaling or overbuilding before meaningful signal exists. 

• Help raise the overall product culture by demonstrating curiosity, accountability, customer obsession, and disciplined learning velocity. 

• Evangelize discovery, experimentation, and AI-enabled product practices across the broader Product organization, helping define what “great” looks like for modern product management at H&R Block. 

Facilitate and Lead Cross-Functional Teams 

• Facilitate complex, cross-functional working sessions that bring together diverse perspectives and move teams toward clear decisions, next steps, and owners. 

• Create the operating rhythm for the Explorations team, including discovery reviews, learning readouts, prioritization forums, and handoff mechanisms to core product pillars. 

• Lead through influence across senior stakeholders, creating alignment without relying solely on reporting authority. 

• Operate as a strong matrix leader and bridge builder, gaining support, resources, and alignment across Product, Design, Technology, Marketing, Retail, Data, Finance, Legal, Risk, and executive stakeholders. 

• Build trust with business and functional leaders by surfacing risks, tradeoffs, dependencies, and decision points early and clearly. 

• Ensure teams stay focused on the highest-value questions and avoid drifting into coordination-heavy activity without measurable learning. 

Advance AI Enablement and New Ways of Working 

• Identify and apply AI-enabled methods to accelerate discovery, research synthesis, prototyping, analysis, product documentation, and experimentation. 

• Partner with technology, data, legal, risk, and enterprise AI enablement teams to ensure experiments and AI-enabled workflows operate within appropriate guardrails. 

• Explore product opportunities where AI agents, automation, and data-driven personalization can create differentiated value for clients, tax pros, and associates. 

• Serve as a visible product leader who models AI fluency, practical experimentation, and thoughtful adoption of new tools and workflows. 

• 12–15+ years of related experience in product management, innovation, strategy, venture building, product discovery, or adjacent disciplines, including experience leading complex, high-impact product portfolios, product leaders, or transformational product programs. 

• Demonstrated strength in core product management craft with a spiked ability on customer discovery, product strategy, outcome definition, prioritization, experimentation, analytics, roadmap development, and lifecycle management. 

• Established experience leading early-stage discovery, incubation, Horizon 3 programs, 0-to-1 product development, or new business model exploration. 

• Experience translating strategic priorities and OKRs into product roadmaps, exploration portfolios, learning plans, and measurable outcomes. 

• Proven ability to facilitate senior-level cross-functional teams through ambiguity, tradeoffs, conflict, and decision-making. 

• Experience operating in regulated, complex, or enterprise environments where legal, risk, data, privacy, compliance, SOX, governance, and control considerations shape product discovery, experimentation, and delivery. 

• Strong fluency with AI-enabled product development, AI-assisted workflows, or AI-powered customer experiences, with a practical understanding of responsible experimentation and governance. 

• Excellent executive communication skills, including the ability to synthesize complex discovery work into concise narratives, recommendations, and decision points. 

• Strong commercial and analytical acumen, including experience with opportunity sizing, business case development, cost/benefit analysis, investment tradeoffs, KPI impact, and P&L implications. 

• Ability to attract, coach, and develop strong product talent while building a culture of curiosity, urgency, accountability, and learning. 

• Bachelor’s degree or equivalent experience required; MBA or advanced degree preferred. 

• Experience with product planning and delivery tools such as ADO, Aha, Atlassian, or equivalent. 

Leadership Mindset 

The ideal candidate is comfortable operating early in ambiguity, testing assumptions quickly, and changing direction when evidence suggests a better path. They know how to create structure without bureaucracy, inspire teams without over-resourcing, and use evidence to shape conviction. They are equally strong in product craft, people leadership, facilitation, commercial judgment, AI fluency, and enterprise influence. Most importantly, they can help H&R Block explore the future with discipline—finding the next growth opportunities while protecting focus, capital, team capacity, and enterprise trust.