Senior Director, Product Explorations

This is a fully remote position, open to applicants in Missouri.

📋 Description

• Lead Explorations and Discovery.

• Define and oversee learning agendas that clarify customer problems, target segments, unique value propositions, feasibility, desirability, viability, commercial potential, compliance considerations, and pathways to scale.

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

• Manage the transition from discovery to validated concepts, including executing experiments, providing executive recommendations, and developing clear transition plans to the relevant core product pillar when opportunities are ready for expanded delivery.

• Uphold a disciplined approach favoring small teams, rapid learning cycles, and evidence-based decision-making prior to significant investments.

• Construct and assess business cases for exploratory opportunities, encompassing market sizing, customer impact, cost/benefit analysis, investment needs, risks, and potential KPI or P&L impacts.

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

• Bring exceptional Product Craft and Coaching.

• Establish high standards for product management skills, which include customer discovery, problem framing, outcome definition, opportunity sizing, prioritization, experimentation, and storytelling.

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

• Lead, mentor, and cultivate product managers and product leaders, exemplifying strong product skills and fostering a high-performing Explorations team.

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

• Exhibit sound judgment in balancing exploration with focus, ensuring teams avoid premature scaling or overbuilding before significant signals are present.

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

• Advocate for discovery, experimentation, and AI-enabled product practices throughout the broader Product organization, helping define what "great" looks like in modern product management at H&R Block.

• Facilitate and Lead Cross-Functional Teams.

• Coordinate complex, cross-functional working sessions that unify diverse perspectives and guide teams toward clear decisions, next steps, and accountable parties.

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

• Lead through influence among senior stakeholders, fostering alignment without solely relying on reporting authority.

• Operate as an effective matrix leader and bridge builder, securing 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 clearly surfacing risks, tradeoffs, dependencies, and decision points in a timely manner.

• Ensure teams concentrate on the most valuable questions and avoid getting sidetracked into coordination-heavy activities without measurable learning.

• Advance AI Enablement and New Ways of Working.

• Identify and implement AI-driven methods to expedite discovery, research synthesis, prototyping, analysis, product documentation, and experimentation.

• Collaborate with technology, data, legal, risk, and enterprise AI enablement teams to ensure experiments and AI-enabled workflows function within suitable guardrails.

• Investigate product opportunities where AI agents, automation, and data-driven personalization can deliver differentiated value for clients, tax professionals, and associates.

• Act as a prominent product leader who exemplifies AI fluency, practical experimentation, and thoughtful adoption of new tools and workflows.

⛳️ Requirements

• 12-15+ years of relevant experience in product management, innovation, strategy, venture building, product discovery, or related fields.

• Proven expertise in core product management skills, particularly in 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 in converting strategic priorities and OKRs into product roadmaps, exploration portfolios, learning plans, and measurable outcomes.

• Demonstrated ability to guide senior-level cross-functional teams through ambiguity, tradeoffs, conflict, and decision-making processes.

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

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

• Excellent executive communication skills, including the capacity to distill complex discovery efforts into concise narratives, recommendations, and decision points.

• Robust commercial and analytical insights, including experience with opportunity sizing, business case development, cost/benefit analysis, investment tradeoffs, KPI impacts, and P&L considerations.

• Ability to attract, mentor, and develop strong product talent, fostering a culture of curiosity, urgency, accountability, and learning.

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

🏝️ Benefits

• Qualifying associates can enroll themselves and/or their eligible dependents in medical and prescription drug coverage.

• Can participate in the H&R Block Retirement Savings Plan (401(k) Plan).

• Employee Assistance Program.

• (Virtual) fitness center programs.

• Associate discount program.

• Automatically enrolled in Business Travel Accident Insurance.

• Receive Associate Tax Prep benefit.