Head of Product Strategy

Shape the future of Upper Hand’s youth sports software by leading product discovery, setting our long-term roadmap, and turning customer insights into measurable results. This is an exciting, transformational opportunity to drive where our product goes next.

We’re looking for a Head of Product Strategy to lead product discovery and define Upper Hand’s long-term product direction. You’ll combine customer conversations, market research, and product analytics to determine which problems we should solve, why they matter, and how we’ll measure success.

This is a hands-on role. You’ll spend time with facility owners, staff, coaches, parents, and athletes; test ideas; evaluate product usage; and translate what you learn into a clear, prioritized roadmap. Your work will connect product investments to improvements in adoption, retention, and customer satisfaction.

You’ll report directly to the COO and work as a peer to the Head of Product Delivery. You’ll lead product strategy, discovery, and roadmap prioritization; the Head of Product Delivery will lead execution and delivery of customer-ready software. Together with Engineering, you’ll maintain a shared understanding of customer needs and connect long-term direction with day-to-day product decisions.

Location: Remote. You should be able and willing to work Eastern Time business hours and travel occasionally to our Indianapolis office.

What You’ll Own

Customer Discovery and Market Insight

• Lead an ongoing discovery program with business owners, facility staff, coaches, parents, and athletes. Observe workflows, validate problems, and test ideas before we build.
• Involve the Head of Product Delivery in discovery conversations to develop a shared understanding of customer needs.
• Know the market and what's next: study market trends, the competitive landscape, and customer segments. Translate your findings into product opportunities and share them across the company.
• Synthesize feature requests and roadmap feedback from Product Delivery’s intake process. Communicate decisions and their rationale to Sales, Support, and customers.
• Bring customer perspectives into decisions across the business.

Product Strategy and Roadmap

• Set the direction: develop a long-term product strategy and multi-quarter roadmap organized around clear themes and measurable outcomes, then rally the company and our customers around it.
• Own the prioritization framework: establish and maintain a transparent prioritization framework that weighs customer value, business impact, supporting evidence, and level of effort.
• Frame the problem: define each initiative through a clear brief covering the customer problem, intended users, supporting evidence, desired outcome, and how we'll measure success.
• Set UX direction: set the high-level UX direction for roadmap initiatives, partnering with Product Delivery and Engineering to translate that direction into practical solutions.

Product Analytics and Outcomes

• Define success metrics for product initiatives and report on adoption, usage, and business impact after launch.
• Establish product analytics: understand how customers engage with both new and existing features, including why some features gain traction while others go unused.
• Turn feedback into insight and action: combine usage data with customer feedback to recommend where we should invest further, simplify the experience, or change direction.

Pricing and Packaging

• Drive pricing and packaging decisions: define feature packages, tiers, and add-ons that meet the needs of different customer segments, and recommend pricing and monetization models in collaboration with the Head of Sales & Marketing, COO, and CEO.

What You’ll Bring

• At least five years of product management experience in B2B2C SaaS, including meaningful experience at a software company with fewer than 100 employees. You’re comfortable doing the work yourself and making progress with limited resources.
• Experience leading customer discovery and translating qualitative and quantitative findings into product direction.
• Demonstrated ability to build a thematic, outcome-oriented, multi-quarter roadmap and a prioritization framework that others understand and trust.
• A track record of defining product metrics and using data to guide decisions, including establishing analytics where they did not previously exist.
• Demonstrated ability to connect product decisions to measurable improvements in adoption, retention, conversion, and expansion.
• Experience driving pricing and packaging decisions.
• A deep appreciation for usability and the ability to make the case for investments in reliability, performance, and user experience.
• Experience using Claude or similar AI tools for roadmap development and prototyping.
• A bachelor’s degree or equivalent practical experience.

Helpful Additional Experience

Experience with software serving youth sports organizations or related markets, such as fitness, children’s activities, or booking and scheduling platforms.