Upper Hand Head of Product Strategy INDIANAPOLIS, IN · Full time

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Upper Hand is a vertical SaaS platform serving youth sports facilities and clubs across North America. We provide sports management software that helps facilities run their operations, from scheduling and registration to payments and facilities management. We're at an exciting inflection point - scaling our customer base while modernizing our technical infrastructure to support sustainable growth. For more information on how Upper Hand is reinventing the way business is done in youth sports, visit upperhand.com.

JOB SUMMARY

We’re looking for a Head of Product Strategy to help define the next chapter for Upper Hand. You’ll own product discovery and a long-term roadmap the whole company can rally around, drawing on market insight, product analytics, and regular conversations with the facility owners, staff, coaches, parents, and athletes who use our software. You’ll measure product usage and gather feedback to make sure product investments tie to outcomes that matter: adoption, retention, and satisfaction.

This is an exciting, transformational opportunity to drive where our product goes next. You’ll report directly to the COO and work as a peer to the Head of Product Delivery, who turns the roadmap into shipped, customer-ready software. You’ll own what we build and why, with Product Delivery owning how it gets built and getting it into the hands of our customers.

DUTIES AND RESPONSIBILITIES

Product Strategy and Roadmap

• Set the direction. Develop a long-term product strategy and multi-quarter roadmap organized around clear themes and outcomes, then rally the company and our customers around it.
• Frame the problem. Define each initiative with a clear brief covering the customer problem, supporting evidence, intended users, desired outcome, and how we’ll measure success.
• Own the prioritization framework. Maintain a clear prioritization framework used to rank roadmap initiatives, based on customer value, level of effort, and evidence.
• Know the market and what’s next. Track market trends, the competitive landscape, and customer segments, turning what you learn into strategy and sharing what you learn so the whole company sees where the market is heading.
• Drive pricing and packaging decisions. Determine how we group features into packages, tiers and add-ons that make sense for different customer segments, and recommend pricing and monetization models in partnership with the Head of Sales & Marketing, the COO, and the CEO.

Discovery and Customer Insights

• Lead discovery. Lead our discovery program, engaging business owners, facility staff, parents, and athletes to observe workflows, validate problems, and test ideas before we build. Involve the Head of Product Delivery in a meaningful number of these conversations so that both roles work from a common understanding of customer needs. Bring the Voice of the Customer into discussions and decisions involving other functional areas in the business.
• Measure outcomes. Define success metrics for each initiative and report on adoption, usage, and business impact after launch. Use product analytics to reveal what customers use and what they don’t, across new and existing features alike. Dig into why some features thrive while others go untouched. Feed what you learn back into the roadmap, deciding whether to invest further, simplify, or change direction.
• Turn feedback into insight. Review feature requests and roadmap-level feedback routed from Product Delivery's intake process, and close the loop with Sales, Support, and customers on what we will and won't build.
• Set UX direction. Set the high-level UX direction for roadmap initiatives, coordinating with our Heads of Product Delivery and Engineering to translate design themes into executable implementation.

Required Experience, Education, and Skills

• 5+ years of product management experience in B2B2C SaaS, including meaningful time at a lean software company (under 100 employees) where you rolled up your sleeves and found resourceful ways to get things done without a big company budget.
• Demonstrated ability to build a thematic, outcome-oriented, multi-quarter roadmap and a prioritization framework that others understand and trust.
• Demonstrated ability to connect product decisions to measurable improvements in adoption, retention, conversion, and expansion.
• Track record of defining product metrics and using data to drive decisions, including experience standing up analytics where they did not previously exist.
• Experience conducting customer discovery and turning qualitative and quantitative feedback into product direction.
• Experience driving pricing and packaging decisions.
• A strong instinct for usability, and the ability to make the case for investing in reliability, performance, and UX.
• Demonstrated experience using Claude or other similar AI tools for road mapping and prototyping.
• Although not required, it is a plus if you have experience with software serving youth sports organizations, or similar software markets such as fitness, children’s activities, or booking/scheduling platforms.
• Bachelor’s degree or equivalent practical experience.