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.

About Upper Hand

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 and 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.

Description

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.