Resume

Wiltshire Ventures · Indianapolis, IN

• Lead a venture and operating platform investing at the intersection of small business, sports, and super intelligence, and build proprietary SI-enabled tools that help small and lower-middle-market businesses compete in an SI-first economy.
• Advise founders and operating executives on product, go-to-market, capital strategy, and CEO operating cadence, drawing on a 14-year founder and CEO playbook.
• Set investment thesis, source and evaluate deals, and lead diligence across SaaS, SI-native tools, and sports-adjacent small business categories.

Upper Hand (acquired by H3 Partners, 2026) · Chairman of the Board 2018-2021 · Consultant Nov 2025 - Mar 2026

• Founded and scaled the leading sports business management SaaS platform from a closet office in Maryland to category leadership and acquisition by H3 Partners in January 2026.
• Served 1,000+ small business owners across the sports industry. The platform processed $1B+ in customer revenue and powered experiences for 1M+ consumer end users.
• Drove 21%+ growth through COVID-19 and reached profitability while many peers shuttered, positioning the business for an institutional exit.
• Pivoted the bookacoach.com marketplace into Upper Hand SaaS and Upper Hand AI, capturing leadership in the youth sports vertical and expanding into adjacent small business markets.
• Raised multiple rounds of venture and strategic capital from Park Ten Capital and other institutional investors. Managed cap table, board, and shareholder relationships across 14 years.
• Built and led a senior leadership team across product, engineering, sales, customer success, and operations, and recruited the executive bench that drove the company through exit.
• Authored a public open letter to Indiana state and federal leaders in 2024 advocating balanced, ethical AI policy, initiating a state-level dialogue on AI governance.

Techstars Sports Accelerator · Indianapolis, IN

• Mentored five cohorts of sports technology founders on product strategy, go-to-market, fundraising, and CEO operating cadence.

Collect Rx, Inc. · Rockville, MD

• Owned a $10M+ book across 350+ hospitals and ambulatory surgery centers, consistently delivering 102%+ of national quota and reporting directly to the CEO.

ClassWatch LLC · Washington, D.C.

• Co-founded a venture-backed e-commerce company. Raised $1.15M and grew pre-money valuation from $0 to roughly $3M in 18 months across 18 authorized brand partners and 200+ collegiate licensees.

Corporate Executive Board, now Gartner · Chicago, IL

• Exceeded quota at 125%+ monthly attainment and ranked top 50 nationally leading Research and Technology Executive Council territory coverage.