Kaylee Williams hosts Natalie Merrill, COO and CFO of Bound, a high school athletics scheduling and ticketing platform experiencing remarkable growth. In just one year, Bound expanded from 600 to nearly 1,200 schools across the Midwest and beyond, nearly tripling its user base. The company is now launching its Series A funding round, marking a pivotal moment in its trajectory.
Natalie brings deep expertise to her dual role, having spent her career navigating different scales of business. She previously built a renewable energy company that went public, experienced a decade as a public company executive, and was acquired by Chevron in 2022 before joining Bound eight months ago. She shares critical lessons on managing cash flow at scale—emphasizing the importance of accurate forecasting, understanding revenue seasonality, and distinguishing between cash flow and income statement metrics. For Bound, this discipline has been essential to confidently approaching Series A while maintaining operational stability.
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The conversation explores what makes Bound beloved by customers: intuitive scheduling software for athletic directors, a redesigned family-centric app experience, and a team of 17 former athletic directors embedded in sales, support, and customer success roles. This human-centered approach, Natalie argues, is irreplaceable by AI—though the company strategically uses AI to enhance rather than replace human expertise.
Natalie addresses the role of AI in her own work, noting that tools like Claude have compressed financial modeling from weeks to hours. She also discusses the correlation between athletic participation and executive success, crediting the grit and resilience developed through sports as invaluable in startups.
As the episode concludes, Natalie reflects on the highs of hitting Bound’s 1,000-school milestone and the mission-driven culture that fuels the team. She offers founders practical wisdom: done is better than perfect, balance risk-taking with protection, and recognize that great leadership doesn’t require being the star player. With Series A on the horizon, Bound is positioned for its next phase of growth under strong operational leadership.