Playbook Sports

Act as CEO's extension to solve high-leverage problems across product, operations, AI, and internal systems in a fast-paced startup environment. | Looking for a highly motivated, ownership-driven individual with startup hustle and the ability to thrive in ambiguity, ideally with some scrappy project or startup experience. | This role works directly with our CEO, Josh Marcus, and is designed for someone who wants to build their own company one day. About Playbook Playbook Sports is building the operating system for sports businesses — the Shopify for sports. We power 500+ sports facilities, leagues, and clubs across the US & Canada with modern software and AI to help them grow, automate, and scale. We’re early, moving fast, and building something big. The Role This is not a traditional Chief of Staff role. You’ll act as an extension of the CEO, dropped into the hardest, highest-leverage problems across the company including product, ops, go-to-market, AI initiatives, and internal systems. You’ll see how a real startup is built from the inside: • How decisions actually get made • What matters vs. what doesn’t • How to turn chaos into execution You’ll be in the office 5 days/week in Hoboken, working side-by-side with leadership. No remote. No spectators. Who This Is For We do not care about degrees. We do care about hustle, judgment, and rate of learning. This role is for people who: • Want to be a founder someday • Thrive in ambiguity and move fast without instructions • Take ownership and hate loose ends • Would rather figure it out than ask for permission Bonus points if you’ve: • Started a company, side project, or anything scrappy • Worked at a Seed or Series A startup • Been the “go-to” person when things broke What You’ll Do • Work directly with the CEO on strategy and execution • Turn half-formed ideas into shipped outcomes • Own cross-functional projects with real business impact • Identify bottlenecks and eliminate them • Build internal processes, systems, and operating rhythm • Support product discovery, customer research, and delivery • Help scale the company without adding unnecessary complexity If something is important and doesn’t have a clear owner, it will probably be yours. Why This Role Is Special • Extreme proximity to the CEO and decision-making • Unmatched exposure to building a company from zero → scale • Real responsibility from day one • A proven culture of promoting high performers internally This role is intentionally a launchpad. Many people in seats like this go on to become founders, early executives, or product leaders. If this is your dream role, I'd love to hear from you personally at josh.marcus@callplaybook.com.

Act as CEO's extension to solve high-leverage problems across product, operations, and AI initiatives in a fast-moving startup environment. | Seeking a self-driven, ownership-taking individual with startup hustle and judgment, ideally with scrappy project experience and a desire to found a company. | This role works directly with our CEO, Josh Marcus, and is designed for someone who wants to build their own company one day. About Playbook Playbook Sports is building the operating system for sports businesses — the Shopify for sports. We power 500+ sports facilities, leagues, and clubs across the US & Canada with modern software and AI to help them grow, automate, and scale. We’re early, moving fast, and building something big. The Role This is not a traditional Chief of Staff role. You’ll act as an extension of the CEO, dropped into the hardest, highest-leverage problems across the company including product, ops, go-to-market, AI initiatives, and internal systems. You’ll see how a real startup is built from the inside: • How decisions actually get made • What matters vs. what doesn’t • How to turn chaos into execution You’ll be in the office 5 days/week in Hoboken, working side-by-side with leadership. No remote. No spectators. Who This Is For We do not care about degrees. We do care about hustle, judgment, and rate of learning. This role is for people who: • Want to be a founder someday • Thrive in ambiguity and move fast without instructions • Take ownership and hate loose ends • Would rather figure it out than ask for permission Bonus points if you’ve: • Started a company, side project, or anything scrappy • Worked at a Seed or Series A startup • Been the “go-to” person when things broke What You’ll Do • Work directly with the CEO on strategy and execution • Turn half-formed ideas into shipped outcomes • Own cross-functional projects with real business impact • Identify bottlenecks and eliminate them • Build internal processes, systems, and operating rhythm • Support product discovery, customer research, and delivery • Help scale the company without adding unnecessary complexity If something is important and doesn’t have a clear owner, it will probably be yours. Why This Role Is Special • Extreme proximity to the CEO and decision-making • Unmatched exposure to building a company from zero → scale • Real responsibility from day one • A proven culture of promoting high performers internally This role is intentionally a launchpad. Many people in seats like this go on to become founders, early executives, or product leaders. If this is your dream role, I'd love to hear from you personally at josh.marcus@callplaybook.com.