Chief of Staff to the CEO
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 — 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.