Founder in Training Program – AI Track

and the job listing Expires on January 4, 2026

If you are a graduating senior with a passion for entrepreneurship, sports, and AI product strategy, Playbook would like to invite you to apply for our selective rotational Founder In Training Program!

Over 18 months you’ll work directly under our CEO, CTO, Director of AI, Director of Customer Success, and Director of Marketing. You’ll be instrumental in shaping a new paradigm in how organized sports, community recreation, and youth activities can be managed and serviced. At the end of 18 months, you’ll be promoted to a key role in the company that aligns with your strengths, interests, and career goals.

The program is designed for those who want to build the world of AI in sports. You’ll be exposed to all aspects of Playbook’s current and future strategic initiatives during an exciting and formative period. You’ll be given significant responsibility on an accelerated basis and you’ll be working with talented, likeminded individuals within an amazing, sports obsessed culture.

We are looking for people who have:

• A deep passion for creative uses of AI to solve real world problems
• Elite problem solving capacity
• The ability to shape projects and manage teams working on multiple projects at once
• A Bias for Action and a “get things done” mentality

– We have built the leading suite of AI agents in sports business management, with more and more tools being rapidly released constantly. You will be involved in every aspect of designing and implementing our AI strategy from day one, driving both the technical roadmap and business outcomes as we extend the platform’s capabilities into new areas of client operations.

– You will learn through doing. In this position, you will have the opportunity to unlock new levels of business avenues through Growth Hacking, with the freedom to experiment boldly and test unconventional strategies to reach new market segments.

– You will help design and execute models that redefine what it means to start and operate a community business. You’ll work closely with local business owners, gathering real-world insights and translating that feedback into actionable direction for our CEO and product team to shape the next generation of our platform.

– As a part of your role you will be on multiple meetings per week with the CEO. Within our transparent culture, you will gain exposure to all parts of the business. You will also be working closely with small business owners and learn a tremendous amount from these relationships.
If your ultimate goal is to start a business one day
, this role is for you.

– We have a flat, meritocratic culture. Your insights and ideas will have the potential to shape the company from the moment you arrive. There is no bureaucracy, politics, or blockers to your growth here. We have a track record of rapidly promoting exceptionally talented individuals.

– We are generous with equity options and we are taking off like a rocket ship towards our mission of building Shopify for sports and community organizations.

– If you love sports, you’ll love our culture. We have an incredible group of people that love sports here and sports are an instrumental part of our culture. Sportscasters and games are on in the office all day. We have monthly outings to VIP experiences at NBA, NFL, NHL, and MLS games.

This is not a typical entry-level role — it’s a chance to help architect the future of sports, community, and AI from the inside out. At Playbook, you’ll have the freedom to experiment, the support to grow, and the platform to leave your mark on a rapidly scaling company. If you’re driven by impact, innovation, and a love of competition, we can’t wait to meet you.