Fastbreak AI is a rapidly growing leader in sports operations software. Our products create the schedules of professional leagues like the NBA, MLS, and NHL as well as some of the largest youth and amateur sports organizations across the globe.
Our youth sports customers, including leagues, clubs and tournament operators, run live sports events where reliability is everything. There is no margin for error when you can’t admit parents and fans into an event.
We are hiring a Director of Customer Success to own and scale the post-sale customer engine. This role is responsible for onboarding, support, retention, and expansion revenue across all products. You will build the systems and workflows that turn customer experience into a predictable driver of retention, upgrades, and cross-sell.
This is a player-coach role. You will operate the function while building it. You may be defining a customer health model during the week and helping a support representative resolve a live event issue on the weekend. You'll report directly to the Chief Operating Officer and have the autonomy and independence to create a stellar customer experience.
Over time, you will scale this into a team that delivers consistent outcomes.week over week.
What You’ll Do
Build the Post-Sale Customer Engine
- Own the full post-sale lifecycle from onboarding through retention, renewal, and expansion
- Design and implement the systems, tooling, and AI-driven workflows that make delivery scalable
- Define customer health, usage signals, and risk indicators that drive proactive engagement
- Build structured motions for upgrades, cross-sell, and expansion tied directly to product usage
- Turn customer outcomes into revenue through renewals, upsell, and multi-product adoption
- Develop advocacy programs that generate referrals, case studies, and repeat business
Own Onboarding and Time to Value
- Lead onboarding from kickoff through first live event
- Reduce time-to-first-event and accelerate time-to-value across customer segments
- Partner with Sales to support late-stage deals and ensure clean, accountable handoffs
- Standardize onboarding into repeatable playbooks that scale
Lead Customer Support and Live Event Operations
- Own customer support as a core function, not a reactive layer
- Act as escalation owner for live event issues including scheduling, payments, and operations
- Build the on-call model, escalation paths, and incident response playbooks
- Ensure every issue is resolved, documented, and permanently addressed
- Define and maintain the standard for fast, clear, and effective customer communication
Drive Cross-Functional Execution
- Act as the voice of the customer with Product and Engineering
- Bring structured feedback that improves product decisions and release quality
- Own Help Center and self-service strategy to reduce support volume over time
- Partner with Sales and Finance to ensure accurate pricing and packaging
- Align closely with Sales and Marketing to convert expansion opportunities into revenue