Director of Customer Success

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.

• 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

• 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

• 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

• 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

• You love sports
• You take ownership of customer outcomes, especially when things break
• You build systems that reduce reliance on heroics and scale impact
• You think in terms of leverage and design workflows that incorporate AI from the start
• You understand how customer loyalty and customer support quality drive revenue
• You operate across functions and move between strategy and execution easily
• You are comfortable being on-call on weekends as you build out a team

• 7+ years in Customer Success, Account Management, Implementation, or Support
• 2+ years leading a customer success function
• Experience owning retention, NRR, or expansion revenue targets
• Proven track record in building or scaling a post-sale function, including lifecycle and expansion strategy
• Experience in high-pressure, real-time environments such as events, payments, or scheduling
• Strong partnership with Product and Engineering to influence roadmap decisions
• Excellent written communication across customer-facing and executive contexts
• Willingness to participate in an on-call rotation, including nights and weekends

• Experience with youth sports professionally or personally, or ticketing or event operations 
• Hands-on experience designing or deploying AI-powered customer experiences (knowledge bases, agents, automated lifecycle flows).
• Experience with multi-product environments
• Familiarity with scheduling systems or payment platforms

• This is an in-office position
• You’re based in (or are planning to relocate to) Charlotte, NC, and excited to work in person.
• Relocation assistance available
• Some travel is required. 5%

• Competitive base salary.
• Company stock options.

• Health, dental, and vision insurance to keep you covered.
• 401(k) with employer match.
• The opportunity to shape the future of a rapidly growing company that loves sports.
• More about careers at Fastbreak AI.

If this sounds like you, please apply! This is an immediate opening.

NOTE:

Applicants must be legally authorized to work in the USA. We are unable to sponsor or take over sponsorship of an employment visa at this time.

We are an equal-opportunity employer and value diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.