Director of Customer Success

Fastbreak AI • Charlotte, NC

3d • Onsite

About The Position

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.

Requirements

• 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
• Love sports genuinely, not just as a talking point
• Take ownership of customer outcomes, especially when things break
• Build systems that reduce reliance on heroics and scale impact
• Think in terms of leverage and designs workflows that incorporate AI from the start
• Understand how customer loyalty and support quality drive revenue
• Operate across functions and moves between strategy and execution easily
• Comfortable being on-call on weekends as you build out the team

Nice To Haves

• 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

Responsibilities

• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed