Director of Customer Success at Fastbreak AI

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 and over 65 leagues worldwide, and our platforms run some of the largest youth and amateur sports organizations across North America.

Fastbreak is intent on providing the best customer support in sports technology. Our youth sports customers, including leagues, clubs and tournament organizers, run live sports events where reliability makes a huge difference in the lives of participants and their families. There is no margin for error when a ticketing system is down and you can’t admit parents and fans into an event.

We are hiring a Director of Customer Success to own and scale our post-sale customer engine. This role is responsible for onboarding, customer support, retention, training, and account expansion. You will build the infrastructure, systems and workflows that turn customer experience into a predictable driver of customer satisfaction, account retention, and product expansion.

This is a player-coach role. You will operate inside 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 company's Chief Operating Officer and have the autonomy and independence to create stellar customer experiences.

Over time, you will scale this into a team that delivers consistent outcomes. week over week. This role does not carry a quota.

What You’ll Do

Build the Post-Sale Customer Engine

• Own the full post-sale lifecycle from onboarding through first use, 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 new customer kickoff through their 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

• You'll manage a growing team of 6 CS reps from day 1
• You'll own customer support as a core Fastbreak function
• 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

Requirements

You Are a Great Candidate If You

• Have a genuine love of sports
• Have experience managing youth sports at any level: org director, coach, administrator, team parent
• Take ownership of customer outcomes, especially when things break
• Build processes and systems that reduce reliance on heroics and scale your team's 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
• Are comfortable being on-call on weekends as you build out the team

Required

• 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

Preferred Experience

• 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

Location

• 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%

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.
• More about careers at Fastbreak AI.

If you're an 'A' player at the top of your game, please apply! This is an immediate opening.

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.