Director of Customer Success

Fastbreak AI; Charlotte (NC); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Stock options

Health insurance

Dental & Vision insurance

401(k) with employer match

Relocation assistance

In-office role

Job summary

Fastbreak AI is hiring a Director of Customer Success to own and scale the post-sale customer engine across onboarding, support, retention and expansion. This leader will build the systems and workflows that drive consistent outcomes and revenue growth, including an on-call support model for live events.

The role reports to the Chief Operating Officer and will grow into a team responsible for delivering reliable, high-value customer experiences in fast-paced sports operations software.

Qualifications

• 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.

Responsibilities

• Build the Post-Sale Customer Engine from onboarding through retention, renewal, and expansion.
• Design AI-driven workflows and systems to scale delivery.
• Define customer health, usage signals, and risk indicators for proactive engagement.
• Create structured motions for upgrades and cross-sell tied 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 and standardize repeatable playbooks.

Skills

Customer Success

Account Management

Implementation

Support

Leadership

On-call

Tools

CRM systems

Help Center

Ticketing system

Job description

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

Requirements

You Are a Great Candidate If

• 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

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

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.