Director of Customer Success

Fastbreak AI•Charlotte, NC

1d•Onsite

About The Position

Fastbreak AI is seeking a Director of Customer Success to lead and scale its post-sale customer operations. This role is crucial for managing the entire customer lifecycle, including onboarding, support, retention, and expansion revenue across all products. The successful candidate will be responsible for developing systems and workflows that leverage customer experience as a key driver of retention, upgrades, and cross-selling. This is a player-coach position where the individual will both operate the function and build it out, potentially defining customer health models and assisting with live event support. The role reports directly to the Chief Operating Officer and offers significant autonomy. The long-term goal is to build a team that consistently achieves desired outcomes.

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

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 systems, tooling, and AI-driven workflows for scalable delivery.
Define customer health, usage signals, and risk indicators to drive proactive engagement.
Build structured motions for upgrades, cross-sell, and expansion tied to product usage.
Drive revenue through renewals, upsell, and multi-product adoption by focusing on customer outcomes.
Develop advocacy programs to generate referrals, case studies, and repeat business.
Own Onboarding and Time to Value: Lead onboarding from kickoff through the 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 handoffs.
Standardize onboarding into repeatable, scalable playbooks.
Lead Customer Support and Live Event Operations: Own customer support as a core 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 all issues are resolved, documented, and permanently addressed.
Define and maintain standards for fast, clear, and effective customer communication.
Drive Cross-Functional Execution: Act as the voice of the customer with Product and Engineering.
Provide structured feedback to improve product decisions and release quality.
Own Help Center and self-service strategy to reduce support volume.
Partner with Sales and Finance to ensure accurate pricing and packaging.
Align closely with Sales and Marketing to convert expansion opportunities into revenue.