Director of Customer Success

Fastbreak AI
Charlotte, NC

We're a fast-moving startup building software that powers tournaments and events for sports organizations across the country. Our customers run live, time-sensitive operations. Schedules need to be published on Friday, gates open Saturday morning, and there is no pause button. They need a partner who picks up the phone.


We are hiring a Director of Customer Success to build the customer-to-revenue engine that takes us from scrappy and heroic to scalable and predictable. You will own the full post-sale customer experience across our product lines including onboarding, adoption, retention, expansion, and the live-event safety net, and you'll design the systems, playbooks, and AI-powered workflows that let us deliver that experience at scale.


This is a player-coach role at a startup. On Monday you might be redesigning our customer health model and aligning Product on roadmap trade-offs; on Saturday you might be on the phone with a tournament director whose schedule won't publish. You should want both. Over the next 12 to 18 months you'll grow this from a function you operate yourself into a team you lead.


Responsibilities

  • Design and operationalize an end-to-end customer lifecycle system covering onboarding, adoption, health monitoring, expansion, and renewal
  • Build the AI-powered infrastructure that lets a small CS team punch above its weight: knowledge architecture, automated nudges, self-serve adoption flows, and intelligent escalation
  • Stand up the systems and tooling foundation including CS platform, ticketing, knowledge base, and customer comms, and make pragmatic build-vs-buy calls
  • Build the expansion motion by identifying upsell and cross-sell signals in product usage, designing the playbooks, and partnering with Sales and Marketing to convert them
  • Build the case-study, referral, and customer-advocacy programs that turn happy customers into a growth channel
  • Own onboarding strategy and execution from kickoff through first live event, with measurable improvements to time-to-first-event and time-to-value
  • Partner with Sales on late-stage deals and demos where customer success expertise influences the outcome, and own the handoff into onboarding
  • Serve as front-line responder and escalation owner for event-day issues including schedule publishing, payment failures, and gate-time problems, including evenings and weekends
  • Stand up the on-call rotation, escalation paths, and incident-response playbooks that protect customers without burning out the team
  • Partner with Product and Engineering as a peer, pressure-testing new releases against real customer scenarios before they ship and bringing structured, prioritized customer feedback into the roadmap
  • Own the Help Center and self-service strategy across product lines
  • Work weekly with Finance to track and reconcile billable activity and partner on pricing and packaging decisions that affect retention and expansion


Requirements

  • 7+ years in Customer Success, Account Management, or Implementation, with 2+ years leading a CS, onboarding, or implementation function
  • Direct experience owning and hitting an NRR or retention number for SMB and/or mid-market SaaS customers
  • Built or significantly scaled a Customer Success function at a startup or growth-stage SaaS company including playbooks, health model, lifecycle stages, and expansion motion
  • Proven comfort with high-pressure, real-time customer issues in event operations, payments, scheduling, or comparable live-ops environments
  • Track record of partnering effectively with Product and Engineering to influence the roadmap with structured customer insight
  • Strong written communication across formats including Help Center articles, customer-facing communications, post-incident summaries, and exec-level reporting
  • Availability on nights and weekends as needed and willingness to own the on-call rotation


Preferred

  • Background in sports tech, ticketing, event management, or live-operations software
  • Hands-on experience designing or deploying AI-powered customer experiences
  • Experience migrating customers across platforms
  • Hands-on experience with scheduling tools and payment processing 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.
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