Founding Customer Success Manager

Flai is an AI communications platform for auto dealerships. Dealers use Flai to capture every customer, eliminate friction, and automate communication outside the store so their teams can focus on closing deals and delivering exceptional in-person experiences.

Flai is backed by First Round Capital, Toyota Ventures, Y Combinator, SV Angel, Liquid 2 Ventures, Innovation Endeavors, and other world-class investors.

We’re hiring a Founding Customer Success Manager to own and build Flai’s customer success function from the ground up. You will onboard and scale dealership and dealer group accounts, drive adoption and outcomes, and help define the playbooks, metrics, and processes that become the Flai standard.

You’ll work directly with the founders and be a key voice in how the product evolves based on what’s happening inside stores.

Own onboarding and rollout — Lead implementations from kickoff to go-live across single rooftops and groups. Coordinate timelines, integrations, training, and launch checklists.

Drive adoption and outcomes — Ensure dealerships actually use Flai daily and see measurable impact (missed-call capture, appointment set rate, response time, show rate, retention, etc.).

Be the quarterback for the account — Build strong relationships with decision makers and day-to-day champions (GM, GSM, Fixed Ops Director, Service Manager, BDC Manager).

Run the operating cadence — Set up weekly check-ins, launch reviews, and QBRs. Create accountability around actions, metrics, and next steps.

Handle escalations like an operator — Triage issues fast, coordinate with product/engineering, communicate clearly, and keep trust high when something breaks.

Build the CS machine — Create repeatable playbooks for onboarding, training, renewals, expansion, and support handoffs. Help define what “good” looks like across a portfolio.

Renew and expand — Own retention and expansion motions (multi-rooftop rollouts, adding use cases, increasing volume). Identify growth opportunities and partner with sales when needed.

Close the product feedback loop — Translate dealership reality into crisp product feedback. Spot patterns, propose fixes, and help prioritize what matters most.

Proven Customer Success Execution — Experience owning a book of business and driving adoption/retention in a fast-moving environment.

Sharp Communication — Clear, confident, and organized with dealers. Strong at leading calls, training teams, and writing clean follow-ups.

Operational Discipline — Strong CRM hygiene, notes, tasks, and consistent account plans. You run a tight ship.

High Ownership — You don’t wait for instructions. You identify problems, propose solutions, and drive outcomes.

Comfort with ambiguity — You can build the plane while flying it. Founding role means process + execution at the same time.

• Experience with dealer tech ecosystems (DMS/CRM/schedulers, call tracking, BDC workflows)

• Experience scaling onboarding across multi-rooftop groups

• Comfort with light technical coordination (integrations, data mapping, troubleshooting)

• Experience with QBRs tied to dealership KPIs (RO count, appointments, CSI, retention)