Customer Success Manager - Chicago

The role

The Customer Success Manager will onboard and scale accounts to drive adoption and outcomes. You will build relationships with dealership leadership and provide product feedback to shape future development.

What you will do

• Lead onboarding and rollout from kickoff to go-live
• Drive adoption and outcomes using data like missed-call capture and appointment set rate
• Build relationships with dealership GMs, GSMs, and managers
• Run the operating cadence with weekly check-ins, launch reviews, and QBRs
• Handle escalations by triaging issues with product and engineering
• Execute and sharpen onboarding, training, renewal, and support processes
• Own retention and growth across accounts and multi-rooftop rollouts
• Translate dealership activity into product feedback

Required qualifications

• Experience owning a book of business and driving adoption/retention in a fast-moving environment
• Experience in a customer-facing role at an early-stage B2B SaaS company
• Clear, confident, and organized communication
• Strong CRM hygiene, notes, tasks, and consistent account plans
• Ability to build real relationships and care about customer outcomes
• Full accountability for accounts
• Excitement to be part of a company at its earliest stage

Nice to have

• 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)

Benefits

• Equity
• Medical
• Dental
• Vision
• Flexible PTO

About the company

Flai is building an AI-native communications platform for car dealerships. The company has deployed products across hundreds of dealerships and is backed by investors including First Round Capital and Y Combinator.