Customer Success Manager - Chicago

Location: Remote (Chicago, IL)

Type: Full-Time

Work Arrangement: Remote. You must live in the Chicago area, with regular travel to customer dealerships across the region.

About Flai

AI has transformed B2B SaaS, but has struggled to penetrate the real-world industries that shape our lives. Flai is building the leading AI-native communications platform for car dealerships.

A $1.3 trillion industry, auto dealerships sell 96% of the 16 million new cars sold each year. Yet they universally run on outdated systems and manual processes, which is why dealerships spend $36B each year on operations. That’s our opportunity.

We launched our first voice AI product a year ago. Since then, we have deployed multiple products across hundreds of dealerships across the U.S. We’ve partnered with the 2nd largest automaker in the country and many of the leading dealership groups. We’ve raised from leading VCs including First Round Capital, Toyota Ventures, Y Combinator, Innovation Endeavors, SV Angel, and Liquid 2.

We’ve grown insanely quickly with a small, scrappy team and continue to move at that pace.

Role Overview

We're hiring a Customer Success Manager to be the connective tissue between us and our customers, sitting right at the center of one of the fastest-moving stories in AI right now. Working shoulder to shoulder with a founding team that moves fast and never sits still, you'll get to onboard and scale accounts, drive real adoption and outcomes, and run the playbooks and processes that make Flai the standard for AI in this industry. You'll have a genuine voice in how the product evolves based on what you're seeing and hearing inside stores every day.

What You'll Do

Own onboarding and rollout: Lead the show from kickoff to go-live across single rooftops and groups, owning timelines, integrations, training, and launch day.

Drive adoption and outcomes: Get dealerships genuinely hooked on using Flai daily, and prove it with data, missed-call capture, appointment set rate, response time, show rate, retention.

Be the quarterback for your customers: Build real relationships with the people running these dealerships, GM, GSM, Fixed Ops Director, Service Manager, BDC Manager, and become the person they trust most.

Run the operating cadence: Set the rhythm with weekly check-ins, launch reviews, and QBRs, and keep everyone accountable to the metrics and the next moves.

Handle escalations like an operator: Be the calm, fast, trusted voice when something breaks, triaging issues and working hand in hand with product and engineering.

Follow the playbook, and help sharpen it: Execute Flai's onboarding, training, renewal, and support processes with real rigor, and get a direct hand in making them sharper as you learn what actually works.

Renew and expand: Own retention and growth across your accounts, multi-rooftop rollouts, new use cases, more volume, and be the one who spots the opportunity first.

Be the connective tissue to product: Get a front-row seat translating what's happening inside dealerships into real product feedback, spotting patterns and helping shape what we build next.

Must Have

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

Early-Stage Experience: Experience in a customer-facing role at an early-stage B2B SaaS company, you know what it takes to build trust with customers before a big brand name is doing the work for you.

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 follow process diligently and run a tight ship.

Customer Obsessed: You build real relationships with the people you work with and genuinely care about their outcomes, not just the account health score.

High Ownership: You take full accountability for your accounts and follow through relentlessly, nothing falls through the cracks on your watch.

Excited to Be Early: You want to be part of a company at its earliest, most electric stage, energized by that even while working inside an evolving process rather than building one from scratch.

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)

Why Flai

This is about as early as it gets: real traction, customers who genuinely love the product, and investors who've backed some of the best companies in the world betting big on us. You'll be living inside one of the most exciting build-outs in AI right now, in an industry that's about to look completely different because of what we're building. How you run a call, handle an escalation, or close a renewal in the next 12 months will directly shape how Flai serves customers for years to come. We move fast and we have fun doing it. Come be part of the story while it's still being written.

What We Offer

• $85K-$135K OTE depending on experience
• Equity
• Full benefits including medical, dental, and vision

Flexible PTO

A small, high-trust, fast-moving team that has a genuinely good time building something real