Customer Success Manager - Chicago

🏢 Flai · 📍 Chicago · 💼 remote · ⏰ FullTime

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Position Summary & Responsibilities

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 Yet they universally run on outdated systems and manual processes, which is why dealerships spend $36B each year on operations.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 c

🎯 Candidate Preparation Guide For Flai Applicants

Key Role Competencies & Evaluation Highlights

Key Role Focus:

Evaluating advanced AI/ML capabilities, spatial data processing expertise, and the ability to turn complex computer vision into enterprise value.

📋 Preparation Priorities (Key Areas to Clarify):

1. Academic over-indexing on theoretical model architecture without considering real-world inference costs and latency.
2. Inability to explain complex AI outputs in simple terms to non-technical enterprise stakeholders.
3. Lack of hands-on experience handling messy, real-world sensor data.

✨ Recommended Role Alignment Hook:

I specialize in turning messy, real-world spatial data into high-performance, production-ready computer vision pipelines that enterprises can actually rely on.

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