Customer Success Manager

atFlaiRemoteUS flagIllinoisFull-timeCustomer SuccessMid-levelSenior$85k – $135k/year

Posted Oct 5

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Lead the onboarding process for customers and manage the rollout from kickoff to go-live across individual rooftops and dealership groups.

• Oversee timelines, integrations, training, and the launch day activities.

• Promote dealership adoption and track measurable outcomes, such as missed-call capture, appointment set rates, response times, show rates, and retention rates.

• Cultivate relationships with dealership leaders, including General Managers, General Sales Managers, Fixed Operations Directors, Service Managers, and BDC Managers.

• Conduct weekly check-ins, launch reviews, and quarterly business assessments.

• Address escalations and work collaboratively with product and engineering teams to resolve issues.

• Implement and enhance onboarding, training, renewal, and support processes.

• Manage account retention and growth through multi-rooftop rollouts, new use cases, and increased volumes.

• Convert dealership feedback into product insights to influence future development.


⛳️ Requirements

• Must reside in the Chicago area.

• Willingness to travel regularly to customer dealerships throughout the region.

• Proven experience managing a book of business and driving adoption and retention in a dynamic environment.

• Background in a customer-facing role at an early-stage B2B SaaS organization.

• Excellent communication skills, demonstrating clarity, confidence, and organization when interacting with dealers.

• Proficient in leading calls, training teams, and producing clear follow-up communications.

• Strong adherence to CRM hygiene, including notes, tasks, and consistent account planning.

• Ability to meticulously follow processes and maintain organization.

• Familiarity with dealer tech ecosystems, such as DMS/CRM/schedulers, call tracking, and BDC workflows is advantageous.

• Experience in scaling onboarding processes across multi-rooftop groups is a plus.

• Comfort with light technical coordination, including integrations, data mapping, and troubleshooting, is beneficial.

• Experience with Quarterly Business Reviews (QBRs) linked to dealership KPIs is a plus.


🏝️ Benefits

• Equity.

• Comprehensive benefits package including medical, dental, and vision coverage.

• Flexible paid time off (PTO).

• Join a small, high-trust, and fast-moving team.

• Enjoy a genuine and fun work environment while contributing to building something meaningful.

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