Source Job

$85,000–$135,000/yr
US Unlimited PTO

  • Own onboarding and rollout, leading from kickoff to go-live across single rooftops and groups.
  • Drive adoption and outcomes, using data like missed-call capture and appointment set rate to prove success.
  • Run the operating cadence with weekly check-ins, launch reviews, and QBRs, and handle escalations as a calm, trusted voice.

Customer Success B2B SaaS Communication CRM Onboarding

8 jobs similar to Customer Success Manager - Chicago

Jobs ranked by similarity.

US Unlimited PTO

  • Own expansion revenue across your book of customers and grow every account.
  • Expand Flai to more locations within existing dealer groups and launch new products.
  • Run the full deal cycle from demo to close while partnering with customer success.

Flai is building an AI-native communications platform for car dealerships, targeting a $1.3 trillion industry that runs on outdated systems. The company has grown quickly with a small, scrappy team and is backed by leading VCs like Y Combinator and Toyota Ventures.

US Unlimited PTO

  • Own the full sales cycle for new dealership customers, from first conversation to signed deal.
  • Run demos that show dealers exactly what Flai will do for their store, backed by real results.
  • Prospect on top of booked meetings to keep your calendar full and build pipeline.

Flai is building the leading AI-native communications platform for car dealerships. We've grown insanely quickly with a small, scrappy team and continue to move at that pace.

$90,000–$115,000/yr
US Unlimited PTO

  • Own onboarding and rollout across dealerships and multi-rooftop groups, coordinating integrations, training, and launch.
  • Drive adoption by connecting product usage to measurable dealership outcomes and building trusted leadership relationships.
  • Manage risk, run check-ins, and identify retention and expansion opportunities.

AgentDynamics builds AI agents for automotive retail, integrating with CRM and DMS platforms to automate sales and service workflows. We've expanded from a single dealership to multi-rooftop dealer groups in under a year, with a high-ownership culture and significant autonomy.

US

  • Own the customer's renewal, usage, and adoption of Kenect product features.
  • Identify, strategize and execute account expansions, feature upsells and cross-sales.
  • Deliver group and individual user informational and training sessions about Kenect features.

Kenect is a leading AI-powered texting and reputation management platform used by 10,000+ dealerships and service businesses across North America. They are a fast-growing, mission-driven team building technology that strengthens human connection in a digital-first world.

  • Own the full sales cycle for Flai's voice AI products across WA and OR, from prospecting to close.
  • Meet dealership leaders in person, build trust, manage pipeline, and shape go-to-market strategy.
  • Work with founders to influence product direction and win the dealership market with a founder mindset.

Flai is building an AI-native communications platform for automotive dealerships, transforming how they operate with voice AI products. Backed by major investors, we are a small, scrappy team that has grown rapidly and continues to operate with speed and ambition.

Australia 24w maternity 4w paternity

  • Manage a portfolio of 300 automotive dealer customers, building trusted relationships digitally.
  • Use data insights to improve product adoption, retention, and customer satisfaction.
  • Collaborate with sales and onboarding teams to deliver a seamless customer experience.

Carsales is an online vehicle marketplace that makes buying and selling cars a great experience. They have a large, evolving team with a collaborative culture, recognized as a Best Workplace in Australia.

$90,000–$100,000/yr
North America

  • Manage a portfolio of dealer accounts, driving software utilization and measurable ROI.
  • Build strong relationships with dealership stakeholders and conduct strategic needs assessments.
  • Identify at-risk clients and develop action plans to retain and grow revenue through upsells.

AutoFi provides digital commerce technology that powers sales and finance experiences for automotive brands and dealers. Backed by major investors and funded for growth, its diverse team across the U.S. and Canada is empathetic, gritty, curious, and humble.

$60,000–$68,000/yr
US

  • Support client adoption and satisfaction by delivering foundational product guidance and basic training.
  • Document client interactions and escalate routine blockers to senior team members as needed.
  • Maintain a learning plan to expand knowledge of CDK products and dealership workflows.

CDK Global is a leading provider of cloud-based software to dealerships and OEMs across automotive and related industries. The company fosters an inclusive culture that values curiosity, ownership, openness, and creating possibilities.