Dealerware transforms the automotive retailers of today into the mobility network of tomorrow. Launched in 2016, Dealerware manages tens of thousands of vehicles at dealerships in North America across every major manufacturer brand. Dealerware is committed to being a people-first culture and a great place to work for all, with flexible scheduling, unlimited PTO, extensive benefits, and a leadership team that defaults to being supportive and accessible. Dealerware was recently backed by growth investors Wavecrest Growth Partners and Radian Capital and is entering an accelerated phase of growth and product expansion. In 2026, Dealerware was recognized by Built In as one of their Best Startups to Work for in Austin for the fifth consecutive year.
We are looking for an experienced and customer-focused Customer Success Manager (CSM) to join our team. This role combines the technical expertise of onboarding and training with strategic relationship management to drive customer adoption, satisfaction, and retention. The CSM will work closely with customers to ensure maximum product utilization and support long-term business outcomes.
This is a remote role based in Ann Arbor, Michigan or Indianapolis, Indiana. The role will manage the Midwest region: Michigan, Ohio, Indiana, Kentucky, Tennessee, North Carolina + Canada. Frequent, same-day travel (at least 50%) to client sites is an essential function of this position. Additional travel includes occasional overnight stays within the territory, periodic trips to Austin, TX headquarters, and air travel throughout the territory up to 20%.
Key ResponsibilitiesAdoption & Customer Success Strategies- Develop and execute customer success strategies to increase adoption and drive dealer engagement to meet business objectives.
- Proactively monitor customer usage and identify opportunities for improved utilization of platform features.
- Deliver monthly Executive Business Reviews and Impact Reviews, partnering with customer stakeholders to evaluate progress against success criteria, surface risk, and drive outcomes.
- Partner with customers to align platform use with their business goals and uncover growth opportunities.
- Act as the primary point of contact for assigned accounts, building strong, long-term relationships with key stakeholders.
- Provide ongoing support and guidance to customers, ensuring their satisfaction and loyalty.
- Proactively identify upsell opportunities, introduce new features, and ensure customer renewals.
- Handle escalations with professionalism and a focus on swift resolution.
- Manage occasional training, ensuring a smooth and timely implementation process for new users.
- Work cross-functionally to maintain implementation plans, including detailed timelines, milestones, and deliverables.
- Serve as a liaison between sales and implementation during the onboarding process, addressing customer needs and technical requirements.
- Act as the Voice of the Customer, sharing customer insights and feedback with internal teams to drive product and process improvements.
- Collaborate cross-functionally with Sales, Product, and Support teams to ensure customers achieve desired outcomes.
- Develop and contribute to scalable resources, including training materials, playbooks, and success templates.
- Stay informed on industry trends, best practices, and customer success innovations to enhance your impact.
- 3+ years in customer success, account management, or a related customer-facing role in a Saas software company.
- Experience in the automotive industry.
- Strong project management skills with a proven ability to manage multiple customers and priorities simultaneously.
- Exceptional communication and interpersonal skills, with a customer-centric approach to problem-solving.
- Proficiency in Salesforce and Jira, with an ability to analyze data and translate insights into action.
- A collaborative mindset and a passion for driving customer success and outcomes.
- Ability to travel up to 50%, including overnight travel.
- Competitive base salary with bonus incentive eligibility
- Full benefits (medical, dental, vision, disability)
- 401(k) with company match
- On-demand educational courses via LinkedIn Learning
- Tuition reimbursement and continuing education
- Unlimited paid vacation policy
- Flexible work
- Generous Paid Parental Leave program
- Modern office and a dynamic team in downtown Austin with free parking
- Friendly, small company environment with a progressive culture
Skills Required
- 3+ years in customer success, account management, or related customer-facing role in a SaaS company
- Experience in the automotive industry
- Strong project management skills with ability to manage multiple customers and priorities
- Exceptional communication and interpersonal skills with a customer-centric approach
- Proficiency in Salesforce and Jira and ability to analyze data and translate insights into action
- Ability to travel up to 50%, including frequent same-day travel and occasional overnight travel
- Collaborative mindset and passion for driving customer success and outcomes
What the Team is Saying
Dealerware Compensation & Benefits Highlights
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Leave & Time Off Breadth — Unlimited PTO with paid holidays and sick time is prominently offered, paired with flexible/hybrid scheduling. This breadth of leave is positioned as a core pillar of work-life balance.
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Parental & Family Support — Gender-neutral paid parental leave, a structured return-to-work program, an onsite Mother’s Room, and family-forming benefits via Carrot are explicitly provided. These elements indicate strong support through key family stages.
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Healthcare Strength — Comprehensive medical, dental, and vision coverage is paired with mental-health support including free, unlimited therapy visits. Disability, life insurance, and FSA options further bolster the health and protection stack.
Dealerware Insights
What We Do
Dealerware transforms the automotive retailers of today into the mobility network of tomorrow. Launched in 2016, Dealerware manages tens of thousands of vehicles at dealerships in North America across every major manufacturer brand. By combining a mobile-first approach with fresh design thinking, Dealerware’s industry-leading SaaS platform enables best-in-class fleet management and mobility services for the top automotive dealerships and manufacturers.
Why Work With Us
“I can't speak highly enough of my teammates. We do a great job of hiring curious, smart, dedicated, passionate and friendly people. This is our superpower.” This is a real comment from our engagement survey about our greatest asset and the best reason to work here: our team.
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Dealerware Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
To support operational effectiveness, team collaboration, and company culture, we require all hybrid employees to work onsite in the Austin, TX office at least two days per week on Tuesdays and Thursdays.
