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.
As Dealerware’s customer base grows and our product evolves, Dealer Success is essential to keeping the focus on value. Our customers need more than account or relationship management. They need trusted advisors who know the product inside and out, understand what our customers are trying to accomplish, and can recommend the best way to get there.
Dealerware’s Dealer Success Manager (DSM) partners directly with a portfolio of dealerships aligned by OEM, consulting them on how to get the most value from Dealerware. This is a customer-facing role, primarily conducted by phone and Zoom with occasional visits to dealership locations, and it is responsible for protecting and growing revenue through Gross Revenue Retention (GRR) and Net Revenue Retention (NRR). The Dealer Success Manager reports to the Manager, Dealer Success.
As a Dealer Success Manager responsibilities:
Customer Consulting & Relationship Management
- Own Net Revenue Retention (NRR) for your portfolio: proactively identifying, pursuing, and closing expansion opportunities such as, products, and services, and partnering with Sales on execution where needed to grow the value each account delivers.
- Serve as a trusted, consultative advisor to a portfolio of dealerships aligned by OEM, helping them get the most value out of Dealerware.
- Bring a white-glove, highly responsive approach to dealer availability, exercising sound judgment on what warrants immediate attention.
- Build strong relationships with dealership staff across phone, Zoom, and in-person visits.
Business Reviews & Playbook Execution
- Proactively engage with dealerships by leading Impact Reviews (IRs) and Quarterly Business Reviews (QBRs) with dealerships in your portfolio. These cadences make up a significant part of the role.
- Follow established dealer success playbooks to guide dealers from onboarding handoff through renewal and expansion.
- Support OEM campaigns as they launch, helping dealers understand and act on them.
Metrics & Account Health
- Own GRR and NRR outcomes for your portfolio of dealerships.
- Monitor customer adoption, utilization, and overall health to proactively identify opportunities and potential risks to customer satisfaction and retention, developing mitigation plans as needed.
- Escalate customer concerns appropriately while coordinating internal resources to drive timely resolution.
- Maintain accurate customer account documentation, engagement plans, and success metrics.
- Own upsell outcomes within your portfolio by consulting dealers on how to maximize value across their account, including expansion into additional Dealerware products, and partnering with Sales as needed.
Growth & Development
- Bring a growth mindset: seek feedback, build new skills, and grow within the Customer Success organization.
- Actively participate in coaching and development opportunities provided by your manager.
- Understand SaaS metrics including GRR, NRR, and churn rate.
- Comfortable using AI-powered customer success tools to manage a portfolio efficiently.
- Outstanding phone and video communication skills, comfortable leading structured business reviews with dealership leadership.
- Strong judgment under pressure, able to triage customer needs and set expectations appropriately.
- Comfortable following established playbooks while bringing a consultative, problem-solving approach to each dealer conversation.
- 2+ years of customer-facing experience, preferably in B2B SaaS.
- Automotive or dealership experience is a plus.
- 10% travel to dealership locations, including occasional overnights, required.
- Competitive base salary with bonus incentive eligibility
- Full benefits (medical, dental, vision, disability)
- 401(k) with company match
- Tuition reimbursement and continuing education
- Unlimited paid vacation policy
Skills Required
- 2+ years of customer-facing experience
- B2B SaaS experience
- Automotive or dealership experience
- Ability to travel 10% to dealership locations, including occasional overnights
What the Team is Saying
Dealerware Compensation & Benefits Highlights
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Healthcare Strength — Benefits are described as comprehensive, with medical, dental, vision, and mental-health support alongside convenient telehealth options. Feedback suggests this breadth meaningfully enhances the overall value of the package.
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Leave & Time Off Breadth — Unlimited PTO is emphasized along with paid holidays and sick time. Feedback suggests this flexibility supports work-life balance and ease of time away.
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Parental & Family Support — Paid, gender‑neutral parental leave, family‑forming benefits, a return‑to‑work program, and onsite accommodations are highlighted. Feedback suggests these offerings stand out as particularly supportive for families.
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.
