Dealer Success Manager

Dealerware, Inc.; Ann Arbor (MI); On-site; USD 77,000 - 94,000; Full time

Benefits offered by this job

401(k) with company match

Tuition reimbursement

Unlimited paid vacation

Job summary

Dealerware, Inc. in Ann Arbor, MI is seeking a Dealer Success Manager to protect and grow revenue across a portfolio of dealerships. You will advise on product value, manage relationships, and drive expansion opportunities through Dealerware products.

You will own GRR/NRR, monitor usage and health, and partner with Sales on upsells while traveling to dealerships as needed.

Qualifications

• 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.

Responsibilities

• Own Net Revenue Retention (NRR) for your portfolio and identify expansion opportunities.
• Serve as a trusted advisor to dealerships aligned by OEM to maximize value from Dealerware.
• Provide a white-glove, responsive approach to dealer availability and urgent issues.
• Build strong relationships with dealership staff via phone, Zoom and in-person visits.
• Lead Impact Reviews and Quarterly Business Reviews with dealerships in your portfolio.
• Follow dealer success playbooks from onboarding to renewal and expansion.
• Support OEM campaigns, helping dealers understand and act on them.
• Own GRR and NRR outcomes; monitor adoption, health, and risks; mitigate as needed.
• Escalate concerns and coordinate internal resources for timely resolution.
• Maintain accurate account documentation and engagement plans.
• Drive upsell opportunities by advising on Dealerware products with Sales.

Skills

Customer-facing experience

B2B SaaS familiarity

Automotive or dealership experience

Job description

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.

Your peers would say you:

• 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.

Required qualifications:

• 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.

Dealerware offers you:

• Competitive base salary with bonus incentive eligibility
• 401(k) with company match
• Tuition reimbursement and continuing education
• Unlimited paid vacation policy

The pay range for this role is:

85,000 - 85,000 USD per year (Ann Arbor, MI)