Customer Success Manager

About Dealerware 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, a core value of Diversity, Equity & Inclusion, and a leadership and management team that defaults to being supportive and accessible. 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. The current role opening will manage the following region: Midwest (including Canada). Frequent, same-day travel to client sites is an essential function of this position. For this reason, the candidate must reside within the assigned region. See specific states per region on the application page. Additional travel includes occasional overnight stays within the territory, periodic trips to Austin, TX headquarters, and air travel up to 20%. Key Responsibilities Adoption & 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. Account Management & Relationship Building 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. Training & Optimization 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. Collaboration & Continuous Improvement 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. Required Qualifications 3+ years in customer success, account management, or a related customer-facing role in an automotive software company. 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. Additional travel includes occasional overnight stays within the territory, periodic trips to Austin, TX headquarters, and air travel up to 20% Dealerware Offers You Competitive base salary range of $65,000–$85,000 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 Dealerware is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or expression (including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances. Dealerware's management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities, access to facilities and programs and general treatment during employment. *We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.