Director, Customer Success - Digital Retail

The Role

The Director, Digital Retail Customer Success is responsible for executing the Customer Success strategy across the direct-to-dealer customer segment for our 700 Digital Retail dealer customers. This senior role ensures retailers achieve measurable business outcomes (sales, traffic, gross profit) and long-term value from our Digital Retail solutions, driving retention, expansion, and advocacy.

Impact You Will Have in This Role

In this role, the Director, Digital Retail Customer Success will have a significant impact on customer growth, retention, and long-term business success by ensuring our 700 Digital Retail dealer customers realize measurable value from our solutions. Through strategic leadership, cross-functional collaboration, and a strong customer-centric approach, this individual will drive adoption, improve customer outcomes such as sales, traffic, and profitability, and strengthen customer advocacy.

What You’ll Be Doing In This Role

• Help define the Customer Success strategy, frameworks, and processes to maximize retention, adoption, and expansion for Digital Retail dealer customers.
• Establish metrics and KPIs for customer health, engagement, and financial outcomes (e.g., GRR, NRR, expansion).
• Foster a culture of customer-centricity, operational discipline, and data-driven decision-making.
• Build executive relationships across dealer organizations to champion Digital Retail and act as a trusted advisor at the leadership level.
• Deliver measurable business outcomes, including adoption, lead generation, sales, ROI, and gross profit for participating dealers.
• Understand key metrics for individual dealers and align engagements accordingly.
• Serve as the Voice of the Customer internally, providing strategic insights to Product and Customer Solutions.
• Lead Executive Business Reviews (EBRs) and QBRs (or similar) for Dealer Groups.
• Partner with Sales to identify expansion opportunities and support account growth strategies.
• Identify at-risk accounts and proactively intervene to prevent downsell or churn.
• Own the strategic client impact on Gross Retention Rate (GRR), Net Revenue Retention (NRR), and expansion revenue for Digital Retail products.
• Support adoption of standardized processes, tools, and reporting for the Customer Success organization.
• Measure account health, risk, and opportunity.
• Establish realistic dealership KPI’s for Digital Retail that JDP can measure.
• People Leadership: Support a high-performance, customer-focused culture across the Customer Success team.

Qualifications Of This Role

• Bachelor’s degree preferred, not required
• 7-10 years of Digital dealership management experience with a strong Digital background
• 7+ years of progressive experience in Customer Success, Account Management, or Customer-Facing Leadership roles.
• 5+ years of experience leading high-performing Customer Success teams.
• Proven track record of driving retention, expansion, and adoption for enterprise B2B clients.
• Strong understanding of technology-enabled solutions, platforms, or SaaS products.
• Excellent executive presence, communication, and relationship management skills.
• Strong analytical skills with the ability to interpret usage, adoption, and financial metrics to inform strategy.