Overview

Why Join Digital Products at Penske Most people know Penske for our big yellow trucks. But we're so much more than that. At Penske we have a 50-plus year history of leading the transportation and supply-chain industry, delivering world-class and award-winning technology solutions. What most people don't know, we are just as much a data company as we are a transportation and supply chain company. We collect and analyze billions of datapoints each year, through over 300+ advanced analytical models and integrate insights from our fleet, maintenance operations, and logistics networks to give customers a more complete view of their supply chains. That connected intelligence allows us to anticipate issues, optimize resources, and deliver reliable outcomes across transportation and logistics for our customers. Penske continues to invest in, and grow, our digital products - and we need talent at all levels to help us advance and continue to lead our industry. While data is very important, the key to our success is our people. You'll work alongside great people and on really cool projects. Ultimately, you'll help develop and ensure our technology solutions keep our company and our customers moving forward. Position Summary: The Director of Customer Success is a strategic and hands-on leader responsible for the overall success, retention, and growth of Digital Fleet customers throughout the entire post-sales lifecycle. Reporting to the VP, Customer Experience / Chief Customer Officer, this role owns customer onboarding, adoption, value realization, retention, renewals, expansion, and long-term customer health. As the leader of Customer Success, Onboarding, and Support, the Director is accountable for key business outcomes including Net Revenue Retention, Gross Revenue Retention, Customer Lifetime Value, Time to Value, and customer satisfaction. This role develops and scales the strategies, processes, and customer engagement frameworks that ensure customers achieve measurable business outcomes while maximizing the value of their Digital Fleet investment. Given the growth stage of the product, this leader must be a hands-on builder who can lead out of the gates, balancing direct customer engagement with the development of scalable processes, infrastructure, and team capabilities. The ideal candidate brings experience creating customer success organizations from the ground up and transforming them into mature, high-performing functions. The Director of Customer Success serves as a critical cross-functional partner to Sales, Product, Marketing, Operations, Finance, and Support, ensuring customer feedback and business insights drive organizational decisions and product innovation. As a player-coach and builder, this leader will initially manage key enterprise accounts while designing and implementing the infrastructure, playbooks, and team capabilities required to support long-term growth. By creating a customer-centric culture and establishing scalable success programs, the Director ensures customer outcomes are consistently delivered, demonstrated, and measured, driving customer advocacy, revenue retention, and expansion as the Digital Fleet business continues to scale. Qualified candidates will bring 10+ years of experience in Customer Success, Account Management, Revenue Operations, or post-sales leadership within enterprise SaaS environments, along with a proven track record of leading high-performing teams and driving customer outcomes through direct accountability for team performance. Major Responsibilities: Customer Success Strategy & Leadership - Co-develop and execute the Customer Success strategy aligned with company growth objectives - Establish and scale customer success programs, processes, and customer lifecycle frameworks - Create a culture centered on customer outcomes, ownership, accountability, curiosity, continuous improvement, operational excellence, and customer obsession - Ensure the Customer Experience organization s