Director, Customer Success (Digital Products)

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 serve as the voice of the customer across the organization
• Build and manage customer segmentation, engagement models, and success motions.

Post-Sales Motion & Revenue Accountability
• Own the full post-sales customer lifecycle: onboarding, adoption, value realization, renewal, upsell, and cross-sell
• Drive and be accountable for Net Revenue Retention (NRR), Gross Revenue Retention (GRR), and Expansion Revenue targets
• Directly manage a portfolio of key enterprise accounts in the near-term, transitioning coverage as the team scales
• Identify and execute upsell and cross-sell opportunities across the existing customer base

Customer Retention & Growth
• Drive customer adoption, utilization, satisfaction, retention, and renewal performance
• Develop strategies to reduce churn and increase customer lifetime value
• Identify opportunities for account expansion, upsell, and cross-sell 
• Lead key customer relationships and support strategic account planning
• Oversee customer health scoring, risk identification, and intervention strategies

Team Leadership & Development
• Recruit, build, lead, and develop a high-performing team of Customer Success Managers, Onboarding Specialists, and Support professionals
• Establish clear expectations, performance standards, and career development paths for every role on the team
• Coach the team on enterprise relationship management, value-based conversations, and proactive risk identification
• Drive accountability through structured engagement cadences: team standups, pipeline reviews, health reviews, 1:1s, etc.
• Manage team capacity, workload planning, and organizational design as the company scales
• Foster an environment that supports and reinforces our culture

Cross-Functional Partnership
• Act as the primary voice of the customer internally by translating customer feedback, friction points, and feature requests into actionable input for Product and Engineering
• Partner closely with Sales to ensure seamless handoffs at close-won and collaborative engagement on expansion opportunities
• Work with Marketing to develop customer advocacy programs, case studies, and reference networks
• Align with Leadership and Finance on renewal forecasting, revenue recognition considerations, and pipeline reporting
• Coordinate with Support to identify systemic product issues, recurring service failures, and opportunities to reduce ticket volume through better onboarding and enablement

Playbook & Process Development
• Create onboarding frameworks, health scoring models, escalation protocols, Partnership Reviews, and renewal workflows
• Define customer segmentation strategy and coverage models aligned to account size, complexity, and revenue potential*
• Develop and maintain a living CS playbook that are regularly reviewed, continuously improved, and operationally enforced
• Establish customer success milestones, adoption benchmarks, and time-to-value standards for each customer segment
• Partner with the Customer data & Ops team to define the customer health metrics, signals, and thresholds that drive proactive intervention

Customer Journey & Program Management
• Design and optimize onboarding, implementation, adoption, renewal, and advocacy programs 
• Standardize customer engagement processes, playbooks, and success methodologies
• Ensure consistent delivery of customer experiences across all customer segments
• Develop scalable approaches for high-touch, hybrid, and digital customer engagement

Customer Experience & Escalation Management
• Serve as the executive escalation point for at-risk accounts and high-severity customer issues
• Lead partnership reviews with strategic accounts by delivering insights, demonstrating value, and reinforcing partnership
• Develop a proactive churn risk framework: identify early warning signals, assign intervention owners, and track resolution
• Champion a customer experience that reflects the complexity and operational stakes of fleet management and operation environments

Operational Excellence
• Monitor customer success KPIs and business metrics
• Analyze customer health, adoption, retention, and revenue trends to identify opportunities and risks
• Oversee the team’s usage of Customer Success technology platforms, CRM, and ensure good data hygiene and integrity practices are used consistently
• Leverage executive dashboards and reporting to communicate business performance and customer outcomes

Other projects and tasks as assigned.

Qualifications:
• Bachelor’s degree in business, Marketing, Communications, or related field required
• Master's Degree, MBA, or equivalent business discipline preferred
• HubSpot CRM Certification required at time of hire or within 90 days of hire
• 10+ years in Customer Success, Account Management, Customer Experience, or post-sales leadership, preferably in enterprise SaaS environments
• 10+ years of people management or customer success leadership capacity with direct accountability for team performance
• Demonstrated experience building or rebuilding a CS function, 0-to-1 experience is a meaningful differentiator
• Proven track record owning and improving NRR, renewal rates, and expansion revenue in a quota-bearing or equivalent accountability structure
• Experience developing and scaling customer success programs and processes
• Strong analytical, operational, and problem-solving capabilities
• Excellent communication, presentation, and executive relationship management skills
• Experience managing complex, technical B2B customer relationships at the enterprise level
• Bonus: Background in Telematics, Fleet Management, Transportation, Logistics, industrial SaaS, or operational technology environments
• Strong command of CRM platforms (HubSpot preferred) pipeline management, customer health tracking, and lifecycle workflows
• Comfortable with data: can read dashboards, interpret trends, and translate metrics into team action without needing an analyst at every turn
• Experience developing onboarding programs for technically complex products
• Ability to work fluidly in modern SaaS operating environments
• Proven ability to operate simultaneously as a strategist and a hands-on operator, especially in early-stage or high-growth environments
• Strong executive presence: credible, clear, and compelling in front of C-suite stakeholders and large enterprise customers
• Exceptional cross-functional collaboration and organizational influence without relying on formal authority
• Highly organized with the ability to manage multiple accounts, initiatives, and team priorities without dropping the ball
• Emotionally intelligent; knows how to read the room in a tense escalation and how to build lasting trust with demanding customers
• Demonstrated ability to translate customer insights into actionable priorities and drive alignment across Product, Sales, Marketing, and other cross-functional teams.
• Regular, predictable, full attendance is an essential function of the job.
• Successful candidate must complete Penske employment application, submit to a background investigation (past employment, education, and criminal history), and complete a drug screening.

Physical Requirements:
The physical and mental demands described here are representative of those that must be met by an associate to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. 
• The associate will be required to: read; communicate verbally and/or in written form; remember and analyze certain information; and remember and understand certain instructions or guidelines. 
• While performing the duties of this job, the associate may be required to stand, walk, and sit. The associate is frequently required to use hands to touch, handle, and feel, and to reach with hands and arms. The associate must be able to occasionally lift and/or move up to 25lbs/12kg. 
• Specific vision abilities required by this job include close vision, distance vision, peripheral vision, depth perception and the ability to adjust focus.
Penske is an Equal Opportunity Employer