Director, Customer Data and Insights

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, Customer Data and Insights is a strategic, operations-focused leader responsible for defining and executing the customer data strategy, analytics function, and operational platforms that enable data-driven decision-making across Penske’s Digital Fleet organization. Reporting to the VP of Customer Experience, this role owns the vision, governance, and optimization of customer data and CRM ecosystems, ensuring the business maintains a unified, accurate, and actionable 360-degree view of the customer journey. This includes integrating and leveraging data from website engagement, marketing interactions, product usage, post-sales activities, and customer requests to deliver insights that improve customer retention, operational efficiency, revenue growth, and overall business performance.

Serving as a critical partner across Customer Success, Sales, Marketing, Product, and Finance, the Director leads a team of data and business analysts and acts as the organization’s primary expert on customer data and CRM best practices. This role oversees the implementation, administration, and continuous enhancement of customer data and operational platforms, while establishing the analytics, reporting, and governance frameworks needed to identify opportunities, mitigate risk, and support strategic decision-making. As a key change agent, this leader transforms customer data into actionable insights, ensuring priorities are aligned with business objectives and enabling the organization to make informed decisions that drive sustainable growth and customer success.

As a newly established leadership role within a rapidly growing digital business, this position requires an entrepreneurial builder who can create the customer data and insights function from the ground up. The successful candidate will establish strategy, governance, operating model, reporting frameworks, and technology roadmap while providing hands-on leadership and delivering immediate business impact from day one.

Qualified candidates will bring 10+ years of experience in CRM administration, Revenue Operations, Customer Success Operations, or analytics—preferably within a SaaS environment—along with deep expertise in CRM configuration, administration, and workflow automation. This role also requires at least 5 years of leadership experience with a demonstrated ability to build, develop, and manage high-performing teams.

Major Responsibilities:

CRM Platform Ownership

• Lead end-to-end implementation, administration, and continuous optimization of HubSpot CRM

• Define pipeline structures, deal stages, contact properties, and lifecycle stages — built to scale

• Own requirements gathering, system configuration, UAT, and go-live

• Serve as the organization's primary SME on CRM best practices and platform capabilities

• Coordinate third-party vendors and implementation consultants; manage timelines and deliverables

Customer 360 & Data Strategy

• Own, develop, maintain and mature our enterprise-wide customer data strategy

• Build and maintain a complete 360-degree customer data model across the CRM and other Customer Data Platforms

• Integrate signals from website engagement, marketing activity, product usage, post-sales motions, and support data

• Translate business objectives into data strategies that drive retention, expansion, and operational efficiency

• Establish and enforce data governance standards — data integrity, compliance, and quality metrics

Analytics, Reporting & Insights

• Own the definition, tracking, and governance of core SaaS metrics: churn, retention, NRR, expansion, and health, etc.

• Design and maintain scalable dashboards and reporting frameworks for Sales, Product, CS, and Executive leadership

• Deliver a monthly SaaS reporting suite that includes narrative-driven interpretation — not just numbers, but what they mean

• Build and maintain a living reporting glossary: KPI definitions, business rules, and data definitions, reviewed quarterly

• Analyze pipeline, lead sources, conversion funnels, and behavioral signals indicating churn risk or expansion opportunity

• Partner with Revenue and Finance on forecasting and performance analysis

• Build cohorts and segments based on behavioral patterns; calculate cohort-based retention and revenue metrics

Cross-Functional Partnership

• Partner with CS, Sales, Marketing, Product, and Finance to standardize metrics and enable consistent enterprise-wide reporting

• Develop recommendations for CRM enhancements that increase team productivity and maximize revenue

• Analyze support ticket trends and customer friction points; provide insights on interventions

• Coordinate with Legal, Finance, and IT to ensure all reported metrics meet compliance and audit standards

• Enable data-driven decision making across the enterprise.

Team Leadership & Change Management

• Build, lead, and develop a high-performing team of data and business analysts

• Drive CRM adoption and data literacy across the organization — lead enablement, training, and change management

• Champion a culture of data-driven decision-making from the front lines to the executive suite

• Foster curiosity, accountability, and continuous improvement within the team

Other projects and tasks as assigned

Qualifications:

• Bachelor’s degree in business Analytics, Marketing, Data or Computer Science required

• Master’s degree in engineering, Data Science, Analytics, or Marketing preferred

• HubSpot CRM certification required at time of hire or within 90 days

• 10+ years of experience in CRM administration, revenue operations, customer success operations or analytics required – preferably in a SaaS environment

• 5+ years in people management or a leadership capacity required

• Demonstrated experience leading a CRM implementation from scoping through go-live

• Proven track record managing enterprise-scale platforms and analytics tools

• Experience in a multi-sided marketplace or complex B2B technology environment a plus

• Deep expertise in CRM configuration, administration & workflow automation required

• Advanced proficiency in SQL or data analytics and business intelligence tools (Tableau, Power BI, Looker) preferred

• Demonstrated experience building reporting infrastructure in modern data stacks such as Snowflake, dbt, or equivalent

• Familiarity with CRM integrations via APIs or middleware platforms

• Data Analytics or BI certifications (Tableau, Power BI, Google Analytics) a plus

• Proven ability to translate complex data into clear, actionable insights for executive stakeholders

• Strong business and financial acumen, including the ability to understand revenue and contract drivers, forecast retention and growth metrics, and continuously evaluate the ROI of customer programs and services.

• Strong cross-functional collaboration and influence skills — across Sales, Marketing, IT, and external partners

• Proven ability to lead, coach, and develop a team in a technology-heavy environment, with the ability to drive accountability and results through others

• Experience establishing data governance frameworks and ensuring data quality at scale

• Highly organized; capable of managing multiple critical projects simultaneously in a fast-paced environment

• Analytical mindset paired with emotional intelligence and a collaborative, adaptable communication style

• 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

About Penske Truck Leasing/Transportation Solutions

Penske Truck Leasing/Transportation Solutions is a premier global transportation provider that delivers essential and innovative transportation, logistics and technology services to help companies and people move forward. With headquarters in Reading, PA, Penske and its associates are driven by a dedication to excellence and a commitment to customer success. Visit Go Penske to learn more.

Job Category: Executive

Job Function: Marketing & Communications

Job Family: Marketing & Communications

Address: 100 Gundy Drive

Primary Location: US-PA-Reading

Employer: Penske Truck Leasing Co., L.P.

Req ID: 2610512