Director, Customer Success (Digital Products)

Penske•Cumru Township, PA

About The Position

Penske is a leader in the transportation and supply-chain industry with a 50-plus year history of delivering world-class technology solutions. The company is also a significant data company, collecting and analyzing billions of data points annually through advanced analytical models to provide customers with a comprehensive view of their supply chains. Penske is investing in and growing its digital products and is seeking talent to help advance the industry. The key to Penske's success is its people, who work on innovative projects and help develop technology solutions that drive the company and its customers forward.

Requirements

10+ years of experience in Customer Success, Account Management, Revenue Operations, or post-sales leadership within enterprise SaaS environments.
Proven track record of leading high-performing teams and driving customer outcomes through direct accountability for team performance.

Nice To Haves

Experience creating customer success organizations from the ground up and transforming them into mature, high-performing functions.

Responsibilities

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