Head of Client Success

Head Of Client Success

Penn Foster Group is seeking a transformational Head of Client Success to build and scale a modern, strategic client success organization. This leader will evolve the function from a highly transactional, reactive support model into a proactive, outcomes-driven partnership organization focused on measurable customer outcomes, long-term retention, and account growth. Reporting directly to the Chief Commercial Officer, the Head of Client Success will define the vision, operating model, segmentation strategy, and customer engagement approach needed to support a rapidly growing partnerships business. This role will play a critical part in improving partner outcomes, increasing learner success and completion rates, strengthening cross-functional alignment, and creating predictable recurring revenue growth. The ideal candidate is a builder and change leader who thrives in ambiguity, enjoys creating structure from the ground up, and can balance strategic vision with operational execution in a mission-driven, high-growth environment.

Penn Foster's Partnerships business is in a period of significant evolution and growth, supporting employer, healthcare, veteran, and public sector organizations ranging from small accounts to complex enterprise partnerships exceeding $1M in annual revenue. Today, the Client Success organization has built strong relationship foundations with partners and serves as a key point of contact for customer support and engagement. As the business continues to scale, there is a substantial opportunity to transform the function into a more strategic, consultative, and outcomes-oriented organization. The current Client Success team consists of approximately 7 Client Success Managers, with additional growth planned, as well as a Client Coordinator support function that partners closely with the team to support both partner and learner operational needs. The organization is seeking to implement greater structure, segmentation, accountability, and proactive customer engagement while improving learner outcomes, partner satisfaction, retention, and expansion opportunities. This role will define the future operating model for Client Success and help establish Penn Foster as a best-in-class strategic partner to its customers through a high-touch, outcomes-driven customer experience.

• Establish and operationalize the long-term vision for the Client Success function
• Define what "great" looks like across the end-to-end customer lifecycle, from onboarding through renewal and expansion
• Build a scalable, outcomes-driven client success playbook focused on customer value realization, learner outcomes, retention, and growth
• Create infrastructure, processes, and operating rhythms that improve predictability across customer health, renewals, and expansion
• Design and implement customer segmentation and tiered service models based on account size, complexity, and growth opportunity
• Define engagement strategies, support models, and customer success expectations across segments
• Establish a proactive, consultative customer engagement approach rooted in measurable business outcomes
• Elevate the overall partner experience through responsive service, strategic partnership, and operational excellence
• Evolve the organization from reactive account management to strategic partnership management
• Build frameworks for account planning, customer health monitoring, executive engagement, and expansion opportunity identification
• Support Client Success Managers in developing multi-threaded relationships across partner organizations
• Partner closely with Sales to improve account handoffs, clarify ownership across expansion opportunities, and support long-term account growth
• Lead, coach, and develop a team of Client Success Managers and Client Coordinators
• Assess current team capabilities and organizational structure to support future scale and complexity
• Establish clear performance expectations, accountability measures, and development pathways
• Foster a culture of ownership, urgency, collaboration, continuous improvement, and customer advocacy
• Recruit and develop additional talent as needed to support business growth
• Partner closely with Revenue Operations to define reporting, customer health metrics, forecasting inputs, and performance dashboards
• Build consistent operating cadences including account reviews, business reviews, and renewal planning
• Clarify workflows and partnership models between Client Success and operational support teams to improve scalability and reduce reactive work
• Collaborate cross-functionally with Sales, Operations, Product, Academics, Marketing, and Revenue Operations to improve the end-to-end customer experience
• Create actionable feedback loops that inform operational, product, and customer experience improvements

• Proven ability to build or transform Client Success, Customer Success, Account Management, or strategic partnership functions in high-growth or evolving environments
• Strong strategic and operational mindset with the ability to create scalable systems, processes, and team structures
• Experience managing complex customer relationships and multi-stakeholder enterprise accounts
• Demonstrated success driving retention, expansion, customer engagement, and measurable customer outcomes
• Deep understanding of customer lifecycle management, segmentation strategies, and customer health methodologies
• Ability to lead through ambiguity and drive organizational change effectively
• Strong coaching, people leadership, and talent development capabilities
• Excellent cross-functional collaboration and stakeholder management skills
• Strong communication, influence, and executive presence
• Ability to balance strategic thinking with hands-on execution
• Data-driven mindset with the ability to use metrics and insights to drive decision-making and continuous improvement
• Passion for education, workforce development, social impact, or mission-driven work

• 10+ years of experience in Client Success, Customer Success, Account Management, Partnerships, or related customer-facing leadership roles
• 5+ years of leadership experience managing and developing teams
• Experience building or transforming customer-facing functions in high-growth, evolving, or ambiguous environments
• Proven track record improving retention, expansion, and customer outcomes
• Experience creating scalable operational processes, customer engagement models, and organizational structures
• Experience partnering closely with Sales, Operations, Product, and Revenue Operations teams
• Strong experience managing enterprise or complex customer relationships preferred
• Experience in education, workforce development, healthcare, veteran services, or social impact sectors is preferred but not required

• U.S. Work Location Requirement: All employees must reside in and perform work within the United States. We do not support international remote work arrangements for this role.
• Travel Expectations: While this is a remote position, occasional travel may be required for team meetings, company events, conferences, summits, etc. Candidates must be willing and able to travel as needed.
• On-Camera Work Environment: We operate in a highly collaborative, remote, on-camera culture. Employees are expected to be on camera during meetings unless extenuating circumstances apply.
• Recorded Video Interviews: All video interviews conducted during the hiring process will be recorded to support internal hiring consistency and process improvement.
• Background Checks: Employment with Penn Foster Group is contingent upon successfully completing applicable pre-employment screening requirements, which may include verification of employment history, education, and criminal background, where permitted by law.
• Identity Verification (Form I-9): As part of our onboarding process, all hires must complete employment eligibility verification in compliance with federal law. This includes remote Form I-9 verification, which may require an in-person identity verification step with an authorized representative.

At Penn Foster Group, we are transforming online learning to help learners by uniting Penn Foster, CareerStep, Ashworth College, James Madison High School, the New York Institute of Photography, the New York Institute of Art and Design, and other education platforms. Together, we create an accelerated path to greater economic mobility through real-world skills and knowledge that enable them to achieve long-term success in the workplaces of the future. Our history dates back to 1890 when our founder, Thomas Foster, pioneered distance education by offering training by mail for coal miners to get the necessary skills for safer jobs. Today, with the partners who use our education and training programs, we continue that mission of providing accessible training and education for in-demand skills and are building a workforce that's prepared for the future job market.

We strive toward Diversity, Equity, and Inclusion at Penn Foster Group by intentionally building teams that are diverse – in identities, lived experiences, and ideas to create a culture where people feel connected to each other and have a sense of belonging. We value diversity, equity, and inclusion because it is the foundation that enables us to achieve what we set out to do as an organization – from maximizing the number of learners who can reach their goals while giving them the kinds of experiences we want them to have, to becoming the type of company we want to work in.

We offer a robust benefits package that includes medical, dental, vision, flexible spending, generous paid time off, sponsored volunteer opportunities, a 401K with a