Head of Revenue Operations

Company Overview
At Penn Foster Group, we are transforming online learning and creating accelerated paths to greater economic mobility. We equip learners with the real-world skills and knowledge they need 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 to coal miners seeking the skills needed for safer jobs. Today, together with the partners who use our education and training programs, we continue that mission by providing accessible education and training for in-demand skills and building a workforce prepared for the future job market.
The Opportunity
Penn Foster Group is at an inflection point in the evolution of its commercial engine. With a storied history, a portfolio of trusted education brands, a differentiated model spanning direct-to-learner and employer-partner channels, and private-equity sponsorship behind an ambitious growth agenda, the Company is investing in the operating infrastructure required to scale with discipline.
The Head of Revenue Operations will be a principal architect of that infrastructure and a visible commercial leader in Penn Foster’s next chapter.
This is a rare opportunity to build a true enterprise Revenue Operations (RevOps) function, with a clear seat at the commercial leadership table and ownership of the operating system that governs how Penn Foster plans, sells, enrolls, serves, and grows. The mandate combines strategy and execution: partnering in the development of the commercial operating model across the Company’s employer-partner (B2B) and direct-to-learner through our partners (B2B2C) motions; modernizing the go-to-market (GTM) data and technology foundation; and establishing the analytics, cadence, and governance required to drive predictable, accountable revenue performance at scale.
Position Summary
Penn Foster Group is seeking a Head of Revenue Operations to architect and lead the commercial operating model underpinning a growing, private-equity-backed, multi-segment education and workforce-training business. Reporting to the Chief Commercial Officer (CCO) and partnering closely with the Partnerships Leadership Team and Penn Foster’s Extended Leadership Team, this leader will own the systems, data, and processes that turn GTM strategy into enrollment, productivity, retention, and expansion.
This is a commercial leadership role, not a sales-support function. The successful candidate will serve as the CCO’s strategic advisor and the principal architect of Penn Foster’s go-to-market operating system. In partnership with Sales, Marketing, and Learner Success leadership, this person will help shape GTM strategy and independently own its translation into measurable, accountable revenue outcomes across both B2B and B2B2C.
The role’s scope spans four areas, unified under a single function:

Revenue Strategy & Planning

Marketing Operations

GTM Systems & Data

Sales Analytics & Insights

The role carries a clear transformation mandate: unify historically distributed commercial-support activities into a modern RevOps function, modernize the underlying technology and data stack, and establish the operating cadence required to scale the revenue engine. Success will depend on close partnership with Sales, Marketing, Learner Success and program delivery, Finance, IT, and HR.
Key Responsibilities
Revenue Operations Leadership

Serve as the CCO’s strategic advisor and chief of staff for commercial performance, partnering with the Partnerships Leadership Team. Architect the commercial operating model—including structure, governance, cadence, and decision rights—to connect strategy with execution across Sales, Marketing, and Success.

Build, scale, and lead a unified Revenue Operations organization. Set the standard for rigor, accountability, and scalability, and lead the cultural shift toward data-driven, forward-looking revenue management.

GTM Strategy, Planning, and Forecasting

Partner with the CCO, VP Sales, and commercial leaders to shape GTM strategy—including segmentation, coverage, and resource allocation—across B2B and B2B2C. Own the operational infrastructure that turns that strategy into a working revenue lifecycle, from demand through enrollment, retention, and expansion.

Lead the annual GTM planning process, including segmentation, coverage, capacity modeling, and growth-target setting, in partnership with Finance. Partner with the VP Sales on territory and quota design, applying the rigor needed to defend allocations to leadership and the Board.

Own forecasting and pipeline discipline, including cadence, methodology, accuracy standards, and committed, upside, and best-case rigor.

Establish governance forums—including business reviews, deal reviews, pipeline councils, and forecast calls—to keep the commercial organization aligned and accountable.

Analytics, Insight, and Performance

Own commercial analytics as a strategic capability, from Board-level reporting to front-line manager tools. Shift the function from descriptive reporting to predictive and prescriptive insight, including leading indicators, scenario modeling, win/loss analysis, and learner and partner health.

Establish enterprise data governance, including KPI definitions, a single source of truth, data quality, and asset ownership. Define and track seller and enrollment productivity—including revenue per rep, ramp time, selling time, and quota attainment—as a shared metric with Sales and Enrollment leadership. Equip leaders with a single, trusted view of commercial performance.

Sales Enablement and Productivity

Support the CCO and VP Sales’ enablement strategy as a measured function, assessing adoption, ramp, productivity, and revenue impact rather than relying on an event calendar. Build modern onboarding and continuous-development programs that reduce ramp time and improve mid-tenure productivity across sellers, managers, and enrollment/advisory roles.

Lead enterprise-wide standardization of opportunity management, deal and enrollment qualification, pipeline review, and sales methodology. Reduce the process, system, and handoff friction that constrains commercial velocity.

GTM Technology

Own the GTM technology and data roadmap, including CRM, marketing automation, sales engagement, conversation intelligence, enablement, and the data infrastructure that connects them.

Partner with the CCO, Partnerships Leadership Team, Finance, and HR on incentive design and administration to ensure incentives are paid accurately, motivate the right behaviors, and scale with the business.

Candidate Profile
The successful candidate will be a builder who has created or transformed RevOps capabilities in an environment where processes, systems, data, and team structures were still developing. They combine strategic judgment with operating rigor, are equally credible with a CCO discussing GTM strategy and a CFO discussing forecast confidence, and have the analytical horsepower to underwrite the numbers themselves.
This person has led a meaningful transformation, such as unifying a distributed RevOps function, modernizing a GTM technology and data stack, or installing the operating cadence needed to scale a commercial engine. They are fluent in the modern revenue-technology stack, have a point of view on how those tools change the work, and understand the difference between standardization that scales the business and standardization that suffocates it. Experience operating across both B2B and B2B2C revenue motions is highly valued.
They bring executive presence, narrative clarity, and the influence to lead through peers. They thrive in a fast-paced, mission-driven, private-equity-backed environment and build discipline without bureaucracy.
Preferred Experience and Qualifications

10+ years of progressive leadership in Revenue Operations, Commercial/Sales Operations, or GTM strategy, including experience leading the function in a multi-segment business.

Experience operating in a private-equity-backed, transformation, turnaround, or post-acquisition environment is preferred.

Track record of building or transforming a RevOps function—including its charter, team, operating model, technology, and data—in a complex organization.

Deep experience across the full revenue lifecycle, including GTM planning, forecasting, pipeline, deal execution, productivity, retention/renewal, and analytics.

Modern technology fluency, including comprehensive Salesforce experience and familiarity with the broader GTM stack: marketing automation, sales engagement, conversation intelligence, enablement, and business intelligence. Track record of using technology and automation to drive productivity.

Strong analytical skills and sales-forecasting experience, with the ability to define, articulate, and measure key GTM metrics across Sales, Marketing, and Customer/Learner Success. Strong Excel skills required; Tableau or comparable business-intelligence experience is a plus.

Experience across both B2B (employer, institutional, or channel) and B2B2C revenue motions preferred. Experience in education, services, or subscription businesses, as well as private-equity portfolio experience, is a plus.

Executive presence and the influence skills to lead through peers across Sales, Marketing, Success, Finance, HR, and Technology.

Ability to prepare clear, concise performance narratives and materials for executive leadership, private-equity sponsors, and the Board.

Highly proactive and self-directed, with the ability to anticipate commercial leaders’ needs, identify emerging issues, and independently develop the analysis, process improvements, and cross-functional actions required to address them.

Demonstrated ability to manage multiple concurrent deliverables and stakeholders with sound planning and resource-management discipline.

Bachelor’s degree required; MBA or other advanced degree welcomed.

Working Conditions & Hiring Process

U.S. Work Location Requirement: All employees must reside and perform work within the United States. International remote work arrangements are not supported for this role.

Travel Expectations: This is a remote position, though occasional travel may be required for team meetings, company events, conferences, summits, and similar activities. Candidates must be willing and able to travel as needed.

On-Camera Work Environment: Penn Foster Group operates in a highly collaborative, remote, on-camera culture. Employees are expected to be on camera during meetings unless extenuating circumstances apply.

Recorded Video Interviews: 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. These may include verification of employment history, education, and criminal background, where permitted by law.

Identity Verification (Form I-9): As part of the 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.

About Us: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.
Equal Employment Opportunity: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.
What We Offer:
We offer a robust benefits package that includes medical, dental, vision, flexible spending, generous paid time off, sponsored volunteer opportunities, a 401K with a company match, plus free access to all of our online programs.