[Remote] Head of Revenue Operations

Note: The job is a remote job and is open to candidates in USA. Penn Foster Group is seeking a Head of Revenue Operations to build and lead its enterprise commercial operating model across B2B and B2B2C revenue motions. The role owns GTM strategy execution, systems, data, analytics, forecasting, and operational processes to drive accountable revenue performance and scale.

Responsibilities

• 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
• 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
• 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
• 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
• 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

Skills

• 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
• 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
• 10+ years of progressive leadership in Revenue Operations, Commercial/Sales Operations, or GTM strategy, including experience leading the function in a multi-segment business
• 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
• 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
• Experience operating in a private-equity-backed, transformation, turnaround, or post-acquisition environment is preferred
• 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
• Tableau or comparable business-intelligence experience is a plus
• MBA or other advanced degree welcomed

Benefits

• Medical, dental, and vision coverage
• Flexible spending
• Generous paid time off
• Sponsored volunteer opportunities
• 401(k) with a company match
• Free access to all of our online programs
• Remote position

Company Overview