Vice President, Enterprise Sales

Job Title:

Vice President, Enterprise Sales

Position Summary:

Penn Foster Group is seeking a Vice President, Enterprise Sales to build and scale our B2B sales engine from the ground up. While Penn Foster has a long-standing direct-to-consumer foundation, our employer and social impact partnerships business is in its early stages and poised for significant growth. This role will transform a largely reactive, inbound-driven motion into a structured, proactive, and scalable enterprise sales organization.

The Vice President will be responsible for designing the go-to-market strategy, building the sales infrastructure, and developing a high-performing team to drive predictable revenue growth. This is a highly visible, high-impact role focused on creating a repeatable enterprise sales motion and positioning Penn Foster as a strategic partner to employers (e.g. vet and healthcare organizations, retail, etc.) as well as social purpose organizations and workforce development partners (e.g. YouthBuild, JobCorps).

About the Team & Business:

Penn Foster’s Partnerships Team is responsible for driving B2B growth by partnering with employers, healthcare systems, and nonprofit and public sector organizations to deliver workforce education and training solutions. These partnerships help organizations build talent pipelines, upskill talent, improve retention, and expand access to career-aligned education.

Today, the B2B business operates like an early-stage startup within a scaled organization. Revenue is generated primarily through inbound and opportunistic partnerships, with limited formal structure around segmentation, pipeline management, or enterprise sales strategy. The current enterprise motion is transactional, with smaller deal sizes and shorter sales cycles, and significant opportunity exists to move toward larger, multi-stakeholder, consultative partnerships.

The team currently includes a small group of inside sales representatives, one account executive, and is in the process of adding enterprise sellers. This role will define the future structure, build the sales organization, and establish the processes and discipline required to scale into a predictable, enterprise-grade revenue engine.

Essential Job Functions:

• Build and scale Penn Foster’s enterprise sales function, transitioning from an inbound, opportunistic approach to a proactive, structured go-to-market model
• Define and operationalize ideal customer profiles (ICPs), segmentation strategy, and territory design
• Establish a consultative, enterprise sales motion focused on multi-stakeholder, solution-based selling
• Design and implement sales processes, pipeline management standards, and forecasting rigor in partnership with Revenue Operations
• Develop and execute a scalable pipeline generation strategy, including outbound motion and alignment with enterprise marketing
• Hire, lead, and develop a high-performing sales team, including Enterprise Sellers and inside sales representatives
• Assess current team structure and talent; retain, develop, or rebuild as needed to support future growth
• Partner with the Chief Commercial Officer to implement sales methodology and drive adoption across the team
• Build operating cadence, reporting, and performance metrics to drive accountability and visibility
• Lead the evolution of deal strategy from transactional sales toward larger, longer-cycle enterprise partnerships
• Collaborate cross-functionally with Marketing, RevOps, Product, and Customer Success to align go-to-market strategy and execution
• Foster a culture of accountability, continuous improvement, and mission alignment

Knowledge, Skills, Abilities:

• Proven experience building or transforming a B2B or enterprise sales function in an early-stage or scaling environment
• Strong operator mindset with the ability to design systems, processes, and infrastructure that enable predictable revenue growth
• Experience leading consultative, multi-stakeholder enterprise sales cycles
• Demonstrated success hiring, developing, and leading high-performing sales teams
• Deep understanding of pipeline management, forecasting, and sales performance metrics
• Ability to operate effectively in ambiguity and build structure in environments with limited existing processes
• Strong cross-functional leadership skills, with experience partnering closely with marketing and revenue operations
• Strategic thinker with the ability to translate vision into execution
• Clear and compelling communicator, capable of engaging stakeholders at all levels
• Mission alignment and passion for expanding access to education and workforce development opportunities

Requirements:

• 10+ years of experience in consultative B2B sales, partnerships, or related fields
• 5+ years of leadership experience, including building and developing sales teams
• Experience in early-stage, high-growth, or transformation environments
• Track record of owning and delivering against revenue targets
• Experience leading enterprise or complex sales environments preferred
• Background in education, workforce development, healthcare, or social impact sectors is a plus, but not required

Work Environment & Hiring Requirements

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.

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.