Director, Sales — Enterprise Healthcare at Penn Foster… · Location…

Director, Sales — Enterprise Healthcare

Penn Foster Group is a portfolio of online education and training solutions focused on creating accessible pathways into in-demand careers. We help learners build real-world skills and knowledge that support long-term success in the workplace.

We are seeking a Director, Sales — Enterprise Healthcare to build and scale Penn Foster's healthcare B2B sales portfolio, focused exclusively on healthcare employers and healthcare workforce-development partners.

This is a true builder role—not an optimization role. You will architect and lead the healthcare sales engine from the ground up, establishing the strategy, structure, relationships, and operating rigor required to scale healthcare B2B revenue and learner completions over the next five years.

The ideal candidate will have 7+ years of consultative enterprise sales, strategic partnerships, business development, or healthcare workforce-development experience and will report directly to the Vice President of Sales.

Essential Job Functions

Own the Full Healthcare Sales Cycle

• Identify, prospect, and engage new healthcare enterprise accounts.

• Develop and execute outbound strategies across priority healthcare segments.

• Lead complex, multi-stakeholder healthcare sales cycles from first touch through close and expansion.

• Build and manage a high-quality healthcare enterprise pipeline.

• Develop strategic account plans for health systems and other priority healthcare organizations.

Sell Consultatively to Healthcare Employers

• Lead with “Why Change, Why Now”—helping healthcare organizations understand their workforce challenges before positioning solutions.

• Diagnose customer needs across talent acquisition, workforce shortages, internal mobility, upskilling, retention, and career advancement.

• Understand the operational and financial realities of healthcare employers and connect workforce challenges to measurable business outcomes.

• Partner with the Director of Strategy and Solutions to create tailored workforce-development solutions aligned to healthcare employer outcomes.

• Navigate and influence multiple stakeholders, including executives and leaders across HR, Talent Acquisition, Learning & Development, Workforce Development, Operations, Clinical Operations, Pharmacy, Nursing, and Community/Partnership functions.

Build the Healthcare GTM Engine

• Help define Penn Foster's healthcare ideal customer profile, priority segments, target accounts, and buying personas.

• Develop market intelligence on healthcare workforce trends, talent shortages, training capacity, and employer priorities.

• Test and iterate on healthcare messaging, value propositions, sales plays, and partnership models.

• Identify emerging healthcare workforce needs that can inform Penn Foster's solutions and go-to-market strategy.

Drive Results With Discipline

• Maintain accurate pipeline, forecasting, account plans, and opportunity management.

• Operate within defined sales stages and methodology (CVI).

• Consistently meet or exceed healthcare revenue targets.

• Build repeatable sales processes that can scale across healthcare segments.

• Develop land-and-expand strategies within strategic healthcare accounts.

Priority Healthcare Workforce Challenges

The Director will develop partnerships around high-priority workforce challenges, including:

• Shortages of allied-health professionals.

• Difficulty recruiting qualified candidates into high-demand healthcare roles.

• Limited capacity in traditional healthcare education and training programs.

• Long time-to-fill for critical frontline positions.

• Employee turnover and retention challenges.

• Barriers to internal mobility and career advancement.

• Need for flexible education that employees can complete while working.

• Geographic gaps in access to healthcare training.

• Demand for apprenticeship, pre-apprenticeship, work-based learning, and earn-while-you-learn models.

• Pressure to improve workforce productivity while maintaining quality patient care.

Knowledge, Skills & Abilities

Healthcare Mission Alignment

• Passionate about expanding access to high-quality, flexible, career-aligned healthcare education.

• Excited to work at the intersection of healthcare workforce development, patient care, and economic mobility.

Builder Mentality

• Experience operating in early, evolving, or entrepreneurial healthcare GTM environments.

• Comfortable with ambiguity and creating structure where it does not yet exist.

Consultative Enterprise Sales Experience

• Proven track record of success in enterprise, consultative sales.

• Experience selling complex workforce, education, technology, services, or partnership solutions to healthcare organizations.

• Strong ability to lead with the customer's workforce problem rather than a product pitch.

• Experience with sales process frameworks such as CVI, MEDDPICC or similar consultative/value-based sales methodologies.

Healthcare Business Acumen

• Strong understanding of healthcare employer economics, workforce challenges, and organizational structures.

• Familiarity with health systems, hospitals, ambulatory care, pharmacy, post-acute care, or other healthcare environments.

• Ability to connect workforce-development initiatives to measurable outcomes such as hiring, retention, internal mobility, productivity, time-to-fill, and cost avoidance.

Strategic Thinking

• Strong business acumen and problem-solving skills.

• Ability to define target healthcare customers, market segments, buying personas, sales plays, and messaging as the business evolves.

• Ability to identify patterns across healthcare customer conversations and turn market feedback into strategic recommendations.

Clear & Compelling Communicator

• Excellent verbal and written communication skills.

• Ability to communicate credibly with healthcare professionals and leaders at every level—from frontline leaders and individual contributors to C-suite executives and board-level stakeholders.

• Strong executive presentation, discovery, negotiation, and storytelling skills.

Requirements

• Minimum 7 years of experience in consultative enterprise sales, strategic partnerships, business development, fundraising, healthcare workforce development, or a closely related field.

• Demonstrated success selling to or partnering with healthcare organizations.

• Healthcare industry experience strongly preferred; direct experience with health systems, hospitals, or healthcare employers is highly desirable.

• Proven ability to build and manage a complex enterprise pipeline.

• Demonstrated success working across multiple healthcare stakeholders and organizational functions.

• Experience working in an evolving or high-growth environment.

Working Conditions & Hiring Process
• 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, and similar activities. 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 bringing together 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 learners to achieve long-term success in the workplaces of the future.  Our history dates 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 diverse teams – 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, and free access to our online programs.