Senior Director, Sales

Title: Director, Sales

Location: United States

Director, Sales

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 to build and scale Penn Foster's B2B sales portfolio, focused exclusively on employers, social purpose organizations and workforce-development partners.

This is a true builder role—not an optimization role. You will architect and lead the sales engine from the ground up, establishing the strategy, structure, relationships, and operating rigor required to scale 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 workforce-development experience and will report directly to the Vice President of Sales.

Essential Job Functions

Own the Full Sales Cycle

Identify, prospect, and engage new enterprise accounts and social purpose orgs.

Develop and execute outbound strategies across priority segments.

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

Build and manage a high-quality enterprise pipeline.

Develop strategic account plans for employers and other priority organizations.

Sell Consultatively to Employers & Social Purpose Organizations

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

Diagnose needs across talent acquisition, workforce shortages, internal mobility, upskilling, retention, mission-based purpose and career advancement.

Understand the operational and financial realities of employers and social purpose organizations, connecting workforce challenges to measurable outcomes.

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

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

Build the GTM Engine

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

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

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

Identify emerging 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, for example).

Consistently meet or exceed revenue targets.

Build repeatable sales processes that can scale across segments.

Develop land-and-expand strategies within strategic accounts.

Priority Workforce Challenges

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

Shortages of skilled professionals.

Difficulty recruiting qualified candidates into high-demand roles.

Limited capacity in traditional 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 training.

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

Knowledge, Skills & Abilities

Mission Alignment

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

Excited to work at the intersection of workforce development and economic mobility.

Builder Mentality

Experience operating in early, evolving, or entrepreneurial 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 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.

Business Acumen

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

Familiarity with the operational elements of social purpose organizations, including mission, funding and audiences served.

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 customers, market segments, buying personas, sales plays, and messaging as the business evolves.

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

Clear & Compelling Communicator

Excellent verbal and written communication skills.

Ability to communicate credibly with 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, workforce development, or a closely related field.

Demonstrated success selling to or partnering with organizations.

Social purpose industry experience strongly preferred; direct experience with employers is highly desirable.

Proven ability to build and manage a complex enterprise pipeline.

Demonstrated success working across multiple 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.