Director, Sales

• 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.

• 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.

• 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.

• 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.

• 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.

• Passionate about expanding access to high-quality, flexible, career-aligned education.
• Excited to work at the intersection of workforce development and economic mobility.

• Experience operating in early, evolving, or entrepreneurial GTM environments.
• Comfortable with ambiguity and creating structure where it does not yet exist.

• 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.

• 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.

• 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.

• 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.

• 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.