Regional Director - Hampton Roads

Location: Norfolk, VA

Compensation: $70,000–$95,000 incentive pay stipend for benefits and work-related expenses

About Opportunity Scholars

Opportunity Scholars (OS) is a nonprofit organization dedicated to helping high school seniors and young adults pursue career and technical education. We guide, connect, and finance young adults to achieve career success through low-cost pathways to high-paying jobs.

By building these pathways, we create a pipeline of capable, dependable technical workers to strengthen local businesses and regional economies.

The Role

Opportunity Scholars is seeking a Regional Director to lead the launch and operations of our programs in the Hampton Roads region. This is a ground-up leadership role, ideal for a strategic, relationship-oriented professional ready to build systems, grow a team, and make a measurable impact.

The Regional Director will establish OS’s presence, cultivate community and employer partnerships, supervise a local team, and drive the implementation of career pathway programs that support young adults across the region.

Why Join Us

• Lead a new regional office with the opportunity to shape the organization’s local impact.

• Build partnerships and programs that directly support young adults and local employers.

• Competitive salary and incentive structure, with a stipend to offset work-related expenses.

• Opportunity to work in a mission-driven, collaborative, and high-impact environment.

Key Responsibilities

• Regional Leadership & Strategy: Serve as the lead representative of OS in Hampton Roads. Shape regional rollout strategy, build awareness, and establish trust with local stakeholders. Identify key geographic areas, community partners, and employer sectors to focus initial program efforts.

• Employer Engagement: Proactively identify and develop partnerships with employers in high-demand industries. Secure work-based learning opportunities for scholars, including internships, apprenticeships, and “earn and learn” pathways. Maintain ongoing communication with employers, resolve challenges, and advocate for investment in workforce development.

• Team Leadership: Grow the regional team over time to meet student and program needs. Foster a scholar-centered culture focused on outcomes, retention, and career success.

• Operations & Coordination: Coordinate with OS headquarters to ensure consistent program delivery, branding, and communication. Manage regional operations, including event planning, student onboarding, scheduling, and local marketing.

• Community & Workforce Collaboration: Partner with local economic development agencies, schools, and workforce stakeholders to align OS programs with regional employer needs. Identify high-priority technical career tracks and develop strategies for engagement with Career and Technical Education teachers and work-based learning coordinators.

• Representation & Advocacy: Represent OS at local and regional workforce development groups, promoting opportunities for young adults and employer collaboration.

• Performance Tracking & Reporting: Track and report key performance indicators (KPIs) including student enrollment, employment placement, partner engagement, and program outcomes. Collect data to inform continuous improvement and impact storytelling. Collaborate with leadership to evaluate regional success and guide expansion strategy.

• Other Duties: Perform additional responsibilities as assigned.

Qualifications

• 5 years of experience in workforce development, education, business development, or a related field.

• Proven record of building relationships across industries, schools, and community groups.

• Supervisory experience preferred.

• Bachelor’s degree or equivalent experience required.

• Knowledge of CTE programs, trades professions, or workforce training programs is a plus.

• Strong communication, public speaking, and strategic planning skills.

• Comfortable traveling throughout the Hampton Roads region as needed.

Personal Attributes

• Passion for helping young adults access education and achieve career success.

• Self-starter with strong ownership and accountability.

• Highly relational with the ability to build trust across diverse stakeholders.

• Strategic thinker who can execute operational plans effectively.

How to Apply

Please submit your resume to kari@OpportunityScholars.org with the subject line: Regional Director – Hampton Roads – [Your Name].

Applications will be reviewed by our hiring team on a rolling basis until the position is filled.