CEO - On the Road Collaborative

Organizational Description:

On the Road Collaborative (On the Road) is a non-profityouth empowerment organization headquartered in Harrisonburg, (VA) with program services throughout the Shenandoah Valley.

Our mission is to empower middle and high school youth by providing equal access to educational opportunities and hands-on career experiences. Through our unique after-school and summer learning programs, we connect our youth to trusting adult relationships and equitable opportunities, enrich their lives with additional learning opportunities that inspire growth, and empower our youth to realize and fulfill their promise.

We currently have a $1.2 million annual operating budget with 8 full-time and 40 part-time employees, operating 5 program sites across three cities (Harrisonburg, Staunton & Waynesboro), serving 400 youth on average annually.

Position Overview:

The Chief Executive Officer (CEO) is the chief leader, ambassador and strategist of the organization. The CEO is a people-centered leader who has an unyielding commitment to educational equity and empowering youth, a passion for fostering community connections and change, and thrives in a dynamic and growth-oriented environment.

Reporting to the Board of Directors and working in close partnership with the Staff Leadership Team, the CEO is primarly responsible for advancing the mission, developing and executing strategy, enhancing culture and policies, strengthening program impact, ensuring financial health and positioning the organization for long-term growth and sustainability.

Key responsibilities by function include:

• Organizational Leadership (40%)
• Program Impact & Operations (30%)
• External Relations & Fundraising (20%)
• Financial Management & Business Administration (10%)

ESSENTIAL Roles and Responsibilities:

Organizational Leadership (40%):

• Mission and Vision : Collaborate with the Board of Directors and the Staff Leadership Team in setting and living into the organizational mission and vision
• Strategy : Ensure that the organization has a long-range strategyand a clear plan to implement that leads to consistent and timely progress
• Ambassador: Continuously cultivate and steward a broad range of relationships with community leaders, donors, funders and civic & government partners on a local/state/national level that leads to increased resources, reputation and visibility
• Board: Provide timely, accurate and actionable information to the Board, support board recruitment and engagement efforts, and collaborate with the Chair and the Board as a whole to ensure effective governance and strategic decision making
• Staff Leadership Team: Foster an effective “leadership team” that works together towards the achievement of the organizational mission and goals
• Organizational Culture: Establish a dynamic, inclusive culture that embodies our core values of equity, relationships, growth, and empowerment, and is supported by effective human resource structures and organizational policies
• School Partners: Sustain transformational partnerships with existing school division leadership, and when necessary, cultivate new relationships with future school partners

Program Impact & Operations (30%):

• Program Director Supervisor: Supervise and provide strategic direction and support for the two Regional Program Directors, ensuring ongoing programmatic excellence and achievement of goals
• Evaluation and Impact: Oversee the development and implementation of the program evaluation plan that drives continuous improvement and impact, regularly sharing results with key stakeholders
• Safety and Compliance: Champion a culture of youth safety, ensuring the highest standards of child protection, staff training, and compliance with mandated reporting laws
• Professional Development Plan: Work with the Program Directors to establish the annual training plan for Youth Leaders and other personnel that is aligned with program goals; Encourage and seek out opportunities for on-going staff education
• Data Systems: Ensure effective, secure data systems are in place and that staff are trained and accountable for their use
• Grant Management: Understand relevant On the Road grant awards and work with Program Directors to ensure timely completion of reports and compliance

External Relations & Fundraising (20%):

• Branding and Communication: Oversee the organization’s branding guide and external communication strategy, and ensure effective implementation
• Fundraise: Collaborate with the Director of Development and Finance in raising funds for the organization; Serve as primary relationship manager for major donors and institutional funders
• Career Enrichment: Support efforts to recruit Community Teachers for all program sites
• Media: Serve as the primary media contact for the organization

Financial Management & Business Administration (10%):

• Stewardship: Oversee budgeting, financial reporting, and risk management in partnership with the Director of Development & Finance and the Board
• Signatory: The CEO shall have authority to sign checks, drafts, notes, and all other orders for the payment of money and to sign the corporate name to all deeds, contracts, leases, and other documents of every nature and description
• Systems: Oversee the various organizational operational systems, including but not limited to: Google Suite and Zoom
• Other: Support Human Resource functions and other administrative duties as required

Characteristics and Qualifications:

While there are many paths to success, the following characteristics and qualifications will most likely set you up to excel in this role:

• Unwavering commitment to On the Road Collaborative’s mission and Diversity, Equity and Inclusion (DEI)
• Passion, idealism, integrity, positive attitude and self-directed
• Excellence in organizational management with the ability to coach staff, manage and develop high-performance teams, and set and achieve strategic goals
• Proven leader with a track record of running high-quality youth programs and/or teaching that deliver positive outcomes
• Exceptional written and verbal communication skills; a persuasive and passionate communicator with excellent interpersonal skills
• Strong attention to detail with a love for data and using information to celebrate successes and drive continuous improvement
• Action-oriented, entrepreneurial, adaptable, problem solver
• Tenacious and humble with a deep sense of personal accountability
• Bachelor’s degree; or equivalent work experience

Position Details:

• Reports to: Board Chair
• Position Type: Full Time, Exempt
• Location: On the Road’s headquarters is located in Harrisonburg (VA) in The Harrisonburg Innovation Hub, with programs currently operating in Harrisonburg, Staunton, and Waynesboro cities. This position would currently involve sharing time between the Harrisonburg (60%) and Staunton/Waynesboro/Augusta County areas (40%)
• Compensation Benefits

- Flexible Work Policy: Full-time employees are able to work on a mobile basis for an average of two or three days per week, whenever reasonable and feasible.
- Starting salary range is $85,000 - $95,000 with opportunities for annual increases.
- Competitive Benefits Package, including access to medical and vision insurance and group disability and life insurance
- Generous paid-time off policy: 40 paid days off per year between holidays, breaks and PTO
- Professional Development: Opportunities throughout the year to participate in trainings and conferences
- Gas Stipend paid monthly in a pre-paid gas card
- Computer: Laptop provided to conduct all On the Road work

Job Requirements:

• Must have a valid driver’s license and access to a vehicle
• Ability to work some evenings and weekends as needed to deliver programming and fulfill organizational commitments

How to Apply:

• Email cover letter and resume to: work@ontheroadcollaborative.com by

Monday, February 16, 2026.

• The anticipated start date is May-June 2026.
• For confidential inquiries or assistance with the application process, please contact Jen Yoo Gulliver via email (jen@ontheroadcollaborative.com) or phone (540-360-1123).
• For more information regarding this position, please visit our website at https://www.ontheroadcollaborative.com/work-with-us/

Pay: $85,000.00 - $95,000.00 per year

Benefits:

• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Work Location: In person

Salary : $85,000 - $95,000