Chief Executive Officer

Overview

On the Road Collaborative (On the Road) is a non-profit youth 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 after-school and summer learning programs, we connect youth to trusting adult relationships and equitable opportunities that inspire growth and empower youth to realize their potential.

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.

For more information about On the Road, visit our website.

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 primarily 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.

• Organizational Leadership (40%)
  • MISSION and VISION:
    Collaborate with the Board of Directors and the Staff Leadership Team in setting and living the organizational mission and vision
  • STRATEGY:
    Ensure that the organization has a long-range strategy and a clear plan to implement that leads to consistent and timely progress
  • AMBASSADOR:
    Cultivate and steward relationships with community leaders, donors, funders and civic & government partners at local/state/national levels to increase resources, reputation and visibility
  • BOARD:
    Provide timely, accurate, and actionable information to the Board; support board recruitment and engagement; collaborate with the Chair and Board for governance and strategic decision making
  • STAFF LEADERSHIP TEAM:
    Foster an effective leadership team working toward the organizational mission and goals
  • ORGANIZATIONAL CULTURE:
    Establish an inclusive culture that embodies core values of equity, relationships, growth, and empowerment, supported by HR structures and policies
  • SCHOOL PARTNERS:
    Sustain transformational partnerships with existing school division leadership and cultivate new relationships with future school partners
• Program Impact & Operations (30%)
  • PROGRAM DIRECTOR SUPERVISION:
    Supervise and provide strategic direction for the two Regional Program Directors to ensure programmatic excellence
  • EVALUATION & IMPACT:
    Oversee development and implementation of the program evaluation plan; share results with key stakeholders
  • SAFETY & COMPLIANCE:
    Champion youth safety, ensure high standards of child protection, staff training, and mandated reporting compliance
  • PROFESSIONAL DEVELOPMENT PLAN:
    Work with Program Directors to establish annual training for Youth Leaders and personnel; encourage ongoing staff education
  • DATA SYSTEMS:
    Ensure effective, secure data systems and staff accountability for their use
  • GRANT MANAGEMENT:
    Understand relevant grants and ensure timely reporting and compliance
• External Relations & Fundraising (20%)
  • BRANDING & COMMUNICATIONS:
    Oversee branding guide and external communication strategy, ensuring effective implementation
  • FUNDRAISE:
    Collaborate with the Director of Development and Finance in raising funds; serve as primary relationship manager for major donors and institutional funders
  • CAREER ENRICHMENT COURSES:
    Support efforts to recruit Community Teachers for all program sites
  • MEDIA:
    Serve as the primary media contact for the organization
• Financial Management & Administration (10%)
  • STEWARDSHIP:
    Oversee budgeting, financial reporting, and risk management in partnership with the Director of Development & Finance and the Board
  • SIGNATORY: CEO authority to sign checks,…