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Director of Development

On the Road Collaborative
Harrisonburg, VA Full Time
POSTED ON 7/16/2026
AVAILABLE BEFORE 11/13/2026

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. Our programs are offered for youth in Harrisonburg City (Skyline Middle School, Thomas Harrison Middle School and Harrisonburg High School) and Waynesboro City (Kate Collins Middle School and Waynesboro High School). We serve 300 youth on average each year.

How to Apply:

  • Please email work@ontheroadcollaborative.com with your resumé and cover letter

Position Overview:

The Director of Development is a newly created, full-time role that is central to the financial sustainability and growth of On the Road Collaborative. Reporting to the CEO, this individual will lead all fundraising efforts, cultivate and steward a diverse donor base, and manage grant-seeking and reporting activities. This is an exciting opportunity for a mission-driven development professional to build and grow a fundraising program at a high-impact, community-rooted organization.

Key responsibilities by function include:

  • Direct Fundraising and Donor Stewardship (50%)
  • Grant Writing and Reporting (40%)
  • Administration and Data (20%)

ESSENTIAL Roles and Responsibilities:

Direct Fundraising and Donor Stewardship (50%):

Serve as the chief fundraiser, responsible for creating and executing a comprehensive strategy that includes building a sustainable private revenue portfolio reaching toward or surpassing $250,000 annually and securing significant on-going investments from the localities we serve. Fosters a spirit of philanthropy throughout the organization, ensuring that organizational culture and systems support fundraising efforts.

  • STRATEGY: Develop a strategy to maintain a healthy, diversified, and growing revenue mix from private and public sources
  • PHILANTHROPIC SUPPORT: Lead efforts in securing philanthropic support from individuals, corporations and foundations to fund the operational budget and plan for future sustainability
  • EVENTS: Provide vision and leadership for fundraising events that leads to increased revenues and community support
  • STRATEGIC PARTNERSHIPS: Maintain and deepen strategic community partnerships with organizations like local governments, United Way, Community Foundation, and Virginia’s Department of Education
  • DONOR DATABASE: Manage the Bloomerang donor database system
  • REPORTS: Prepare quarterly and annual reports and financial analyses for the Board of Directors on progress toward financial goals and provide guidance to achieve objectives

Grant Writing and Reporting (40%):

Serve as the chief financial officer and supervise the Coordinator of HR, Finance & Admin to manage a range of business administration functions:

  • MAINTAIN AND GROW: a portfolio of foundation and government grants, including the Virginia 21st Century Community Learning Centers (21CCLC) program and Community Foundation of Central Blue Ridge
  • RESEARCH: and qualify new grant opportunities aligned with On the Road Collaborative’s programs and strategic direction
  • WRITE: clear, compelling, and accurate grant proposals and letters of inquiry
  • TRACK: all grant deadlines, requirements, and reporting obligations; ensure timely submission of all interim and final reports
  • COLLABORATE: with program staff to gather outcome data, stories, and documentation needed for grant proposals and reports
  • MAINTAIN: strong, communicative relationships with foundation program officers and institutional funders

Administration and Data Management (20%):

  • MANAGE: the organization’s donor database/CRM, ensuring accurate and up-to-date records for all gifts, contacts, and correspondence
  • PROCESS: gifts promptly and ensure accurate, timely acknowledgment of all donations
  • REPORT: On the results of for the Executive Director and Board of Directors, including progress toward revenue goals

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
  • Outstanding written and verbal communication skills; a persuasive and passionate communicator with excellent interpersonal skills
  • Track record in fundraising and knowledge of effective practices for shepherding prospects and stewarding donors to support On the Road’s mission with sustained investments
  • Excellence in organizational management with the ability to set and achieve strategic goals, supervise and coach staff, and manage budgets and other administrative tasks
  • Detail-oriented with a love for numbers
  • Tenacious and humble with a deep sense of personal accountability
  • Action-oriented, entrepreneurial, adaptable, problem-solver
  • Content knowledge of youth development and public education is a plus
  • Bachelor’s degree; or equivalent work experience

Preferred Qualifications:

  • 3 years of experience in nonprofit fundraising, development, or a closely related field

Position Details:

  • Reports to: CEO
  • Location: On the Road’s headquarters is located in Harrisonburg (VA) in The Harrisonburg Innovation Hub
  • Salary: $60,000-70,000 depending on experience
  • 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.
  • Position Type: Full Time, Exempt

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:

  • Please email work@ontheroadcollaborative.com with your resumé and cover letter

Pay: $60,000.00 - $70,000.00 per year

Benefits:

  • Flexible schedule
  • Health insurance
  • Paid time off

Work Location: In person

Salary : $60,000 - $70,000

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