Compensation: 65.000 - 80.000
Executive Director
Position Type: Full-Time Location: Remote/Hybrid, with periodic travel to West Point, alumni events, board meetings, and partner convenings Reports To: Board of Directors Compensation: $65-80K; commensurate with experience
About The Strong Gray Line
The Strong Gray Line strengthens the West Point community by equipping graduates and their families with tools for resilience, fostering connection through care and camaraderie, and honoring the legacy of those who served and sacrificed.
Founded by members of the West Point Class of 2004, The Strong Gray Line is expanding its work to serve graduates and families across the Long Gray Line. Through peer connection, mental health readiness, care coordination, remembrance, and alumni engagement, The Strong Gray Line exists to ensure that no graduate or family member walks alone.
Our work is organized around three core pillars:
Stand To – Ready: Equipping graduates and families with practical tools for mental and emotional readiness.
Grip Hands – Connected: Strengthening connection and coordinating care when classmates, graduates, or families are in need.
Honor: Preserving the legacy of service and sacrifice through remembrance, storytelling, and tribute initiatives.
Position Summary
The Strong Gray Line seeks a mission-driven, entrepreneurial Executive Director to lead the organization through its next stage of growth. The Executive Director will serve as the organization’s primary strategic and operational leader, responsible for advancing the mission, building sustainable systems, growing partnerships, supporting the Board of Directors, and expanding the organization’s reach across the West Point alumni community.
This is a unique opportunity for a leader who understands the culture of service, the importance of trusted peer networks, and the need for confidential, practical support for graduates and their families. The ideal candidate will be equally comfortable casting vision, building infrastructure, cultivating donors, managing programs, and representing the organization with credibility and care.
The Executive Director will also help strengthen The Strong Gray Line’s public presence, ensuring the organization is visible, credible, and mission-aligned online so that graduates, families, donors, partners, and supporters can more easily understand, engage with, and advance its work.
Key Responsibilities
Strategic Leadership
The Executive Director will work closely with the Board to refine and execute The Strong Gray Line’s strategic plan, ensuring that the organization grows with clarity, focus, and sustainability. This includes translating the mission and pillars into measurable goals, annual priorities, program plans, and organizational rhythms.
The Executive Director will help define what success looks like for the organization, including how The Strong Gray Line measures connection, readiness, care coordination, alumni engagement, remembrance, and community impact.
Fundraising and Donor Development
The Executive Director will lead the organization’s fundraising strategy and help build a sustainable revenue base. This includes cultivating individual donors, major gifts, class-based giving, foundation support, sponsorships, and other philanthropic partnerships.
Responsibilities include developing donor materials, supporting board members in fundraising, managing donor relationships, identifying new funding opportunities, and communicating the impact of The Strong Gray Line’s work in a compelling and credible way.
Program Oversight and Growth
The Executive Director will oversee the development, coordination, and evaluation of The Strong Gray Line’s core programs, including Mental Health First Aid training, peer readiness tools, alumni connection efforts, care coordination, Grip Hands events, and remembrance initiatives.
The Executive Director will ensure programs are mission-aligned, well-executed, confidential where appropriate, and responsive to the real needs of graduates and families.
Care Coordination and Partnership Development
A central part of The Strong Gray Line’s work is helping graduates and families access support through trusted relationships and coordinated referrals. The Executive Director will help strengthen the organization’s care coordination model, including partnerships with platforms, veteran-serving organizations, alumni networks, mental health resources, and community providers.
The Executive Director will ensure the organization has appropriate processes, boundaries, confidentiality practices, and referral pathways in place to support graduates and families responsibly.
Board Engagement and Governance
The Executive Director will partner closely with the Board of Directors to support effective governance, decision-making, fundraising, and strategic oversight. This includes preparing board materials, reporting on organizational progress, helping manage committees or working groups, and ensuring the Board has the information and tools needed to govern well.
The Executive Director will also help strengthen board engagement and support future board development as the organization grows.
Communications and Alumni Engagement
The Executive Director will serve as a key ambassador for The Strong Gray Line, communicating the mission clearly and consistently to graduates, families, donors, partners, West Point stakeholders, and the broader alumni community.
This includes supporting newsletters, donor communications, event messaging, storytelling, impact reports, alumni outreach campaigns, and other communications that build trust, awareness, and engagement. The Executive Director should be able to communicate with warmth, discretion, professionalism, and authenticity.
Online Visibility and Mission Advancement
The Executive Director will help expand The Strong Gray Line’s visibility across appropriate online platforms in a way that advances the organization’s mission, causes, programs, and community reach. This includes ensuring that the organization’s digital presence clearly communicates its purpose, pillars, impact, events, stories, and opportunities for involvement.
Responsibilities may include supporting website content, social media presence, digital storytelling, online campaigns, thought leadership, partner amplification, event promotion, donor engagement, and mission-centered communications that increase awareness across the West Point alumni community and beyond.
The Executive Director should be comfortable representing The Strong Gray Line online with professionalism, discretion, warmth, and credibility, while maintaining appropriate boundaries around sensitive personal, family, mental health, or care coordination matters.
Operations and Organizational Management
As the organization grows, the Executive Director will be responsible for building strong internal systems. This may include budgeting, financial oversight, compliance, data tracking, volunteer management, technology platforms, program calendars, contractor management, and administrative processes.
The Executive Director will help move The Strong Gray Line from a founder- and volunteer-driven initiative toward a durable, professionally managed nonprofit organization.
Ideal Candidate Profile
The ideal candidate is a trusted, mission-centered leader who understands the West Point community and can build bridges across generations, classes, families, and partner organizations. This person is both strategic and practical, able to inspire others while also creating the systems needed to execute.
Strong candidates will bring many of the following qualities:
- Deep commitment to the mission of The Strong Gray Line and the West Point community
- Understanding of military, veteran, or military family culture
- Experience leading a nonprofit, program, initiative, campaign, or growing organization
- Demonstrated ability to fundraise, cultivate donors, or build philanthropic partnerships
- Strong relationship‑building skills and high emotional intelligence
- Excellent written and verbal communication skills
- Comfort building an organization’s online visibility through mission‑driven storytelling, digital engagement, social media, website content, newsletters, or public‑facing communications
- Ability to work with discretion, especially around sensitive personal or family needs
- Experience working with a board, advisory group, or senior volunteer leadership team
- Comfort operating in a startup or growth‑stage environment
- Ability to manage both strategy and execution
- Strong organizational skills and follow‑through
- Commitment to honoring service, sacrifice, connection, and care
Preferred Qualifications
- Prior nonprofit leadership or executive‑level management experience
- Fundraising, donor development, or major gifts experience
- Familiarity with West Point, the Long Gray Line, or service academy communities
- Experience with veteran support, mental health readiness, care coordination, peer support, or family support programs
- Experience building systems, partnerships, programs, or volunteer networks
- Experience growing awareness, engagement, or support for a mission‑driven organization through online platforms, digital campaigns, social media, thought leadership, or community storytelling
- Comfort representing an organization publicly and with senior stakeholders
Personal Attributes
- Mission‑first
- Trustworthy and discreet
- Relational and collaborative
- Entrepreneurial and resourceful
- Clear and compelling in communication
- Comfortable being a visible, credible representative of the organization online and in person
- Comfortable with ambiguity and growth
- Respectful of tradition while able to build for the future
- Deeply committed to the belief that no graduate or family member should walk alone
Success in the First Year
In the first year, the Executive Director will be expected to:
- Build strong working relationships with the Board and key volunteers
- Refine organizational priorities and create an actionable annual plan
- Strengthen fundraising strategy and donor communications
- Support growth of core programs under the Stand To, Grip Hands, and Honor pillars
- Improve operational systems, reporting, and program tracking
- Expand awareness and engagement across the West Point alumni community
- Strengthen The Strong Gray Line’s online visibility and digital engagement in support of its mission, programs, donor development, alumni outreach, and broader causes
- Help position The Strong Gray Line for long‑term sustainability and impact
To Apply
Interested candidates should submit a resume and cover letter describing their interest in The Strong Gray Line, relevant leadership experience, and connection to the mission.
The Strong Gray Line is an equal opportunity organization. We welcome candidates who bring diverse experiences, backgrounds, and perspectives and who share our commitment to strengthening the Long Gray Line.
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