President & CEO

Maryland Nonprofits; Annapolis (MD); On-site; USD 150,000 - 210,000; Full time

Benefits offered by this job

Health insurance

Retirement contributions

Job summary

Chesapeake Region Accessible Boating (CRAB) seeks a President & CEO to lead the organization from its Annapolis Adaptive Boating Center, engaging guests, staff, volunteers, and partners on-site and in the community.

The incoming leader will bring 10+ years of nonprofit leadership, a strong fundraising record, governance expertise, and a passion for inclusion and mission impact across the Chesapeake Bay region.

Qualifications

• At least 10 years of leadership experience in a nonprofit or mission-driven entity.
• Proven fundraising success including donations, grants, sponsorships, and government support.
• Strong governance experience and collaboration with boards and committees.
• Strategic thinker capable of translating vision into plans, systems, and actions.

Responsibilities

• Partner with the Board to advance CRAB’s mission and strategic direction.
• Ensure excellent delivery of mission-aligned programs and establish systems to evaluate impact and feedback.
• Cultivate partnerships and explore opportunities to extend CRAB’s reach; national profile.

Skills

Nonprofit leadership

Fundraising

Board governance

Strategic planning

Public speaking

Relationship building

Financial acumen

Staff development

Volunteer engagement

Community partnerships

Emotional intelligence

Annapolis area connections

Job description

President & Chief Executive Officer

Chesapeake Region Accessible Boating (CRAB)

Chesapeake Region Accessible Boating (CRAB) provides the therapeutic benefits of sailing to people with disabilities, recovering warriors, and youth from underserved communities. CRAB was founded in 1991 by Annapolis resident Don Backe with the principle that people with disabilities can and should be able to live fulfilling and joyful lives and have equitable access to meaningful outdoor therapeutic recreation on the Chesapeake Bay. After several decades operating from Sandy Point State Park, CRAB opened a state-of-the-art Adaptive Boating Center (ABC), a multi-year public‑private effort to create a permanent waterfront facility designed for accessibility and sustainability.

Today, the ABC is recognized as the premier facility in the world for people with disabilities to learn to sail or go boating and reaches more than 1,500 guests annually through family and group sailing, sailing clinics and camps, adaptive fishing and powerboating, regattas, radio‑controlled sailing, and year‑round wellness and educational activities. Its no‑cost programming is delivered by a trained corps of volunteer skippers, crew, and other professionals who work together to ensure participants have a safe and fulfilling experience on the Chesapeake Bay. Learn more at crabsailing.org.

After more than a decade of transformative leadership, CRAB’s President & CEO, Paul “Bo” Bollinger, will retire at the end of 2026. The incoming President & CEO will inherit an organization with a strong reputation, deeply committed staff and volunteers, an equally active and committed Board, and an extraordinary purpose‑built waterfront campus with the capacity to expand CRAB’s impact for years to come.

The President & CEO oversees an operating budget of approximately $1 million and reports to a Board of Directors of 13 business and civic leaders from Annapolis and the greater Washington region. The President & CEO supervises a team of five and a corps of seven Fleet Directors. CRAB seeks a deeply relational and hands‑on executive who will be equally comfortable engaging guests and volunteers on the waterfront, cultivating donors and community partners, and collaborating with the Board and staff on organizational strategy.

Key Responsibilities include:

Strategy, Programs, and Impact

• Partner with the Board to advance CRAB’s mission and strategic direction.
• Ensure excellent delivery of mission‑aligned programs and establish systems to evaluate impact, outcomes, and feedback.
• Cultivate partnerships and explore opportunities to extend CRAB’s reach; national profile.

Fundraising, Visibility, and External Relations

• Serve as CRAB’s chief ambassador and spokesperson and strengthen its visibility.
• Partner with the Development Director and Board to strengthen giving.
• Personally cultivate major donors and other key stakeholders while maintaining productive relationships with government partners and exploring mission‑aligned strategic partnerships and earned‑revenue opportunities.

Organizational Leadership and Volunteer Engagement

• Lead, develop, and retain a talented professional team and establish effective systems, policies, procedures, accountability, and opportunities for professional growth.
• Foster an inclusive, collaborative, mission‑centered culture characterized by respect, transparency, teamwork, high standards, and care.
• Sustain and strengthen CRAB’s volunteer community.

Financial, Facility, and Governance Stewardship

• Ensure sound financial management and organizational sustainability, including budgeting, financial reporting, cash‑flow monitoring, internal controls, and compliance.
• Steward CRAB’s significant physical assets, including the Adaptive Boating Center, marina, fleet, and equipment, with appropriate maintenance, safety, capital planning, and long‑term asset‑replacement strategies.
• Serve as principal staff liaison to the Board and partner with Board leadership on governance, recruitment, onboarding, engagement, succession, and development.

Experience, Skills and Qualities

• Passion for CRAB’s mission and commitment to expanding opportunities, independence, inclusion, and quality of life for people with disabilities, recovering warriors, and youth from underserved communities.
• At least 10 years of leadership experience, preferably in a nonprofit or mission‑driven entity.
• Strategic and creative thinker who can translate vision into plans, systems, and action.
• Engaging and persuasive communicator with strong public speaking, writing, storytelling, and relationship‑building skills.
• Significant fundraising experience, including a record securing donations, grants, sponsorships, and government support.
• Strong business and financial acumen, including budgeting, forecasting, financial reporting, risk management, and organizational sustainability.
• Accomplished people leader with experience coaching staff and fostering a positive, accountable, and collaborative culture.
• High emotional intelligence, sound judgment, integrity, and ability to build trust with diverse stakeholders.
• Experience partnering effectively with a nonprofit Board and committees, with a strong understanding of governance.
• Knowledge of and connections to Annapolis, Maryland and/or the Chesapeake Bay is considered a plus.
• Meaningful recreational boating and/or sailing experience, including knowledge of waterfront operations, safety, weather, and fleet management, is considered a plus.
• Personal or professional ties to disability‑serving organizations and organizations serving recovering warriors and youth from underserved communities are considered a plus.

Compensation & Benefits

The Board has set a salary range of $TBD, commensurate with experience. CRAB offers a generous benefits package including health insurance and retirement contributions.

Working Location

The President & CEO works primarily from CRAB’s Adaptive Boating Center in Annapolis, Maryland and will be highly engaged on‑site with CRAB’s guests, staff, volunteers, and partners.

The nature of CRAB’s work requires flexibility and on‑site availability, including programs, community meetings, donor engagements, regattas, fundraising events, and other activities that may occur during evenings and weekends. The role also includes local and regional travel, with occasional travel beyond the region as appropriate.

Equal Opportunity Employer

CRAB is an Equal Opportunity Employer.