President & Chief Executive Officer

Chesapeake Region Accessible Boating (CRAB)

Status: Full-time, exempt employee

Salary: $140,000 - $150,000

Location: Annapolis, Maryland

Reports to: Board of Directors 

Deadline: Early November for best consideration.

About Chesapeake Region Accessible Boating

Chesapeake Region Accessible Boating (CRAB) provides the therapeutic benefits of sailing to people with disabilities, recovering warriors, and youth from underserved communities. CRAB 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.

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. A serious car accident left Don paralyzed in his mid-50s, and his friends got him back on a sailboat to bring joy back to his life. From that moment on, Don’s personal mission was to bring the thrill and freedom of sailing to people with disabilities. 

After several decades operating from Sandy Point State Park, CRAB opened the Adaptive Boating Center (ABC), a state-of-the-art waterfront facility designed for accessibility and sustainability. The ABC was a public-private effort with support from the State of Maryland, Anne Arundel County, and the City of Annapolis, complemented by millions of dollars in private philanthropy. Today, the ABC is recognized as a premier facility in the world for people with disabilities to learn to sail or go boating. Learn more at crabsailing.org. 

Leadership Opportunity

After more than a decade of transformative leadership, including envisioning and implementing the ABC project, CRAB’s President & CEO, Paul “Bo” Bollinger, will retire at the end of 2026. The incoming President & CEO (President) will inherit an organization with a strong reputation, mission-driven staff and volunteers, an active Board, and an extraordinary purpose-built waterfront campus with the capacity to expand CRAB’s impact for years to come. 

Working in partnership with the Board, staff, volunteers, donors, and community partners, the President will guide CRAB into a chapter of growth and opportunity. With the ABC fully operational, the President will lead stakeholders through a process of envisioning the future: strengthening programs, expanding partnerships, increasing visibility, and ensuring CRAB has the people, systems, and resources to support sustainable growth. The incoming leader will preserve the qualities central to CRAB’s success—including an unwavering commitment to its guests, an exceptional culture of volunteerism, and rigorous attention to safety—while bringing fresh perspective to how CRAB can extend its reach and leadership in adaptive recreation. 

Financial sustainability will continue to be a central priority. The President will partner closely with the Development Committee, staff, and the full Board to deepen individual philanthropy, expand corporate and foundation support, strengthen planned and endowment giving, and sustain productive relationships with government partners. They will also steward CRAB’s significant physical assets and consider how its expanded capacity can support new opportunities, with ideas ranging from year-round programming and events to initiatives that further establish CRAB as a national thought leader in adaptive sailing and boating.

The President 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 supervises a team of five (Development Director, Finance and Administration Manager, Marketing and Events Manager, Program Manager, and Deputy Program Manager), and oversees a corps of seven Fleet Directors who ensure CRAB guests have a safe and memorable experience at the ABC. 

CRAB seeks a deeply relational and hands-on executive to provide visionary leadership and day-to-day management that steers CRAB toward the effective execution of its mission. The President will be equally comfortable engaging guests and volunteers on the waterfront, cultivating donors and community partners, stewarding government partners, and collaborating with the Board and staff on organizational strategy. An appreciation of sailing and/or recreational boating—and the safety, operational, and stewardship responsibilities of a waterfront organization—will be additive to the leader’s effectiveness. They will bring emotional intelligence, sound judgment, and an inclusive leadership style to guide CRAB in the next chapter of its ambitious and successful trajectory. 

Key Responsibilities

Strategy, Programs, and Impact

• Partner with the Board to advance CRAB's mission and strategic direction; translate long-term priorities into annual plans, goals, budgets, and measurable outcomes.
• Ensure excellent delivery of mission-aligned programs that provide meaningful and fulfilling experiences for guests; establish systems to evaluate impact, outcomes, and feedback. 
• Cultivate partnerships with disability-serving organizations, other nonprofits, boating organizations, government agencies, and other institutions to extend reach and impact.
• Explore opportunities to advance CRAB's national profile in adaptive boating, including competitive sailing, training, and certification initiatives.
• Ensure safety remains central to CRAB's programs and operations, with appropriate risk management, procedures, training, oversight, and continuous improvement.

Fundraising, Visibility, and External Relations

• Serve as CRAB's chief ambassador and spokesperson, communicating the organization's mission and impact to guests, donors, partners, media, and the broader community.
• In partnership with the Development Director and the Board's Development Committee, implement a comprehensive fundraising strategy that strengthens annual campaigns, major gifts, planned giving, endowment support, sponsorships, grants, and government funding.
• Personally cultivate and steward relationships with major donors, corporate partners, foundations, government leaders, and other key stakeholders.
• Establish a culture of philanthropy that engages and equips Board members to participate meaningfully in fundraising, relationship development, and donor recognition.
• Strengthen CRAB's visibility and brand among disability communities, the broader boating community, veterans organizations, philanthropy, and prospective guests and volunteers.
• Maintain productive relationships with the City of Annapolis, Anne Arundel County, the State of Maryland, and other government partners; represent CRAB effectively in regulatory, permitting, funding, and public-policy matters relevant to its mission.
• Over time, identify strategic partnerships and earned-revenue opportunities that strengthen CRAB's financial sustainability while remaining aligned with its mission.

Organizational Leadership and Volunteer Engagement

• Lead, develop, and retain a talented professional team, establishing clear goals and responsibilities, accountability, communication, and opportunities for professional growth.
• Establish effective internal systems, policies, and procedures that support a growing and increasingly sophisticated organization.
• Assess CRAB's organizational structure as the ABC and programs evolve, ensuring staffing and responsibilities align with organizational priorities, resources, and seasonal needs.
• Foster an inclusive, collaborative, mission-centered culture characterized by respect, transparency, teamwork, high standards, and care for CRAB's guests and one another.
• Sustain and strengthen CRAB's volunteer community, including directing recruitment, training, development, engagement, and recognition programs.
• Ensure volunteer and staff training protocols reflect current safety practices, accessibility standards, and CRAB's expectations for the guest experience.

Financial, Facility, and Governance Stewardship

• Ensure sound financial management and organizational sustainability; partner with the Treasurer and Finance Committee to develop realistic annual budgets, monitor financial performance and cash flow, and provide timely, accurate reporting.
• Oversee accounting, payroll, audits, insurance, contracts, legal and regulatory compliance, and other administrative functions.
• Maintain appropriate policies, internal controls, financial procedures, and organizational documentation consistent with GAAP and applicable laws and regulations.
• Steward CRAB's significant physical assets, including the ABC, marina, fleet, and equipment, ensuring appropriate maintenance, safety, capital planning, and long-term asset-replacement strategies.
• Oversee the boat donation program, including inspection, valuation, and disposition.
• Serve as the principal staff liaison to the Board of Directors, maintaining transparent communication and providing the information and support necessary for effective governance and policymaking.
• Partner with the Board Chair and Governance Committee on Board recruitment, onboarding, engagement, succession, and development.
• Support Board committees and ensure coordination among members, staff, and volunteers.

Experience, Skills and Qualities 

While we understand that no single candidate can possess every qualification listed below, the following are priority areas.

• 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 of 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. Experience leading small teams is considered a plus.
• Emotional intelligence, sound judgment, integrity, and ability to build trust with diverse stakeholders.
• A strong understanding of governance and experience partnering effectively with a nonprofit Board and committees.

Considered a major plus:

• Knowledge of and connections to Annapolis, Maryland, and/or the Chesapeake Bay.
• Meaningful recreational boating and/or sailing experience, with knowledge of waterfront operations, safety, weather, and fleet management. 
• Personal or professional ties to nonprofits serving people with disabilities, veterans, and youth from underserved communities.

Compensation

The Board has set a salary range of $140,000-$150,000, commensurate with experience, with a generous benefits package that includes health insurance and retirement contributions.

Working Location

The President & CEO works primarily from CRAB's Adaptive Boating Center and will be highly engaged on-site with CRAB's guests, staff, volunteers, and partners.

CRAB's work requires flexibility, and the President will participate in programs, community meetings, donor engagements, regattas, fundraising events, and other activities that may occur during evenings and weekends. The role will include local and regional travel for meetings with partners, donors, and government leaders, with occasional travel beyond the region.

Application Process

CRAB has retained the services of Good Insight, a Washington, DC-based executive search firm exclusively focused on the nonprofit sector. Interested applicants should submit a PDF resume and a cover letter that describes their interest in and qualifications for this role. Upload application materials at good-insight.org/careers.

For best consideration, apply by early November. Qualified applicants will be contacted on a rolling basis. Early applications are encouraged due to the pace of the search. Direct confidential inquiries to search leads Carlyn Madden and Tej Pikle at CRAB@good-insight.org.

Equal Opportunity Employer

CRAB is an Equal Opportunity Employer.