Chief Executive Officer

The Hole in the Wall Gang Fund, Inc.

Location: Connecticut

Reports To: Board of Directors

Status: Full-Time, Exempt

Compensation: Competitive and commensurate with experience; salary range compliant with local transparency laws

Organizational Overview

Founded by Paul Newman in 1988, The Hole in the Wall Gang Fund, Inc. (the “Organization”) provides a different kind of healing to thousands of children with serious illnesses and their families—always free of charge. Through two residential camps in the Northeast and Mid-Atlantic, extensive year-round programs in hospitals, and family-based support services, the Organization delivers hope, fun, and community to children navigating some of life’s toughest challenges. With a current annual operating budget of $25 million and a dedicated staff across multiple sites, the Organization is entering a pivotal period of growth. A $150 million comprehensive campaign is underway to support the development, launch, and long-term sustainability of a second Hole in the Wall campus in Maryland, significantly expanding its reach throughout the Mid-Atlantic region and beyond.

Position Summary

The Chief Executive Officer (CEO) is the chief strategist, enterprise leader, and mission steward of The Hole in the Wall Gang Fund, Inc. Reporting to the Board of Directors, the CEO provides vision, oversight, and operational excellence across all facets of the Organization, ensuring that programs, people, culture, strategy, and resources are aligned to deliver exceptional impact and long-term sustainability. The CEO partners closely with the Board, senior leadership team, and community of supporters to advance the Organization’s mission. As a highly visible ambassador, the CEO strengthens national awareness, expands philanthropic partnerships, and guides the successful execution of the comprehensive campaign—while ensuring operational excellence, financial strength, program quality, risk management, and a vibrant, inclusive culture across all sites.

Key Responsibilities

Strategic Leadership & Governance

• Lead the creation, execution, and evaluation of a multi-year strategic plan that advances mission, ensures program excellence, and supports sustainable growth.
• Partner with the Board of Directors to implement best-practice governance, foster strong communication, and support effective board engagement in strategy, fundraising, and oversight.
• Serve as a unifying and inclusive leader who inspires staff, volunteers, donors, families, and partners around a shared vision.

Fundraising & Campaign Leadership

• Serve as a primary strategic partner in the $150 million comprehensive campaign—engaging major donors, institutional partners, and new supporters across the Northeast and Mid-Atlantic.
• Work closely with the Chief Development Officer, Board, and Campaign Steering Committee to develop cultivation strategies and open new philanthropic markets.
• Champion a strong fundraising culture throughout the organization, ensuring alignment of philanthropic goals with strategic priorities, program needs, and organizational capacity.

Organizational & Operational Leadership

• Provide enterprise-level oversight across programs, operations, finance, DEI, risk management, marketing, and development.
• Partner with the COO and senior leadership team to ensure operational excellence, staff development, regulatory compliance, safety, and effective multi-site coordination.
• Maintain fiscal strength by guiding annual and long-term budgeting, financial planning, investment decisions, and resource allocation in partnership with the CFO/COO and Finance Committee.

External Relations & Mission Advocacy

• Serve as the Organization’s leading spokesperson—representing the mission with authenticity, empathy, and clarity.
• Build collaborative relationships with hospitals, community partners, policymakers, peer organizations, and media to elevate visibility and expand the Organization’s reach.
• Strengthen the Organization’s reputation as a national leader in camp-based programs, pediatric illness support, and year-round family services.

Culture, People, and Leadership Development

• Foster an inclusive, values-driven culture rooted in compassion, excellence,safety, and joy—reflective of the Organization’s origins and the communities it serves.
• Lead, mentor, and support a high-performing senior team, ensuring clarity ofroles, accountability, professional growth, and cross-functional collaboration.
• Champion diversity, equity, and inclusion across all programs, staff practices, volunteer engagement, and community partnerships.

Ideal Candidate Profile

The next CEO is an inspiring and authentic leader who brings a combination of strategic vision, operational excellence, fundraising acumen, and deep commitment to children and families. While no single candidate will have every qualification, strong candidates will demonstrate:

• Successful executive leadership experience within a complex, mission-drivennonprofit, healthcare, or child/family services organization.
• Experience leading or partnering on significant fundraising efforts, campaigns, orphilanthropic initiatives.
• Ability to build meaningful relationships with donors, partners, families, staff, andcommunity leaders across diverse geographies.
• Demonstrated skill in leading multi-site operations and teams during periods ofgrowth or transformation.
• Strong communication skills, including public speaking, mission storytelling, andmedia representation.
• High emotional intelligence, cultural competence, and a leadership stylegrounded in empathy and integrity.
• Passion for the Organization’s mission and for delivering joy, healing, andcommunity to children with serious illnesses.

Qualifications

• 10+ years of progressively responsible leadership experience; CEO or seniorexecutive experience strongly preferred.
• Experience managing senior teams and complex operations, ideally acrossmultiple sites or program lines.
• Proven ability to cultivate major philanthropic relationships and contribute to significant fundraising initiatives.
• Bachelor’s degree required; advanced degree in business, nonprofit management, healthcare administration, or a related field preferred.

Compensation and Benefits

The Hole in the Wall Gang Fund, Inc. offers a competitive salary range and comprehensive benefits package, including health insurance, retirement contributions, generous PTO, and professional development support. Compensation is commensurate with experience and compliant with applicable transparency laws.

Equal Opportunity Employer

The Hole in the Wall Gang Fund, Inc. is committed to building a diverse, inclusive, and equitable community. We welcome candidates from all backgrounds and experiences and are proud to be an Equal Opportunity Employer.

• 10 Paid Holidays
• 27 Days Paid Time Off
• Paid Parental Leave (both parents)
• Paid Bereavement Leave
• Paid Jury Duty
• Telework Opportunities for Select Positions
• Tuition Reimbursement
• Healthcare Plan (Medical, Dental, Vision, Prescription)
• Medical Co-Pay and Insurance Deductible Reimbursement
• Life Insurance
• Long-Term Disability Insurance
• Wellness Reimbursement
• 403(b) and Roth 403(b) Retirement Plans