Operating Executive Jobs in Connecticut (NOW HIRING)

The salary range for this role is between $215,000-$220,000 annually.

Founded in 1988 by Paul Newman, The Hole in the Wall Gang Camp provides "a different kind of healing" to thousands of children with serious illnesses and their families annually - all completely free of charge. For many of these children and families, Hole in the Wall provides multiple Camp experiences throughout the year at the facility in Ashford, Conn, in dozens of hospitals and clinics, directly in camper homes and communities and through other outreach activities across the Northeast and Mid-Atlantic.

The Chief Operating Officer (COO) serves as the senior operational and financial leader of The Hole in the Wall Gang Fund, Inc. This position is responsible for the integrated management of the organization’s operational infrastructure including finance, human resources, information technology, and capital projects. The COO is responsible for optimizing day-to-day internal operations and translating strategic plans into actionable priorities ensuring that the organization remains financially sound and resources are managed effectively for program and staff excellence and long term sustainability. As a key member of the executive leadership team, the COO will collaborate closely with the Chief Executive Officer.

• Partner with the Director of Finance to develop and present the annual operating and capital budgets, multi-year financial forecasts, and endowment projections.
• Monitor budget performance throughout the year, ensuring that program and operational expenditures align with approved plans and that variances are identified and addressed promptly.
• Provide strategic oversight of organizational financial planning, budgeting, forecasting, reporting, and expense control to ensure mission scaling and fiscal sustainability.
• Identify and mitigate operational, legal, and regulatory risks, ensuring compliance with all nonprofit governance standards.
• Oversee the annual audit process, enforce internal financial controls, and ensure compliance with GAAP.
• Present financial data and operational metrics at regular meetings of the Finance and Investment Committees as well as at Board of Directors meetings.
• Partner with the CHRO on talent strategy including recruitment, performance management, compensation and benefits, and professional development.
• Ensure that human resource initiatives, policies, and practices support organizational growth, workforce stability, missional alignment, and positive employee experience.
• Partner with the CHRO and executive leadership team to strengthen workforce planning, succession planning, leadership development, and staff engagement initiatives.
• Oversee the organization’s information technology function including managed service provider relationships.
• Ensure that staff have the tools and resources they need and that the infrastructure support efficient and secure program and administrative operations and aligns with organizational growth.
• Partner with organizational leaders to evaluate and implement technology solutions that advance mission delivery and operational efficiency.
• Serve as organizational point of accountability for active capital construction and facility projects, including the Maryland expansion and any future facility investments.
• Ensure project milestones, budgets, and risks are monitored regularly, with change orders managed within contingency parameters.
• Coordinate with external contractors, architects, and county agencies as needed to advance project goals.
• Serve as a senior member of the CEO’s executive leadership team, contributing to organizational strategy, cross-functional planning, and senior team cohesion.
• Represent the organization in external relationships with vendors, government agencies, accrediting bodies, and peer organizations.
• Support the CEO in board engagement, including preparation of reports, presentations, and materials for Board meetings and relevant committees.
• Perform other duties as assigned.

• Minimum ten years of progressively responsible leadership experience in nonprofit management, operations, or closely related field, with at least 7 in a senior leadership role.
• Demonstrated financial management expertise, including budget oversight, audit coordination, and board-level reporting.
• Proven success in multi-site or multi-program environments.
• Experience in indirect service organizations, preferably those serving children, families, or individuals with serious health conditions.
• A master’s degree in business administration, nonprofit management, or a certified public accountant license or a related discipline preferred.
• Strong financial acumen and deep competency in budget development, financial modeling, and risk management with extensive knowledge of nonprofit accounting standards, grant compliance, and restricted fund management.
• Superior analytical, problem-solving, decision-making, and project management skills.
• Proven ability to lead complex, multi-functional teams across geographically distributed operations.
• Exceptional interpersonal and communication skills, with the ability to build trust across diverse internal and external stakeholders.
• Knowledge of IT/business infrastructure.
• Familiarity with accreditation standards relevant to residential camp, healthcare, and youth service programs.
• Proficiency in Microsoft Office Suite; familiarity with Blackbaud Financial Edge, Salesforce, or comparable systems preferred.
• Deep commitment to the mission of The Hole in the Wall Gang Camp and to serving children and families with serious illnesses with excellence and dignity.
• Excellent judgment in navigating risk, safety, and compliance in a regulated, high-stakes service environment.
• The ability to establish positive relationships with a variety of people in multicultural environments.
• Base office in New Haven, CT with a hybrid work model.
• A valid driver’s license and driving record which meets HITWG insurance carrier requirements.
• The ability to operate a computer for extended periods of time with appropriate breaks.

The Hole in the Wall Gang Camp is a very competitive salary, a generous benefits package, and growth opportunities for high contributors.

The Hole in the Wall Gang Camp is an Equal Opportunity Employer, does not discriminate on the basis of age, creed, color, national origin, ancestry, marital status, sexual orientation, gender identity or expression, disability, nationality or sex, and is committed to a diverse workforce.