Chief Financial Officer

Jacob's Pillow (Diane Carlyle Executive Search)

Job Description


THE OPPORTUNITY

Over the last decade, Jacob’s Pillow has grown in every dimension. Year-round staff has increased from 36 to 53, and the organization’s reach now extends well beyond the Berkshires through online programming, international partnerships, and a significant investment in its digital platform through the Bloomberg Digital Accelerator. The completion of the $30-million Doris Duke Theatre in 2025 – one of three performance stages on the 220-acre campus – reflects both the ambition of the institution and the deep commitment of the community that has made the Pillow what it is. As the organization approaches its 100th anniversary in 2032, it has never been better positioned — or more ready — to grow.

That growth demands financial leadership, systems, and infrastructure commensurate with what Jacob's Pillow has become and what it intends to be, and the organization is seeking an inaugural Chief Financial Officer to lead this work. By assuming primary operational and financial leadership for finance, IT, and facilities, the CFO will enable the Artistic and Executive Director to have more time to focus on artistic vision, partnership development, external fundraising and strategic planning. Reporting directly to Artistic and Executive Director Pamela Tatge, the CFO will be a key member of the senior leadership team and a trusted partner to her and the Board in shaping the financial and operational foundation from which Jacob’s Pillow will continue to build. Currently, Jacob's Pillow has an operating budget of $14.7 million, an endowment of $24.9 million, and a year-round staff of 53. During the 10-week summer Festival, the staff grows to 140.

Given the nature of the role and the rhythms of a residential performing arts campus, the CFO must be based within one hour of Jacob’s Pillow in Becket, Massachusetts, and spend the majority of their time on-site throughout the year.

CORE RESPONSIBILITIES

  • Serve as a credible, trusted, and strategic thought partner to the CEO, Board, and the executive team — shaping financial and organizational strategy through forward-looking insight and scenario planning and bringing the independent judgment and candor that sound financial leadership requires.
  • Act as the primary financial liaison to the Board of Trustees and the Finance Committee, including providing executive oversight of the annual audit process and investment portfolio management.
  • Working with the Director of Finance, ensure the full range of financial operations — including cash management, payroll, grants compliance, and vendor and contract management — are well-run, well-controlled, and aligned with organizational priorities.
  • Oversee the IT function with a strategic lens — treating technology as an enabler of programming, audience experience, and organizational effectiveness, not merely a cost center; partner with the Director of IT to address both immediate infrastructure needs and longer-term priorities.
  • Oversee facilities planning and capital budgeting in close partnership with the Director of Facilities, supporting the development of short- and long-term maintenance and capital investment plans across Jacob’s Pillow’s 200-acre campus; partner with the Director of Facilities as staff liaison to the Board of Trustees Facilities Committee, ensuring the Board has the information and analysis needed to support sound decision-making.
  • Lead the continued evolution of the finance function, building systems, structures, and capabilities that enable long-term sustainability and organizational effectiveness.
  • Drive the development of meaningful business intelligence, including multi-year financial models, scenario analyses, and other actionable insights.
  • Partner with the incoming Chief People Officer to clarify shared accountabilities — including payroll authority and HRIS integration — and to co-lead an enterprise systems review in the CFO’s first year.
  • Identify and implement opportunities to leverage technology, including AI and automation, to improve efficiency, reduce manual work, and enhance decision-making.
  • Oversee all organizational insurance programs — including general liability, property, event, and workers’ compensation — managing carrier relationships, annual renewals, and claims in coordination with legal counsel and relevant department heads.
  • Lead and develop a high-performing team, strengthening team structure, clarity, and accountability.
  • Partner with the Chief Philanthropy Officer to align financial and philanthropic reporting, support endowment stewardship and growth in advance of the organization’s centennial in 2032 and serve as a financial resource in donor relationships when appropriate.
  • Model and reinforce Jacob’s Pillow’s adaptive, transparent, and mission-centered culture.

CANDIDATE PROFILE

Jacob’s Pillow’s Chief Financial Officer will be a seasoned executive and organizational leader who brings the expertise to strengthen its financial infrastructure as well as the curiosity, flexibility, and interpersonal skills to thrive in a nonprofit performing arts organization with a complex operating model. A strategic partner to the Artistic and Executive Director, the Board, and every member of the senior leadership team, the ideal candidate will possess an affinity for Jacob’s Pillow’s mission and be energized by the opportunity to have a meaningful impact in advancing one of the world’s leading performing arts organizations.

EXPERIENCE

  • 10+ years of progressive senior finance leadership experience
  • BA/BS required; CPA, MBA, or equivalent credential preferred
  • Knowledge of nonprofit finance, including multi-fund and restricted fund accounting, grants management, GAAP, and federal and state compliance
  • Demonstrated success leading budgeting, forecasting, and long-term financial planning in a complex organization with multiple revenue streams
  • Demonstrated experience building or rebuilding financial infrastructure, such as strengthening a monthly close process, implementing budget modeling tools, and integrating disparate financial systems
  • Experience overseeing audit and financial reporting, including 990 preparations
  • Fluency with CRM-integrated financial environments; familiarity with Tessitura preferred

CAPABILITIES

Strategic Leadership: Jacob’s Pillow has grown rapidly and has much to build, both to support its current scale as well as its aspirations for the future. At the same time, in any mission-driven organization, the successful candidate must be able to balance the dynamic tension that inevitably exists between available resources and ambitious vision. Serving as a trusted thought partner to the CEO, Board, and senior leadership team, the CFO:

  • Establishes priorities in a target-rich environment, distinguishing between what must be done now, what can be sequenced, and what can be delegated — and communicates that framework clearly to the CEO and the Board
  • Invests in the systems that allow management and staff to operate at a genuinely strategic level
  • Centers the mission without sacrificing financial discipline by demonstrating a willingness to come up with workable solutions 
  • Grounds problem-solving in clear thinking: defines the real issue, names the risks of action and inaction, quantifies impact, and presents options with full costs including opportunity costs
  • Anticipates the questions the CEO and Board will ask before they ask them; brings issues forward with context, options, and a recommendation rather than waiting to be asked

Collaboration: Jacob’s Pillow is a complex year-round organization that also operates a 10-week festival every summer. Supporting the work of every department, the CFO must be a leader who puts the institution first and:

  • Approaches each department as a genuine collaborator, conveying curiosity about their work and investment in their success
  • Acts as a forward-looking strategic partner, seeking ways to add value and support the work
  • Builds trust through consistent follow-through — communicates clearly about timelines, delivers on commitments, and proactively flags when circumstances change
  • Translates complex financial information into accessible, actionable language for non-finance colleagues
  • Provides the tools, information, and support to empower department leaders to understand their budgets and take genuine ownership of them

Leading Change and Building Shared Ownership: The CFO will inherit a function and position that will need to grow to keep pace with Jacob’s Pillow. Building the infrastructure and culture of shared financial accountability that the organization needs, now and in the future, will require a CFO who:

  • Leads with patience and intentionality, investing the time to understand the organization and its culture
  • Engages stakeholders early and often in the development of new processes, systems, and policies to build alignment
  • Fosters transparency by helping teams understand the “why” behind new systems and controls while staying connected to the mission as the organizing principle
  • Implements stronger systems and financial discipline in service of — not at the expense of — the distinctive culture and artistic mission of a performing arts organization
  • Models and reinforces a culture of transparency, flexibility, and integrity

COMPENSATION

The salary range for this position is $160,000 to $200,000, commensurate with experience. Jacob’s Pillow offers a generous benefits package including medical, dental, and vision insurance through Blue Cross Blue Shield of MA, Delta Dental, and VSP, with coverage beginning day one of employment, plus an employer-funded Health Reimbursement Arrangement (HRA) that covers the majority of the medical deductible. Employees can also enroll in pre-tax Flexible Spending Accounts for medical and dependent care. Life insurance and AD&D (up to 3x salary), short- and long-term disability, the Employee Assistance Program, and travel assistance are all 100% employer-paid. Time off includes paid vacation, holidays, and sick leave, alongside Massachusetts Paid Family & Medical Leave through a private plan with Unum. For retirement, we offer a 403(b) plan with a 2% employer contribution toward annual salary. On campus during the Summer Festival season, employees enjoy three free meals a day, complimentary tickets to performances, and access to Pillow programs and archives.

CONTACT AND PROCESS

Jacob’s Pillow has retained Diane Carlyle Executive Search (www.dcxsearch.com) to support the search for the Chief Financial Officer. We welcome comments, nominations, or expressions of interest. All applicants are asked to include a letter of interest with their resume. Please send an email with supporting materials to: JPCFO@dcxsearch.com

Not sure you meet 100% of the qualifications? Research shows that some candidates apply for jobs when they fulfill an average of 60% of the criteria, while others tend to apply only if they meet every requirement. If you believe that you could excel in this role, we encourage you to apply. We are dedicated to considering a broad array of candidates, including those with diverse workplace experiences and backgrounds.

Jacob’s Pillow is a registered 501(c)(3) not-for-profit organization that provides equal opportunity for all employees and applicants for employment without regard to race, color, creed, religion, gender, sexual orientation, national origin, age, marital status, mental or physical disability, pregnancy, military or veteran status, or any other basis prohibited by state or federal law.