Jacob’s Pillow seeks a Deputy Director of Philanthropy to sustain, deepen, and expand a variety of fundraising avenues for the Pillow, including highest level Membership, Major Gifts programs, planned giving, and program underwriting by high net worth individuals and other donors who have the potential of increasing their Pillow giving.

The Deputy Director of Philanthropy reports to the Director of Philanthropy and is responsible for managing a portfolio of approximately 200 donors and prospects. The Deputy Director of Philanthropy will directly supervise the Manager of Membership & Individual Support, helping guide all Pillow fundraising strategies and tactics for increasing contributed income from individuals.

This position may be based either at Jacob’s Pillow’s home in the Berkshires in Becket, Massachusetts, or in New York City, and can include working remotely during a great deal of the year. During the summer Festival (mid-June through late August) the position will be based on-site in the Berkshires.

The Deputy Director of Philanthropy is responsible for cultivating and stewarding prospects, conducting prospect research and wealth tracking, managing reporting on donor gifts, and closing a significant number of major gifts each year, working closely with senior staff at the Pillow and the Board of Directors.

COVID vaccination is required as a condition of employment. Reasonable accommodations will be considered. A person is fully vaccinated for COVID-19 more than 2 weeks after having received the second dose in a 2-dose series (Pfizer-BioNTech or Moderna), or more than 2 weeks after having received a single-dose vaccine (Johnson and Johnson [J&J]/Janssen).

Duties & Responsibilities

  • Manage a portfolio of prospects and current donors, maintaining frequent personalized contact.
  • Qualify, cultivate, and solicit donors for funding to meet the Pillow’s individual support priorities and fundraising goals.
  • Design and implement effective strategies and tactics to actively engage donors and lead to solicitations and closed pledges and gifts.
  • Lead the School Sponsorship program, growing this important resource and using it as a stepping stone for increased engagement.
  • Spearhead creative thinking for innovative gift proposals that inspire donors to make major gifts, and handle all steps of the gift, pledge, and fulfillment processes.
  • Expand the Individual Giving area of Pillow fundraising at all levels by supervising the Manager of Membership and Individual Support to cultivate these relationships to more actively result in additional and increased gifts.
  • Work closely with the Director of Philanthropy to develop methods that increase individual fundraising while supporting the Pillow’s clear and stated goals in inclusion, diversity, equity, and access.
  • As needed, provide support to involve the Director of Jacob’s Pillow, Director of Philanthropy, other key staff members, and volunteer leadership in developing prospect relationships.
  • Produce briefing materials and post-visit follow-up communications.
  • Meet budgetary and planning goals for visits, solicitations, and gift closing.
  • Promptly record meetings and essential information in the database and manage prospects and gifts at the highest level.
  • Analyze activities to measure progress.
  • Effectively utilize administrative support and delegate tasks as appropriate.

Required Qualifications

  • Experience working in non-profit organizations (preferably arts and/or dance-focused).
  • Bachelor’s degree or equivalent academic experience.
  • Minimum seven years of fundraising experience and a track record of success in initiating and closing major gift solicitations, and in managing staff.
  • Excellent verbal and written communication skills.
  • Superior interpersonal skills; genuine interest in people.


  • Must be self-motivated with a passion for meeting and exceeding goals.
  • Strong strategic and tactical thinker and planner.
  • Demonstrated ability to engage in collaborative problem-solving with prospects and colleagues; highly organized in portfolio and time management.
  • Must be able to establish and maintain excellent rapport with donor constituents and colleagues.
  • Able to operate both independently and as an active participant in team-based strategies.
  • Ability to exercise sound judgment, diplomacy, confidentiality, and to exhibit a mature, professional, and positive approach at all times.
  • Versatile in standard office computer skills and online database systems.

To Apply: Please email cover letter, resume, and three references to [email protected] with “Deputy Director of Philanthropy” in the subject line.

All inquiries and materials will be confidential. Please do not mail hard copies.