Come work with us

Executive Director

Are you an entrepreneurial individual who has a sixth sense for the people, work, technologies, and trends that are driving the future of arts, culture, and media? Were you telling your friends about Sally Rooney and Sheck Wes in 2016? Virgil Abloh and Greta Gerwig in 2009? If you were or wish you had been, we invite you to apply for the executive director opening at Twenty Summers.

Twenty Summers is seeking an executive director to oversee its operations and programs, while developing its strategy and guiding its growth. The executive director will be responsible for all aspects of the organization, including fundraising, programming, grant- and copywriting, marketing, and operations.

The successful candidate will be passionate about arts and culture, highly versatile, creative, and entrepreneurial—someone who is eager to solve open problems, whether conceiving a new series of programs, sourcing and negotiating a new partnership, or building a fundraising and marketing strategy. And you will be comfortable interacting with a range of stakeholders from local sponsors to institutional donors and from emerging artists to top talent. You can do much of the work remotely, but the position will require you to be in Provincetown during May and June and on other occasions, in addition to making trips to Boston and New York City.

To apply, please email a resume and cover letter to


  • Work with board to develop strategic direction and programmatic initiatives.

  • Develop, optimize, and oversee organizational budget.                   

  • Meet quarterly and annual fundraising goals. Successfully grow and retain donor base of local businesses, individuals, foundations, and corporate sponsors.

  • Work with directors and partners to develop programming.                    

  • Develop and maintain relationships with talent representatives including publicists, managers, agents, and gallerists to book events.

  • Serve as the organization’s public face and cultivate relationships between Twenty Summers, potential guests, and the press.

  • Negotiate contracts and manage relationships with vendors.

  • Write grant applications and copy for collateral.

  • Grow the audiences for Twenty Summers’ programs, both online and in-person.

  • Maintain Twenty Summers' social media, website, email marketing, and blog presences.

  • Develop and track success metrics for programs and events to assess financial health, audience demographics and growth, and cultural impact.

  • Provide regular reporting to board and drive agendas for monthly board calls. 

  • Form co-marketing and sponsorship agreements with local and national organizations.

  • Oversee and direct the production, post-production, distribution and marketing of audio/video content.

  • Perform regular competitive analysis and make recommendations based on results.

  • Work with designers and strategists to create and implement local and national marketing campaigns.

  • Maintain and optimize Twenty Summers' online advertising accounts.

  • Recruit and manage advisory board, volunteers, seasonal workers, and interns.

  • Manage, maintain, and negotiate Twenty Summers’ facilities.


  • Demonstrated passion for the arts of all types. You take an interest in what’s happening at the cutting edge of the arts and in pop culture.

  • Entrepreneurial drive to develop and execute new initiatives with little guidance or oversight. Problems and challenges motivate you to find solutions.

  • Ability to scale teams and organizations.

  • Ability to fundraise from both large and small donors, including institutions and corporations.

  • Strong writing skills.

  • Proven ability to attract top talent.        

  • College graduate. Study in relevant field (business, art or art history, communications, nonprofit or museum administration) a plus.

  • Experience producing cultural content for a general audience with a demonstrated ability to anticipate, understand, and exploit opportunities in the landscape of cultural programming and media.

  • Successful history of growing audiences for cultural content.

  • Leadership experience managing several concurrent projects.                  

  • Experience soliciting bids, negotiating contracts, and managing relationships with outside service providers.                    

  • Adept with social media, Squarespace, HTML, Adobe Creative Suite, Microsoft Office, Eventbrite, Square, Salesforce, YouTube, Vimeo, MailChimp, G Suite, Google AdWords, and Facebook ads. Understanding of how to use negotiation and technology to streamline budgets and workflow.

  • Familiarity with 501(c)(3) compliance.                         

  • Experience managing volunteer teams.

  • Knowledge of arts, cultural, and philanthropic communities. Having local networks in Boston and Cape Cod is a plus.  

Volunteer with Twenty Summers

We are always seeking multiple volunteers to help us out during and leading up to our spring season. We will be hosting concerts and conversations open to the public in the beautiful Barn over the course of five weekends, as well as an artist residency program during the weekdays. In exchange for your volunteer work, you get free tickets to the show you work for, and have a great opportunity being involved in an exciting non-profit arts center on Cape Cod!

Tasks may include:
· Checking tickets at the door
· Ushering
· Parking Attendant
· Assisting with artists and backstage
· Helping out with deliveries/pick ups
· Putting up posters and dropping off flyers
· Social media
· Anything that comes up!

We are looking for friendly, flexible people who will be available for two or more events. If you can do them all, then even better! Please note the Hawthorne Barn is located up a long dirt path and steep staircase. Email if you’d like to join our team!


Twenty Summers is seeking a Marketing & Development (Fundraising) Intern to support the organization in discovering and contacting new potential donors and sponsors, developing existing relationships, grant-writing, marketing outreach, social media, and assisting in coordinating fundraising events. 

This is a remote, unpaid position, requiring 10 hours per week, working closely with the executive director, and will provide the intern with a valuable experience working with a nonprofit arts organization on development, outreach, marketing, donor management, and events. Ideal candidate is a self-motivated, organized student or recent graduate who can commit to at least 3 months, and be available for weekly or bi-weekly check-ins with the director. Course-credit is available for current students.

· Identify, research, and develop new relationships for sponsorships/donations
· Assist Executive Director with grant-writing and funding applications
· Help create and implement fundraising marketing campaign
· Manage online database of donors/sponsors and potential donors/sponsors
· Assist with social media and marketing efforts

· Must have own computer
· Current college student or recent graduate preferred
· Interest or major/minor in Nonprofits, Fundraising, Arts Administration, Art History, Business Development, or Marketing
· Excellent communication and writing skills
· Strong organizational skills and self-structured
· Experience with Excel and/or Google Docs
· Familiarity with Salesforce a bonus but happy to teach
· Experience with fundraising or grant-writing a bonus but not required

· Interns receive 4 tickets to events of their choice during our 2019 spring festival of concerts and conversations May and June, 2019 in Provincetown, Mass. 
· This internship will provide the intern with a valuable experience working with a nonprofit arts organization on development, outreach, fundraising marketing, donor management, and events.
· Credit available for current students.
· Training provided as needed

Note on Location: While our organization is based in Provincetown, all staff and board members work remotely from New York, Maine, and Massachusetts. Applicants are welcome to apply from any location.

To apply, please send a resume and cover letter to