Current Job Opportunities

Chester Theatre Company is seeking a Managing Director for our summer theatre located in Chester, Massachusetts. Now in it’s 37^th season, Chester Theatre Company produces contemporary professional Equity theatre in an intimate setting, creating community and offering audiences fresh perspectives on vital issues. We present exceptional performances, tell diverse stories, hold important conversations, lead theatre trips, educate across generations, and develop and support new work. We are committed to theatre as a means to explore and celebrate our shared humanity.

Our rural location, about 30 minutes from Northampton, MA and 30 minutes in the other direction from Pittsfield, MA, and close to the many cultural destinations of the Berkshires, provides a unique opportunity to bring together local residents from throughout Western Massachusetts and summer residents to enjoy plays that speak to the issues we are confronting every day in our lives. We hold talk backs after almost every performance and our audiences enthusiastically take part in discussions of our work.

Chester is a small town of about 1200 people. The town is supportive of the theatre and performances take place in a transformed town hall with 120 seats.

The annual budget is about $500,000.

Michelle Ong-Hendrick and Christopher Baker took over the artistic leadership of the theatre in January of 2025 and produced a season of work that was very well received by audiences and critics alike. The theatre is on an upward trajectory with ticket sales in the 2025 season up by 20%. The theatre has a group of dedicated board members and donors who consistently make annual gifts.

Since January of 2025, the administrative duties have been handled by Deb Clapp, interim managing director. Deb will stay on until a new managing director is appointed.

The managing director will be expected to run the day to day operation of the theatre including overseeing marketing, box office, front of house, bookkeeping, facilities management, IT management, and fundraising as well as arranging two tours per year for 20-30 people. The work-load varies throughout the course of the year, with the most intense time being May-August. During the off season, (September-April), the organization has three employees (managing director and two part time artistic directors). From May-August that number increases to include 2-4 production personnel, actors and designers for each of four shows, additional office personnel, interns and volunteers.

Job Description

Fundraising

The managing director will be responsible for working with the board of directors, the artistic directors and independently to identify and solicit major individual donors ($5,000 and above). They will also be responsible for an annual campaign, currently raising approximately $25,000. The annual campaign has it’s major push in December at the end of the fiscal year, the managing director will assemble a mailing list, craft messaging and letters, send direct mail and email and post to social media. In partnership with the board of directors, the managing director will identify and solicit new corporate gifts. The managing director will research available grant funding, create a grants calendar and do all grant writing.

Arrange twice yearly tours to theatre cities (generally one North American City and London), this involves putting the tour together, either in partnership with a tour company or on their own, making sure that information about the tour is getting out to previous tour goers as well as audience members. Collecting information from all the travellers, collecting payment from all the travellers and making sure all the vendors get paid.

Finance

The managing director will be responsible for all day to day bookkeeping (accounts receivable, accounts payable, payroll, etc.) as well as oversight of the financial well-being of the organization, including cash flow. In partnership with the artistic directors, the managing director will manage the expenses of the organization as well as all HR duties, including hiring. The managing director will provide the board of directors with regular reports on the fiscal health of the organization.

Work with Actors’ Equity and United Scenic Artists to insure proper contracting, payment and oversight of compliance with contracts.

Marketing/Box Office/Front of House

Plan and implement the marketing for a season subscription campaign and single ticket campaigns for four shows. This includes email blasts (Constant Contact), advertising, social media, poster and postcard distribution, etc.

Maintain website.

Using Ovation (Audience View) software, build a subscription season and single ticket houses. Oversee on-line, phone and in person ticket sales.

During the 12 week summer season, staff front of house (box office, house management, ushers and concessions) for each performance.

Other

As with any small arts organization, the managing director will be expected to be flexible. Duties and responsibilities may come up that are not covered in this job description. The theatre owns two houses that house artists and interns during the season. The maintenance and repair of these is the responsibility of the managing director (with contractors doing the work). The theatre also takes responsibility for the maintenance and repair of three rental facilities, including our rehearsal rooms, the theatre itself and our rented office space. All spaces require internet access which is overseen by the managing director.

Qualifications

Previous theatre administrative experience

Excellent written and spoken communication skills

Experience with some or all of the following software: Microsoft Office, Google Workspace, Ovation (Audience View), Quickbooks, Constant Contact and WordPress

Commitment to working with and creating community

Commitment to anti-racism and equity, diversity and inclusion

Driver’s License and Car

Compensation

This is a year round full time job. The expectation is that the managing director will be available to work evenings and weekends during the 12 week summer season and as needed during the rest of the year. As such, the schedule can be somewhat flexible outside the summer season.

Salary $60,000

To apply, please send cover letter and resume to info@Chestertheatre.org