Executive Director

Executive Director

SpeakEasy Stage – Boston’s home for bold theatre – invites applications and inquiries from theater professionals interested in providing strategic and collaborative leadership in the inaugural role of Executive Director.

Who are we?

In 1992, SpeakEasy Stage was born with a simple idea – to give emerging, local artists a chance and build a thriving theater scene in Boston. From its humble 40-seat beginnings to its 200+ intimate blackbox spaces at the Calderwood Pavilion, it has grown into a leading voice in Boston’s thriving theatre ecosystem. SpeakEasy’s driving force – which lies at the heart of its programming, administration, and board leadership – is its unrivaled commitment to boldness. Driven by a relentless calling to leverage the transformative power of theatre to connect us with ourselves and each other, it produces – and supports the development of – vital, timely stories that unearth the myriad of experiences, identities, and journeys that make us human. Its five-production mainstage season of contemporary plays and musicals and suite of curated community programs entertain us while being relevant and thought-provoking. It facilitates important conversations about truth, identity, longing, pain, heart, inspiration, self-confidence, and so many of the human emotions and values that we all wrestle with every day. Its work addresses complex, multifaceted themes – such as gender identity and acceptance, immigration histories and policies, and racial power imbalances – with courage, compassion and authenticity on stage and off. It champions emerging and diverse voices and dives bravely into the depths of our society’s complexities, playing an important role in compelling essential community dialogue and ultimately, social change. Its shows have been known to spark conversations and introspections that continue months, and even years, after leaving the theater. As critics and patrons have described:

“Speakeasy Stage Company’s Production of the inheritance is as perfect and vital as it gets. i’ll be thinking about this play for the rest of my life.” christopher ehlers, digboston

“every speakeasy show i see stays with me. you’re doing the important work of showing us theatre that matters.” – Audience Member

SpeakEasy’s evolution and success have been dually driven by the visionary and humanistic leadership of its founder and Producing Artistic Director, Paul Daigneault, and by its talented community of Boston-based artists, creative and production teams, and administrators who consider it a home for artistic risk-taking and civic impact. SpeakEasy benefits from a committed Board of Directors, each of whom are deeply engaged in the life of the organization and provide the strategic, intentional leadership that enables it to thrive. The Company has a demonstrated track record of investing in its people – from emerging talent and future arts leaders to its community of accomplished professionals, patrons, and donors. This investment is underscored in its active equity, inclusion and belonging initiatives being collectively advanced by its staff, Board, artists, and creative and production teams.

What’s next?

For over thirty years, SpeakEasy has been led by its founder and Producing Artistic Director Paul Daigneault. In recent years, Daignault and the Board of Directors have been envisioning SpeakEasy’s impactful future, which will include a focus on efficient and innovative business operations, an amplified community engagement effort and a diversified philanthropic effort. Recognizing that both the artistic and managerial roles have increased in scope and complexity as the Company has evolved, Daigneault and the Board have designed a new leadership role which will split the artistic and management responsibilities and support SpeakEasy’s next stage of growth and evolution. At this important juncture, SpeakEasy invites interest from theater professionals who have a vision for furthering this important institution as its inaugural Executive Director.

In line with its mission, SpeakEasy welcomes inquiries from all interested candidates and strongly encourages individuals identifying as BIPOC, LBGTQIA+, neuro-diverse, and differently-abled to consider the opportunity, as well as individuals who meet some, but not all, criteria and bring relatable experience that they feel would prepare them to excel in the role.

Who are you?

The Executive Director is a new position which will lead SpeakEasy’s management strategy and operations and serve as a trusted partner and collaborator to its Producing Artistic Director and its Board of Directors.

They will be a passionate and engaging theatre professional, driven to tell bold stories, champion diverse voices, and expand SpeakEasy’s impact. They will be a relationship builder at their core, committed to building trusting relationships with artists, staff, board members, audiences, donors, and Boston’s theatre community.

They will be a strategic business leader able to partner meaningfully with the Producing Artistic Director, Board of Directors, and staff to operationalize the artistic vision and produce the resources, organizational structures, and visibility necessary to achieve it.

They will bring the ability and enthusiasm to develop engaging marketing and fundraising strategies that celebrate and amplify its distinct contribution and generate diversified portfolios of earned and contributed revenue. They will be an effective storyteller able to articulate a compelling case for support for the Company’s productions, programs, artists, outreach, and impact.

They will be a collaborative and inclusive leader with an interest in advancing its equity, inclusion and belonging practices in partnership with the Artistic Director, Board, staff, artists, creative and production teams, and consultants. They will bring an ability to reflect on their lived experience and collaborate with the Board, staff, artists, directors, designers, and community partners with lived experiences different from their own.

Please read more about SpeakEasy’s equity, inclusion and belonging initiatives here.

Who will you be working with?

The Executive Director and the Producing Artistic Director dually report to SpeakEasy’s Board of Directors and this trio leads the organization. Read about SpeakEasy’s staff and Board here. 

Direct reports to the Executive Director are the Director of Marketing and Communications, the Director of Development and a supporting business role (such as a General Manager or a Business Manager). The first two positions are currently filled by talented staff members. Acknowledging this leadership change, the supporting business role role will remain unfilled to allow the incoming Executive Director the freedom to design and hire this supporting position based on their expertise and needs. 


  • In partnership with the Artistic Director and Board, implement a strategic direction that aligns mission, strategy, and outcomes in pursuit of artistic excellence, community engagement and operational strength. Enrich SpeakEasy’s existing strategic direction and review and realign annually.
  • Oversee the organization’s marketing and fundraising efforts, assuming lead responsibility for earned and contributed revenue streams of approximately $2 million annually.
  • Direct, support, and partner with the Director of Marketing and Communications to design and implement strategies to build earned revenue from ticket sales, subscriptions, and other means.
  • Direct, support, and partner with the Director of Development to cultivate, solicit, and steward existing major donors and institutional and government funders, and prospect new ones. Partner with the Development Committee of the Board in these efforts. 
  • Serve as a leading representative of the organization in the community and support other artists and staff who also wish to represent SpeakEasy. Build trusting relationships with press, donors, volunteers, and collaborators. Prospect, steward, and enrich partnerships with community organizations in partnership with SpeakEasy’s staff. Represent SpeakEasy nationally in industry networks. 
  • Build trusting, productive relationships with board members that maximize their time, talent and expertise to advance SpeakEasy’s mission and goals. Oversee methods for tracking progress on operational and financial goals throughout the season and report to the Board on a regular schedule. Serve as an ex officio member of the Board and coordinate and attend all Board meetings. 
  • Oversee SpeakEasy’s annual operations and budget, in collaboration with the Executive Committee of the Board. Oversee the administration of production and operating budgets with support from the General Manager role. Provide oversight of all operations in accordance with SpeakEasy by-laws, policies, and the requirements of labor unions and employment laws. 
  • Reflect SpeakEasy’s culture of collaboration, team-building, mutual respect, and artistic advancement. In partnership with the Board, Artistic Director, staff, and creative and production teams, continue to advance and amplify the company’s equity, inclusion, and belonging goals. 
  • Attend occasional evening and weekend meetings and events, including Board meetings, fundraising events, and key programs that provide opportunities to engage SpeakEasy’s constituents. 

Preferred skills and attributes

  • 7-10 years of progressive management experience and a demonstrated ability to steer fundraising, marketing, and financial management efforts in the non-profit context 
  • Excellent interpersonal skills to lead, inspire and motivate within a multi-faceted organization. Collaborative and supportive approach to management. 
  • Ability to build trusting, productive relationships with board members, staff, artists, audiences, donors, and Boston’s theatre community. 
  • Excellent oral and written communications skills 
  • Mission-driven, strategic thinker, able to make thoughtful decisions when faced with competing priorities

Employment and Compensation

  • Salary: $115,000 – $125,000 
  • Start date: Negotiable, Approximately Spring/Summer 2023. 
  • SpeakEasy’s office is located in Boston’s South End at 551 Tremont Street; all staff have the option of working one day a week from home. 
  • Benefits: Health, dental, and disability insurance. 
  • Proof of full vaccination against COVID-19 is required (or proof of medical/religious exemption).

Our Equity, Inclusion, and Belonging initiatives

On stage and throughout our programming we tell stories that invite us to understand ourselves and the world around us more deeply, to uplift the voices of all races, ethnicities, gender identities and economic statuses. We believe live theatre truly can connect us to one another.

In 2020, SpeakEasy’s staff and Board came together with local consultant Deidra Montgomery to examine the company from top to bottom for opportunities to promote equity, justice, and belonging throughout its practices. Building on previous efforts in its 2016-2020 Strategic Plan and 2019 Cultural Competency framework, this team developed a detailed, multi-year plan that is designed to embed inclusionary practices in every step of its work. The plan and subsequent progress reports can be found here. Select advancements since beginning this work include:

  • Recruited and onboarded new board members resulting in a shift in the racial demographics of the Board from 7% BIPOC in 2020 to 29% BIPOC presently in 2023. The demographics of board, administrative staff, and creative and production teams are available here.
  • Contracted EDI Consultant Kira Troilo, of Art & Soul Consulting, on a retainer basis to serve as an ongoing resource in the rehearsal room and for SpeakEasy’s staff and Board. Expanded the role of its Community & Artistic Programming Manager to include time in rehearsals and performances to allow for direct connection between staff and artists to resolve concerns in real time and ensure a consistent culture in all SpeakEasy spaces.
  • Initiated organization-wide EDI training, with all members of the staff and Board completing training with Angela Park Consulting and the Cultural Equity Learning Community through Arts Connect International. Engaged Gender Inclusion Consultant, Shira Helena Gitlin, to build a training video and resource guide to ensure a shared vocabulary when entering a rehearsal room or meeting. Both trainings are now required of all new staff, artists, and board members.
  • Instituted a Cultural Consultant program, where first-voice individuals are hired for every show to serve as advisors to assure the story is authentically presented on the stage as well as in marketing and communications materials. These consultants further serve as stewards of community dialogue on the themes presented, playing a leadership role in talk backs and post-show discussions.
  • Developed Community Expectations Guidelines to include clear instructions on how to engage with one another and how to report any problems or challenges. This statement is displayed in the theater, in our programs, and on our website, and is reviewed with our equity plan at every first rehearsal.
  • Instituted Audio Description and Open Captioning for select performances of every production and sensory friendly performances for select productions.
  • Expanded the group of the people who are involved in the decision-making for season selection. Assembled a script reading committee, composed of artists and administrators from the Boston theatre community that is diverse in race, gender identity, age, sexual orientation, and socio-economic status to read scripts, discuss the viability and potential value of production, and inform SpeakEasy’s selection. All
    participants are compensated for their time.
  • Established surveys and polls for artists to provide feedback on their experiences, as well as optional exit interviews with SpeakEasy’s EDI consultant for artists to share thorough feedback on the rehearsal/performance environment. This feedback is used to monitor progress and identify opportunities for continued advancement.

These efforts are in progress as a collaborative initiative of the staff, Board, Artistic Director, artists and creative and production teams. This group is looking forward to inviting and incorporating the new Executive Director’s perspective, voice and lived experience into this work.

Does this opportunity intrigue you? Let us know!

This search is being facilitated by Syrah Gunning, Director, Executive Development and Brett Egan, President of the DeVos Institute of Arts Management at the University of Maryland, a leading provider of arts management services, training and thought leadership for arts, cultural, and educational sectors worldwide. Learn more here. 

To apply, please email your resume, a brief answer to the question below, and any questions you have about the opportunity to Syrah Gunning at segunning@devosinstitute.net. 

Why are you interested in this opportunity at this point in your career? What draws you to SpeakEasy’s work? 

Applications and inquiries will be reviewed on a rolling basis and will continue to be accepted until the position is filled. For priority consideration, please contact us by mid-March 2023. Inquiries or questions without resumes are also invited.

Read more about our work

SpeakEasy’s spirit is best understood through its production history, testimonials and images, which can be found throughout its annual reports and history here:

Reflections of its patrons, audiences, and community from the Annual Reports include:

  • “Every Brilliant Thing was such a moving, grounding experience. It changed something in me. I’ve never seen anything like it, and its message will stay with me for a long time.” – Audience member
  • “When else do you get to see a production about a Black woman that is completely humanizing? I’ve never felt so seen by a production.” – Audience member
  • “TJ Loves Sally 4 Ever crackles with freshness. It’s a hilarious, biting and sobering distillation of where society stands today.” – Jared Bowen, GBH
  • “While some of the material was challenging, the pain and humanity of each of the characters shines through … and challenging is what I expect from SpeakEasy. This is an important story … I’m glad you have told it in such a bold and engaging production! Bravo!” – Audience member
  • “One of my students who attended has severe autism, and according to the professionals that he works with, should be in a life skills program. His parents chose to send him to our public school. He is new to our school this year and is still making connections. On the bus ride to the theater, he sat alone. On the ride back, kids were empathizing with him, sitting with him, trying to get to know him. It was a beautiful moment.” – Noah Dawson, Drama Director and Special Education Instructor, The Sizer School, following a sponsored Student Matinee Series for local middle and high school students
  • “I organized a large group to see Small Mouth Sounds, and the reviews across the board have been glowing. Discussion around the show continues a week later as the characters permeate and themes percolate. A truly superb and lingering experience.” – Robby Morse Levy, SpeakEasy Board of Advisors
  • “I am really grateful to MassHousing and SpeakEasy Stage for the opportunity to see this play. It touched on some relevant issues, such as racism, colorism and self-love. I wish every young woman of color had a chance to see this play to explore the topics and know there are other young women around the world grappling with these same issues.” – Annie Russell, Participant in partnership with The Boston Foundation and MassHousing, which sponsored 150 residents of subsidized housing units to experience the play with their families
  • “SpeakEasy’s fellowship provided me with valuable insights into how a successful nonprofit theater must function: with kindness, heart, consciousness, immense dedication, and, above all else, the ability and willingness to say “yes.” SpeakEasy is a gift to the Boston theater scene and I could not be more thankful for their knowledge and trust.” – David Keohane, 2018-2019 Artistic Fellow
  • “I always felt seen, respected, supported, and valued by the company. It always felt like the company was really supporting the production and all of the actors involved. Everyone was really professional and wanted to produce high quality work, but also valued creating a safe environment for folks.” – Artist from the cast of Men on Boats
  • “I trust SpeakEasy to get the right people in the room, and to get the right voices for the story.” – Actor Exit Interview

A Lasting Gift

Please consider making a philanthropic gift to SpeakEasy Stage. Your donation will help us build and strengthen our community for the next 30 years.

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