about us

why we do what we do

“My core values of integrity, authenticity and decency inform my work to reimagine a more just, equitable and sustainable theater landscape. Right now, our society and the theater field face challenges like no other in modern history. This moment demands profound transformation. Through My Purple Crayon Advisors, I will serve values-driven organizations looking to remake themselves to better serve their communities and impact the field.”

—Founder and My Purple Crayon Advisors principal Harold Wolpert

“service is the rent that you pay for room on this earth.”

—Shirley Chisholm

about harold wolpert

Arts leader and My Purple Crayon Advisors founder and principal Harold Wolpert (he/him) is a three-time Tony Award–winning arts executive with more than 30 years of experience and longtime leader, producer and manager at major not-for-profit theater companies. He is one of the most respected and passionate leaders in the field who works tirelessly to enact change, uplift artists and guide arts organizations forward.

Harold has served in leadership roles and made significant contributions to the advancement of some of the nation’s most prestigious not-for-profit theater organizations, including Signature Theatre, Roundabout Theatre Company and Manhattan Theatre Club.

Harold is actively engaged as a teacher, mentor and volunteer. Currently he is on the faculty of the David Geffen School of Drama and has a long history of leading and volunteering for organizations serving the LGBTQ community.

“look, i made a hat
where there never was a hat.”
—Stephen Sondheim

Inspired and motivated by the creativity of artists, the dedication of arts workers and mission-driven arts organizations, Harold has worked alongside preeminent theater artists at every stage of creative development on more than 250 Broadway, Off-Broadway and LORT productions, including three Pulitzer Prize and five Tony Award–winning productions and numerous national and international tours.

Most recently, while leading Signature Theatre, Harold steered and stabilized the company through a major transition and significant financial challenges. He articulated and activated a vision for Signature’s future advancement, which mobilized leading foundations and major donors to contribute multi-million dollar transformative gifts. Harold steadied the company through the COVID-19 pandemic. He leveraged his extensive network of producers to engineer new co-production and touring opportunities and create new revenue streams and produced the first cast recordings in Signature’s history. He spearheaded the company’s board growth by 50%. Harold created Signature’s first Equity, Diversity, Inclusion and Accessibility Committee, coordinated an all-encompassing EDIA action plan and charted a course for Signature to become a more inclusive, anti-racist organization.

As principal of My Purple Crayon Advisors, Harold served as a Strategic Consultant for Signature Theatre and Interim Managing Director of McCarter Theatre Center. Additional clients have included, among others, Roundabout Theatre Company, Goodspeed Musicals and Ford’s Theatre.

Originally from Philadelphia, he lives in Brooklyn with his partner and their black cat, Joey, who occasionally serves as his (unreliable) assistant.

what they say

“You see, Harold Wolpert isn’t really Management. He’s an artist pretending to be Management. He’s as much in love with plays and actors and playwrights and the whole crazy process as you and I are. It’s just that someone has to play the Bad Cop in the theater in order for good stuff to happen in the theater and Harold plays that role more brilliantly, more compassionately—and with more of a vision for the future—than anyone I can name. Actors adore him and directors don’t turn and run when they see him. He has a keen mind and a huge heart. He is a rock for artists.”

—Terrence McNally, Playwright, Librettist and Screenwriter

“Harold is a very talented leader and manager who has a tremendous depth and breadth of knowledge and skills, including budget, financial and operational expertise. Harold also has significant experience with board engagement. As a member of the board, I worked closely with him on strategic planning and in a number of other capacities for Roundabout and always found him to be thoughtful, thorough and a problem-solver. As an executive leader at Roundabout, he played an integral role in identifying strategies and new sources of revenue to secure a stable future for the company. Harold is a top notch not-for-profit leader and executive.”

—Maureen Hayes, Roundabout Theatre Company Board Member

“Harold is a unique and visionary leader who combines clear-headed direction and focus on creating and executing strategy. His strong interpersonal skills and his commitment to organizational and individual staff development embody his core beliefs of compassion and integrity in all that he does. He is both beloved and deeply respected by colleagues and staff alike.”

—Susan Reilly Saldago, Founder, Hospitality Quotient

“Harold is a widely respected leader in the not-for-profit professional theater. He has wide ranging experience in all areas related to producing world class theater and managing complex institutions. Harold is extremely intelligent, empathetic, strategic and a good partner. ”

—Victoria Bailey, Executive Director, Theatre Development Fund

production history