Why Harold Wolpert Took the Leap to Signature Theatre

When you start out in the theater business as a young person (as I did), and remain in it for many years (as I have done), you find yourself in the fascinating position of taking stock not only of your own career, but also of the career arcs and inspirational ascensions of those with whom you’ve worked or known. One of those people who has worked in the trenches and risen through the ranks, all the while being a shining example of authenticity and pure dedication, is Harold Wolpert.

I’ve been acquainted with Wolpert for many years, going back to my time as a literary department intern at Manhattan Theatre Club when its administrative offices were located on the gritty far west side of Chelsea. Wolpert was serving as MTC’s company manager at the time. Those were the days before Sex and the City transformed the neighboring Meatpacking District into the trendy restaurant-and-nightclub Mecca it is today, the days when we all shared the sidewalk with pimps and prostitutes on our way to work. Colorful and thrilling times.

Wolpert has had a long and steady career since those MTC days, and he reached a new pinnacle after being selected as the new executive director of NYC’s Signature Theatre following a 10-year run as Roundabout Theatre Company’s managing director. But this wasn’t a direct transition. In fact, Wolpert left Roundabout in 2016 not knowing what the future would hold.

I spoke to Wolpert, one month into his new position to find out how things were going, why he stepped away from the industry and what about the siren song of Signature enticed him to return.

Robin Rothstein: What is your background? Did you study theater in college?

Harold Wolpert: I grew up outside of Philadelphia. I actually did not study theater in college — I majored in history at the University of Pennsylvania. However, I spent much of my time outside of classes as chairman and producer of Penn Players, a student run, professionally directed theater group at Penn.

RR: What was your first job in the theater?

HW: My first job was as company manager at Circle Repertory Theatre. It was there that I really learned about Off-Broadway theater, and how powerful it can be to work with other talented, passionate people on something we all care about. Part of what drew me to my current role at Signature was returning to the world of Off-Broadway.

RR: In which role over your career do you feel you’ve learned the most? Can you cite a specific teachable moment?

HW: I was at Roundabout for over a decade. It was there that I got to use the skills I had developed at Circle Rep, Manhattan Theater Club and [Houston’s] Alley Theatre to learn what it truly meant to be a leader of a not-for-profit arts organization. A lot was required of me in that job. I had to be particularly adept at managing complex challenges and move Roundabout forward, and lead the staff to reach their full potential. The teachable moment that stands out the most is one that is ongoing — those of us who are not artists should also work by the highest standards to match the quality and effort of the artists on the stages, and always remember that they and the plays that we produce must be the focus of all that we do.

RR: After Roundabout, did you expect to re-enter the theater industry in this kind of leadership role? What was your plan?

HW: I didn’t know exactly what my next move would be, but I knew that I love theater, so it’s not surprising that I ended up where I have. Signature has undergone a lot of transition in the past six years — first with its huge expansion, as it moved to the beautiful Pershing Square Signature Center, and then with the passing of its founder Jim Houghton. The company is in great artistic hands with Artistic Director Paige Evans (with whom I worked twice at MTC many years ago!) Given my experience in leading companies through transition, I feel confident my particular skill set is just right for the company at this time.

RR: Does theater have a duty to address divisive issues? Can it reach and impact those people with “alternative” points of view?

HW: Theater teaches us about the human condition — how people behave, how they change, how they communicate with each other. Throughout my career, I’ve been very active in the community, whether as a teacher, consultant, grants panelist or volunteer. These things go hand in hand for me — I believe we have a responsibility as citizens to be of service wherever and however we can. And we have a responsibility as artists and arts administrators to facilitate discussion and hold a mirror up to society. Signature brings people together at our Center, under one roof, to have a communal experience filtered through our own individual experiences and perspectives. But the important point is that we are sharing these moments.

RR: Besides featuring one playwright per season, what is Signature Theatre’s mission? 

HW: To celebrate playwrights and give them an artistic home. It’s a mission based in long-term relationships through three distinct residency programs that celebrate bodies of work, and provide writers with the resources to build bodies of work. We put the playwright at the center of the process. Everything is about context at Signature. That’s built into the design of the Center, where work is always happening in the context of other work, and a large community gathering space, with one entrance for artists, audiences and staff that makes everyone feel welcome. We are also very committed to accessibility, and are particularly proud of the Signature Ticket Initiative, which offers subsidized tickets at affordable prices to every production’s initial run.

RR: You’re 30 days on the job. What’s it like coming full circle and working with Paige Evans again?

HW: Amazing and overwhelming! I’m on what I’m calling a “listening tour,” just trying to get a sense of how things work here. No one else is doing what Signature is doing — it’s a really incredible place. The staff and the board care deeply about the mission and the work here. Paige and I have grown up in this industry together. It’s really exciting to get to partner with her at this point in my career.

RR: What do you hope to bring to your role as executive director?

HW: I’ve worked at amazing institutions in NYC and across the country, so I come to the table with some good experience under my belt. Signature is a special and beloved place, and I view my role to make sure it can continue to thrive and fire on all cylinders for many, many years to come.

RR: Any advice for mid-career arts administrators looking to make a change, but afraid to take the leap?

HW: Risk reaps reward. So does hard work, and being a decent human being. Be kind, keep your eyes open, and don’t be afraid to take chances, but always act with integrity and intentionality.