The Leadership Dance — Episode 37

Championing Women's Voices, with Jenna Segal
Host: Alissa Hsu Lynch | Date: March 16, 2026

Episode Overview

This episode explores the dynamic career and mission of Jenna Segal—Emmy, Tony, and Clio award-winning producer and founder of Gatherer Enterprises—as she discusses her path from broadcast journalism to Broadway and her passionate commitment to amplifying women’s voices in arts and business. Host Alissa Hsu Lynch and Jenna Segal share personal stories about risk-taking, balancing ambition with authenticity, and reshaping history by elevating women's stories.

Key Discussion Points and Insights

Early Influences and Career Beginnings

• Jenna's Roots (02:14–03:00)
  • Grew up in New Jersey, initially planning to become a corporate lawyer inspired by "LA Law."
  • Realized her love for fast-paced problem-solving environments during an internship at CNN, prompting a shift to media production.
  • Quote:
    “I realized how much I love being on my feet, how much I love being able to react and problem solve quickly. And producing really fit that for me.” – Jenna Segal (03:00)
• First Steps in Media (04:05–05:54)
  • Secured a CNN internship after a serendipitous meeting with Dana Bash.
  • Learned the value of structure and energy at CNN, then interned at a law firm before fully committing to media.
• MTV Era and Pioneering Moves (07:04–08:39)
  • Got her break at MTV by emailing her resume—one of the first to leverage digital (email) applications.
  • Produced pilots during MTV’s explosive creative period, then moved back east after 9/11.

Transition to Theater & Production

• Nickelodeon & Production Skills (08:46–11:11)
  • Produced interstitial shows like "You Pick Live," learning improvisation and live production skills.
  • Value of adaptability:
    “I learned a tremendous amount...they asked me to come over and be a line producer...then decided to leave and have my first child and I was going to retire, which you can see how well that went.” – Jenna (11:09)
• Entering Broadway (11:38–13:35)
  • Shifted to theater production while raising young children; produced "Gigi," which began at the Kennedy Center and eventually made it to Broadway starring Vanessa Hudgens.
  • Real-world timelines:
    “Eight to ten years is really typical [to produce a Broadway show]. And that was for something where the music was written.” – Jenna (13:12)

Advocacy for Women's Voices

• Empowering Women in the Arts (15:25–17:29)
  • Founded Gatherer Enterprises to prioritize female-led projects after observing the paucity of women in theatrical decision-making, especially when the majority of ticket buyers are women.
  • “I want at least one woman in a decision-making situation...when it’s something geared to women. My focus isn’t that I want no men, I just want at least one woman at the table.” – Jenna (22:46)
• Difference Between Tokenism and True Representation (24:28)
  • Asserts importance of visibility and entry points:
    “Having a woman’s name on a list...it’s at least a starting point for investigation. If women don’t exist in the history books...you need a place where someone like me is like, ‘Ooh, I never heard about this person before’ and has the curiosity to maybe want to rediscover them."

The 31 Women Project & Art Collecting

• Rediscovering Lost Histories (17:32–21:08)
  • The "31 Women" initiative—her privately built collection inspired by Peggy Guggenheim's pioneering 1943 women's exhibition.
  • Jenna’s office is in Peggy's former gallery; she actively tracks down art by the original 31 women featured.
  • “I’m also personally working on a book about my experience of collecting—a collector and really knowing nothing...Peggy says she became her own best expert, and I would say she really taught me how to allow myself to be my own best expert and be okay with saying that out loud.” – Jenna (21:12)

Leadership, Challenges, and Values

• Facing Criticism for Centering Women (31:31, 22:35)
  • Admits to facing negative reactions but defends the mission with clarity and personal conviction.
  • “My deciding to support women is not a judgment that you are deciding not to…it helps me sleep at night. Because entertainment is an extremely risky business...if I’m going to lose money, I want to know that one more woman’s name has moved forward.” – Jenna (23:09)
• Leadership Skills & Boundaries (28:03–30:22)
  • Shares her approach to leadership: honesty, kindness, and hard boundaries when projects exceed her capacity.
  • Mentions founding the Heidi Thomas Initiative to foster script development for women playwrights.

Memorable Quotes & Moments

• "Just do it. Just go for it." – Jenna Segal, on taking career risks (07:35)
• “We were doing this live talk show in a room...probably about the size of this studio right now, five days a week.” (09:33)
• “I love to have a plan. And I always know that plan is never going to work. So you have to be able to improvise when the structure doesn’t support what you’re looking to accomplish.” – Jenna (26:08)
• When asked about a production mishap:
  “There was a dressing room incident where...the dressing room [for a celebrity] was in shambles. And I improvised by grabbing my assistant and running to TJ Maxx and basically buying it out and redecorating it.” (27:12)
• “No regrets. I really feel that whether it’s my anxiety or my worry or whatever it was, it got me to where I am right now in my career. And where I am right now, it really feels like where I should be.” (32:49)

Notable Timestamps

• 02:14 — Jenna on her childhood and career expectations
• 04:05 — CNN internship and early work ethic
• 07:35 — First big break at MTV
• 11:38 — Transition to Broadway producing
• 13:12 — Length of Broadway show production cycles
• 15:35 — Why elevating women’s stories matters
• 17:45 — The 31 Women project origins
• 21:12 — Lessons in collecting and self-teaching
• 22:35 — Handling criticism for women-centered focus
• 24:28 — The importance of writing women into history
• 28:03 — Leadership style and managing capacity
• 30:27 — The future of theater and arts
• 32:49 — Advice to her younger self, “No regrets.”

Quickfire Round (25:18–27:04)

• Coffee or cocktail? “I can make it without the cocktail. I can’t make it without the morning coffee.”
• Broadway or off Broadway? “Broadway.”
• Woman artist to know now? “Shihota Chiharu...she does this unbelievable work with red string where she just transforms spaces.”
• Structure or improvisation? “Improvisation.”
• Describe yourself in one word: “Tenacious...and generous.” (Prompted by Alissa)
• Favorite music to dance to: “Definitely 80s and 90s alternative.”

The Future of Theater (30:24–32:40)

• Predicts more rule-breaking, innovative formats (e.g., “Six,” “Hamilton”) as the industry responds to economic realities and creative opportunities.
• Notes the rising difficulty in the U.S. with production costs, especially due to healthcare, leading to more work originating abroad.

Conclusion

Jenna Segal’s journey is a masterclass in courageous improvisation, purposeful advocacy, and steadfast dedication to women’s voices in the arts. By candidly sharing her path—from refusing to settle for the expected to assembling a game-changing art collection—she encourages listeners to claim space, take risks, and keep history inclusive. For listeners seeking inspiration to choreograph their own leadership dance, this episode provides both practical wisdom and lasting encouragement.