Pioneering Small Business Software & Empowering Entrepreneurs w/ Gail Goodman, Founder & CEO of Constant Contact

In this episode of Outsider Inc., host Ian Hathaway interviews Gail Goodman, former CEO of Constant Contact. Goodman discusses her journey from her early entrepreneurial endeavors to leading Constant Contact from startup to IPO and ultimately to a $1.1 billion acquisition. She emphasizes the importance of execution over ideas and how a deep commitment to small businesses shaped her approach to building and scaling a SaaS company. She also reflects on the emotional transition after 17 years as CEO and her ongoing work supporting underrepresented entrepreneurs.

Show Notes:

(02:57) Childhood Entrepreneurial Roots

(06:59) Seeing Dysfunction Up Close and Learning What Not to Do

(08:03) The Leap to Leading Constant Contact

(12:09) Overcoming Imposter Syndrome and Building a CEO Peer Network

(18:59) Customer Research and the Art of "Following Them Home"

(21:13) Cracking Conversion and Retention in Early SaaS

(30:57) Preparing for an IPO and Leading Through Rapid Scale

(33:40) Public Company Pressures and Cultural Shifts

(36:00) The Emotional Reality of Transitioning Out of the CEO Role

(38:14) Joining Boards and Rethinking Leadership from a New Seat

(44:10) Being an Outsider in Tech and Venture Capital

(47:30) "People Gut" and the Art of Hiring Well

(51:55) Supporting Underrepresented Entrepreneurs Through EforAll

(54:00) Beyond the Bio: Gail Goodman

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Gail Goodman, Founder & CEO of Constant Contact

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.

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