Welcome to the Arena podcast

Cindy Hess, Partner at Fenwick – Big Tech's Big Deals: Counseling the world's most influential technology companies

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Even the most ingenious technologies won't go far without a solid legal foundation and a forward thinking framework that will help it scale,  and this episode's guest knows all about that. Cindy Hess is a corporate partner at Fenwick and for over 10 years she's served as the co-chair of the firm's startup and venture capital group. 

Over the course of her practice, Cindy has counseled technology companies on a broad range of corporate transactional matters. She's worked with a wide range of high tech clients including some of the hottest and most innovative companies in mobile SaaS and social media.
Cindy has had numerous industry honors, including being named as one of the Recorder's Top 10 Most Trusted Corporate Counselors, and one of the Top Women Leaders in Tech Law. She was also named to the Legal 500's Hall of Fame of the Venture Capital and Emerging Companies category. Cindy was the recipient of the Women in Business Law Award for Best in Technology, and the Silicon Valley Business Journal named her as one of the leading women of influence in Silicon Valley. She's a member of the State Bar of California and of New York. She received her undergraduate degree from Princeton, and her J.D. from Cornell.

We sat down to talk about Cindy's incredible career working on some of the biggest deals in history, and what she sees for big tech deals in 2023 and beyond.


  • How Cindy got her start with Fenwick (3:24)
  • What Fenwick does and why it's different than other firms (4:14)
  • Cindy's client base (7:58)
  • The part of the practice that Cindy thinks is strongest right now (9:17)
  • How Cindy got into law (10:06)
  • Cindy talks about some of the biggest deals at Fenwick (11:19)
  • The deal that was most transformative for Cindy's career (13:21)
  • Cindy talks about her experience as a woman in this field over the length of her career (14:36)
  • Mentors that have helped along the way (15:27)
  • Cindy's predictions for capital markets in 2023 (17:08)
  • Cindy discusses the findings of the latest edition of Fenwick's Silicon Valley Venture Capital survey (19:20)
  • Cindy's advice to founders going through the early stages of development, and what to consider when going public (23:05)
  • What's next for emerging companies looking to grow their business (24:16)


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If you have questions about the show, or have a topic in mind you'd like discussed in future episodes, email our producer, [email protected].

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