Cynthia Clarfield Hess

650-335-7238
chess@fenwick.com
Partner
Corporate

Cynthia Clarfield
Hess

Cynthia Clarfield
Hess

Cynthia Clarfield
Hess

Partner
Corporate

Recognized as a leader in tech law for corporate and venture capital matters, Cindy invests in long-term relationships with startup founders and investors.

Cindy counsels some of the most innovative companies in the mobile, SaaS, social media, and internet spaces through critical phases of their lifecycle—from formation and launch, through key milestones, to eventual exit. She represents companies and underwriters in transactions, including complex financings, mergers and acquisitions, and public offerings.

Recognized by TechCrunch as one of the top attorneys working with startup companies, Cindy builds results-oriented business connections that become long-term relationships with both investors and company executives. She is energized by working with public companies and startups—like Cisco Systems, Fitbit, GitLab, Nextdoor, and Peloton—that are revolutionizing the way everyday users of technology interact with the world.

Cindy offers deep technology experience and a keen ability to see the “big picture.” Clients say she “always gives good direction and different points of view.” (Chambers, client testimonial)

Cindy is deeply engaged with the firm’s Israel practice. She is also a contributor to the firm’s Venture Beacon—a data-driven deep dive into the trends shaping today’s venture market.

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  • Represented 6Sense, a leading Account Based Orchestration Platform, powered by AI, in its $200M Series E, $125M Series D, $40M Series C, $20M Series B, and $12M Series A financing rounds, and its acquisition of Fortella
  • Represented Fitbit, the maker of wearable health-tracking devices, in its $732M initial public offering
  • Represented GitLab, a complete DevOps platform, in its $100M Series D and $268M Series E financing rounds, as well as its $800M initial public offering
  • Represented Madison Reed, a hair color products company, in its Series A through Series G financing rounds
  • Represented Navan, an end-to-end travel management platform designed to offer complete corporate travel planning and support, in several successive multi-million-dollar financing rounds
  • Represented Nextdoor, a provider of private social networks centered around neighborhoods and communities, in several successive multimillion-dollar financing rounds and in its de-SPAC merger with Khosla Ventures Acquisition Co. II
  • Represented Peloton, the world’s largest interactive fitness platform, in several financings and in its $1.2B initial public offering
  • Represented Primary Kids, a New York-based children’s clothing brand, in its Series A through C financing rounds
  • Represented Rad AI, a healthcare company commercializing generative AI products, in its $60M Series C and $50M Series B financing rounds
  • Represented Schneider Electric in dozens of strategic investments
  • Represented SentinelOne, an autonomous cybersecurity platform company, in its $267M Series F and $1.4B initial public offering

  • Represented 6Sense, a leading Account Based Orchestration Platform, powered by AI, in its $200M Series E, $125M Series D, $40M Series C, $20M Series B, and $12M Series A financing rounds, and its acquisition of Fortella
  • Represented Fitbit, the maker of wearable health-tracking devices, in its $732M initial public offering
  • Represented GitLab, a complete DevOps platform, in its $100M Series D and $268M Series E financing rounds, as well as its $800M initial public offering
  • Represented Madison Reed, a hair color products company, in its Series A through Series G financing rounds
  • Represented Navan, an end-to-end travel management platform designed to offer complete corporate travel planning and support, in several successive multi-million-dollar financing rounds
  • Represented Nextdoor, a provider of private social networks centered around neighborhoods and communities, in several successive multimillion-dollar financing rounds and in its de-SPAC merger with Khosla Ventures Acquisition Co. II
  • Represented Peloton, the world’s largest interactive fitness platform, in several financings and in its $1.2B initial public offering
  • Represented Primary Kids, a New York-based children’s clothing brand, in its Series A through C financing rounds
  • Represented Rad AI, a healthcare company commercializing generative AI products, in its $60M Series C and $50M Series B financing rounds
  • Represented Schneider Electric in dozens of strategic investments
  • Represented SentinelOne, an autonomous cybersecurity platform company, in its $267M Series F and $1.4B initial public offering

  • 6Sense
  • American Express
  • AutoFi
  • Automattic
  • Cisco Systems
  • Fitbit
  • GitLab
  • GoPro
  • Hint
  • Impossible Foods
  • Impulse Space
  • Lovevery
  • Madison Reed
  • Nauto
  • Nextdoor
  • Pebble Mobility
  • Peloton
  • Prezi
  • Primary Kids
  • Rad AI
  • Rock the Bells
  • Schneider Electric
  • SendBird
  • SentinelOne
  • Shift5
  • SoloPulse
  • The Bot Company
  • WeMod

  • 6Sense
  • American Express
  • AutoFi
  • Automattic
  • Cisco Systems
  • Fitbit
  • GitLab
  • GoPro
  • Hint
  • Impossible Foods
  • Impulse Space
  • Lovevery
  • Madison Reed
  • Nauto
  • Nextdoor
  • Pebble Mobility
  • Peloton
  • Prezi
  • Primary Kids
  • Rad AI
  • Rock the Bells
  • Schneider Electric
  • SendBird
  • SentinelOne
  • Shift5
  • SoloPulse
  • The Bot Company
  • WeMod

“Cindy is very experienced. She is very strong, very smart and a great communicator.”

Chambers USA, 2022

“Cindy is very experienced. She is very strong, very smart and a great communicator.”

Chambers USA, 2022

“Cindy is very experienced. She is very strong, very smart and a great communicator.”

Chambers USA, 2022

Recognition Recognition Recognition

Recognition Recognition Recognition

Recognition
Chambers USA

2016 - 2024

Regularly ranks Cindy among the nation's leading lawyers for startups and emerging companies work (2016 – 2024), as well as in California for venture capital work (2018 – 2024)

TechCrunch

2019

Honored Cindy as the first attorney to be featured on its inaugural list of top startup lawyers.

The Legal 500

2019 - 2024

Highlighted Cindy as a "Hall of Fame" for venture capital and emerging companies.

U.S. News - Best Lawyers

2015 - 2021

Recognized Cindy as among The Best Lawyers in America for corporate and M&A law.

Lawdragon

2024 - 2025

Recognized Cindy as one of the 500 Leading Dealmakers in America.

Cindy’s work has brought her recognition from legal and business publications:

  • The Recorder named Cindy a Woman Leader in Tech Law (2013 – 2016), and named her one of Silicon Valley’s top 10 most trusted corporate counselors in its Trusted Advisors list (2016)
  • Silicon Valley Business Journal recognized Cindy on its Silicon Valley Women of Influence list (2016)
  • Daily Journal named Cindy among California’s Top Women Lawyers (2016)
  • Euromoney Legal Media Group recognized Cindy with the Women in Business Law Award for Best in Technology (2016)

Recognition
Chambers USA

2016 - 2024

Regularly ranks Cindy among the nation's leading lawyers for startups and emerging companies work (2016 – 2024), as well as in California for venture capital work (2018 – 2024)

TechCrunch

2019

Honored Cindy as the first attorney to be featured on its inaugural list of top startup lawyers.

The Legal 500

2019 - 2024

Highlighted Cindy as a "Hall of Fame" for venture capital and emerging companies.

U.S. News - Best Lawyers

2015 - 2021

Recognized Cindy as among The Best Lawyers in America for corporate and M&A law.

Lawdragon

2024 - 2025

Recognized Cindy as one of the 500 Leading Dealmakers in America.