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About Courtney Dickey, CLO

Courtney Dickey is the Chief Legal Officer of ZenBusiness. She leads the legal, procurement, and risk functions, as well as day-to-day people operations. Courtney brings more than 15 years of in-house legal experience across the technology sector, with deep expertise in corporate governance, regulatory matters, enterprise risk, transactions, and organizational scale.

Courtney Dickey, CLO
Courtney Dickey, CLO

Courtney Dickey is the Chief Legal Officer (CLO) of ZenBusiness


At ZenBusiness, Courtney builds the systems, practices, and culture that allow the company to scale with discipline. In addition to leading legal strategy, she has strengthened how the company manages performance, plans compensation, handles promotions, and engages employees. Her leadership combines legal expertise, operational judgment, and a people-centered approach to building organizations that perform and endure.

Courtney has advised and led major transactions across multiple venture-backed companies, including Dosh’s acquisition by Cardlytics, HomeAway’s acquisition by Expedia, and Opcity’s acquisition by News Corp. She brings a business-oriented approach to legal leadership that connects rigorous compliance with the day-to-day realities of building and growing a company.

Courtney’s results-driven leadership has been instrumental in managing significant financial transactions, including ZenBusiness's $205 million Series C fundraising. Her ability to manage complex legal and financial operations has driven growth and achieved key business objectives​.

Courtney’s Thought Leadership, Recognition, and Public Contributions

  • Chief Legal Officer since May 2023 (SVP & General Counsel 2021–2023); oversees legal, procurement, risk, and people operations. 
  • 15+ years of in-house tech legal experience, including roles at Expedia/HomeAway, then as first General Counsel at Opcity, and later as Chief Legal & People Officer at Dosh. 
  • Advised and led M&A across HomeAway’s acquisition by Expedia, Opcity’s acquisition by News Corp, and Dosh’s acquisition by Cardlytics.
  • Led the legal side of ZenBusiness’s $205 million Series C fundraising. 
  • Featured on CNBC’s “Now We Know! with Steve Guttenberg” (June 20, 2026) alongside CEO Ross Buhrdorf and fellow execs, spotlighting ZenBusiness’s AI platform. 

In the Media: Courtney Dickey + ZenBusiness in Public Conversation

PRESS

Austin pros in the running for Women in Business Awards

June 2026

PRESS

ZenBusiness Featured on "Now We Know" with Steve Guttenberg

June 2026

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ZenBusiness Team

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Email us at press@zenbusiness.com