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Rob Chesnut

General Counsel + Author + Speaker

Rob Chesnut is a general counsel, trust and safety pioneer, prosecutor, author and keynote speaker on the subject of growing business through a focus on integrity. He left Airbnb in 2021 after over 5 years as the company’s General Counsel and Chief Ethics Officer, and was recognized as one of the Financial Times Global 25 General Counsels. Airbnb, Inc. is a $100 billion public global travel and payments company that operates an online marketplace and hospitality service for people to rent short-term lodging including homes, apartments and rooms, and to participate in local experiences. The company has over 7 million lodging listings in over 100,000 cities and 191 countries and has facilitated over 500 million guest check-ins.

Rob is a graduate of Harvard Law School and the University of Virginia. He worked for 14 years with the U.S. Justice Department, including 10 years as an Assistant United States Attorney in Northern Virginia. As a federal prosecutor, Rob ran the Major Crimes Unit and prosecuted an array of bank robberies, kidnappings, murder, and drug trafficking cases. He handled the prosecution of CIA, FBI and other employees of the intelligence community for espionage, including CIA employee Aldrich Ames. He is the recipient of the Justice Department’s John Marshall Award for litigation and the CIA’s Outstanding Service Medallion.

In 1999, Rob left the U.S. Attorney’s Office and moved to California to become eBay’s third attorney, handling litigation, IP and regulatory/compliance matters for the company globally. Rob was promoted to run the company’s North American legal division in 2001, and in 2004 he was promoted to eBay’s executive leadership team as Sr. Vice President of a newly created Trust and Safety department. As the founder and head of eBay Trust and Safety, the internet’s first marketplace trust and safety department, Rob was responsible for overseeing all site rules and policies for the eBay global community of over 150 million users. Rob’s team built eBay’s fraud detection and prevention infrastructure, reduced reported fraud and counterfeiting activity on eBay’s 20+ sites by 60% over 4 years. He appeared on the Oprah Winfrey Show as a safe internet shopping expert in 2006.

In 2010, Rob joined Chegg as its first general counsel. Rob set up Chegg’s legal department, and as a member of the executive team helped take the company public and transform it from a physical textbook rental site to a multi-service digital learning platform.

Rob joined Airbnb in the spring of 2016, where he grew the legal team from 30 to over 150 legal professionals in 20 offices around the world. His team led initiatives to promote home sharing and address regulatory issues with local governments and landlords around the world. Rob developed a popular interactive employee program, Integrity Belongs Here, to help drive ethics throughout the culture at the company. His book “Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution” was published by St. Martin’s Press in July 2020.

Rob has served on a number of advisory boards for internet marketplace startup businesses, including Uber, Upwork, Turo, and Poshmark. He lives with his wife and children in the San Francisco Bay area.

Rob is a keynote speaker on organizational integrity, and he works with companies to help them develop strategies to drive integrity into their culture. He writes a column called Good Counsel for Bloomberg Law and teaches a class on Tech and Ethics at Northwestern University. He can be reached at www.intentionalintegrity.com.

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