Dawn Lepore

Lepore holds a BA from Smith College.⁠[1]

Lepore spent 21 years at The Charles Schwab CorporationThe Charles Schwab CorporationThe Charles Schwab Corporation is a financial services company headquartered in Westlake, Texas, United States, whose stock trades on the New York Stock Exchange (ticker SCHW). Through its subsidiaries it operates wealth management, securities brokerage, banking, asset management, and custody businesses, and it was founded by Charles R. Schwab in 1971.Open the full entry and Charles Schwab & Co., Inc., where her roles included chief information officer and vice chairman of technology, active trader, operations, business strategy, and administration; she was a member of Schwab’s executive committee and a trustee of SchwabFunds. She played a key role in Schwab’s e-commerce business.⁠[1][2]

From December 1999 to January 2013 Lepore served as a director of eBay.⁠[1]

In September 2004 the online pharmacy drugstore.com, based in Bellevue, Washington, named Lepore chief executive officer and successor to the retiring Peter Neupert as chairman. She took office in October 2004 and served until the company’s sale to Walgreen Co.WalgreensWalgreens is an American retail pharmacy chain founded in 1901 that offers prescription filling, vaccinations, health services and everyday retail goods. Its operating company, Walgreen Co., was formerly part of Walgreens Boots Alliance (WBA) and became an independently operated private company after Sycamore Partners completed its acquisition in 2025.Open the full entry in June 2011.⁠[2][1]

From April 2008 to June 2011 she served as a director of The New York Times Company.⁠[1]

From February 2012 Lepore served as a director of Quotient Technology Inc. From March 2012 to January 2013 she was interim chief executive officer of Prosper Marketplace, a privately held peer-to-peer lending marketplace. In October 2012 she joined the board of AOL Inc., serving until its sale to VerizonVerizonVerizon (Verizon Communications Inc.) is one of the largest telecommunications carriers in the United States, formed in 2000 through the merger of Bell Atlantic, one of the “Baby Bells,” and GTE. Headquartered in New York City, it operates a nationwide wireless network, Fios fiber broadband and communications services for businesses and government, and is listed on the New York Stock Exchange and Nasdaq.Open the full entry in July 2015.⁠[1]

In 2013 she joined the board of RealNetworks, serving on its compensation committee and chairing its nominating and corporate governance committee; from June 2013 to June 2014 she was also a director of The TJX Companies, Inc.⁠[1]The TJX CompaniesThe TJX Companies, Inc. is an American off-price retailer of apparel and home fashions whose businesses include TJ Maxx, Marshalls, HomeGoods, Sierra, Homesense, Winners and TK Maxx, with stores in ten countries on three continents.Open the full entry

On March 25, 2015, Andreessen HorowitzAndreessen HorowitzAndreessen Horowitz (a16z) is a venture capital firm founded in 2009 by Marc Andreessen and Ben Horowitz. It invests from the seed stage through the growth stage and provides operational support to its portfolio companies.Open the full entry (a16z) released the episode “a16z Podcast: Public or Private? Finding the Right Board Seat,” featuring Lepore, former chair and CEO of drugstore.com and a director of AOL, RealNetworks, and Coupons.com, alongside Zillow GroupZillow GroupZillow Group is an American online real estate marketplace company with its principal executive offices in Seattle, Washington, and Class A and Class C shares listed on Nasdaq. It announced the wind-down of its home-buying business Zillow Offers in November 2021, has been led by chief executive Jeremy Wacksman since August 2024, and in October 2026 agreed to pay $212.5 million in cash to settle an investor class action covering share buyers from August to November 2021.Open the full entry chief marketing officer Amy BohutinskyAmy BohutinskyAmy Bohutinsky is an American executive and investor who worked at Zillow from 2005 to 2019, serving as chief marketing officer and then chief operating officer. She is a director of Zillow Group and Duolingo and an operating partner for TCV funds.Open the full entry and former AmazonAmazonAmazon is a publicly traded U.S. technology and retail company founded by Jeff Bezos in 1994, with its principal corporate offices in Seattle. Its businesses span e-commerce, logistics and fulfillment, digital advertising, membership and entertainment services, consumer electronics, and Amazon Web Services cloud computing.Open the full entry general counsel Michelle Wilson.⁠[3]

All three guests were sitting board directors and veteran executives; the episode discussed why, when, and how to take a board seat and whether to focus on a public or private company. It was uploaded to the a16z YouTubeYouTubeYouTube is Google’s video-sharing and creator platform, founded in 2005 by Steve Chen, Chad Hurley, and Jawed Karim and acquired by Google in 2006. Built around video uploading, viewing, and creator earnings, the platform has developed Shorts, YouTube Music, Premium, YouTube TV, and products for children, and is headquartered in San Bruno, California, United States.Open the full entry channel on January 1, 2019.⁠[3][4]