Dan Rosensweig
Photo: JD Lasica from Pleasanton, CA, US, CC BY 2.0, via Wikimedia Commons33

Dan Rosensweig

American business executive

Dan Rosensweig is an American business executive who is chairman, president and former chief executive officer (CEO) of student services company Chegg. Previously, Rosensweig served as president and CEO of Guitar Hero; COO at Yahoo!; president of CNET, and president and CEO of ZDNet.2

From Wikipedia’s article on Dan Rosensweig (this version), CC BY-SA 4.0.

Companies

  • Rent The RunwayBoard member Oct 26, 2021 to now10
  • CheggChair Nov 12, 2013 to now11
  • AdobeBoard member Jan 12, 2009 to now12
  • CheggChief executive officer Feb 2010 to Jun 4, 202413
  • CheggPresident Nov 12, 2013 to Feb 4, 201911
  • Time Inc.Board member Jul 6, 2017 to Jul 6, 201714
  • AltabaChief operating officer Jan 5, 2006 to Apr 3, 200715

Holdings

Stock this person has reported owning, from the forms officers and directors file with the SEC. See the biggest insider stakes.

Shares held

  • Chegg CHGG7,652,283 shares16$5.9M at $0.77Sep 15, 2026
  • Adobe ADBE19,934 shares17$5.1M at $254.63Apr 17, 2026
  • Rent The Runway RENT57,357 shares18$102.1K at $1.78Aug 13, 2026

As of each latest filing. The line shows shares held over time.

Recent filings

  • Sep 12, 2026Shares withheld for tax 6,337 shares at $0.73 of Chegg16
  • Aug 11, 2026Granted 35,481 shares of Rent The Runway18
  • Jun 12, 2026Shares withheld for tax 6,337 shares at $1.11 of Chegg19
  • Jun 12, 2026Sold 6,337 shares at $1.11 of Chegg20
  • Jun 12, 2026Shares withheld for tax 1,956 shares at $1.11 of Chegg19
  • Jun 12, 2026Sold 1,956 shares at $1.11 of Chegg20
  • Apr 15, 2026Exercised options 900 shares of Adobe17
  • Mar 12, 2026Shares withheld for tax 7,004 shares at $0.57 of Chegg21
  • Feb 13, 2026Bought 100,000 shares at $0.56 of Chegg22
  • Dec 16, 2025Granted 16,759 shares of Rent The Runway23
  • Dec 12, 2025Shares withheld for tax 6,337 shares at $0.92 of Chegg24
  • Nov 17, 2025Granted 3,850,000 shares of Chegg25
  • Nov 17, 2025Granted 1,650,000 shares of Chegg25
  • Sep 12, 2025Shares withheld for tax 6,337 shares at $1.54 of Chegg26
  • Jul 8, 2025Granted 1,685 shares of Rent The Runway27
  • Jun 12, 2025Shares withheld for tax 1,956 shares at $1.47 of Chegg28
  • Jun 12, 2025Shares withheld for tax 50,696 shares at $1.47 of Chegg28
  • Apr 22, 2025Exercised options 633 shares of Adobe29
  • Mar 12, 2025Shares withheld for tax 1,778 shares at $0.86 of Chegg30
  • Mar 12, 2025Shares withheld for tax 4,595 shares at $0.86 of Chegg30
  • Mar 12, 2025Granted 16,272 shares of Chegg30
  • Dec 12, 2024Shares withheld for tax 2,582 shares at $2.24 of Chegg31
  • Dec 12, 2024Shares withheld for tax 6,532 shares at $2.24 of Chegg31
  • Sep 12, 2024Shares withheld for tax 2,582 shares at $1.85 of Chegg32
  • Sep 12, 2024Shares withheld for tax 6,533 shares at $1.85 of Chegg32

Early life and education

  • Date not recordedHobart and William Smith Colleges3
  • Date not recordedScarsdale High School3

Career

Occupation: business executive.7

  • Since 2010Chief executive officer, Chegg4 5
  • Since 2009Board member, Adobe6

Following college, Rosensweig's first job was at Dictaphone, then an independent subsidiary of Pitney Bowes, selling word processors door-to-door in Manhattan. Within three hours on the job, he was informed that the company had to lay off nearly 1,000 people, including his division.

In 1983, Rosensweig began working at Ziff Davis as a cold caller selling magazines to mom-and-pop computer retail stores, then worked his way up through the circulation department, to classified ad sales and display ad sales, and then to associate publisher of PC Magazine. Under Rosensweig's leadership, PC Magazine became the leading computer magazine in both audience reach and revenue.

In 1996, Rosensweig led the Ziff Davis launch of a series of Internet print magazines, including, by license, the acclaimed Yahoo! Internet Life. In 1998, he took over Ziff Davis' Internet Operation as president and CEO of ZiffNet, now known as ZDNet, where he took the company public and sold it to CNET, in 2001. Rosensweig played a critical role in the successful merger with CNET. During his tenure at CNET, Rosensweig served as a key participant in company-wide efforts to develop and introduce innovative new Internet advertising formats, such as interactive messaging.

In 2002, Rosensweig joined Yahoo! as COO, where he oversaw global operations through 2006, and developed a mentoring program.

In 2007, Rosensweig became a partner of private investment firm Quadrangle Group, founded by Steven Rattner, opening an office in Silicon Valley.

In March 2009, Rosensweig became president and CEO of Guitar Hero; under his management, the company launched Band Hero and DJ Hero.

In February 2010, Rosensweig joined Chegg as president and CEO, where he has overseen expansion and multiple acquisitions, and heads operations and executive management. He launched the company's IPO in 2013. Chegg expanded from textbook rental into a portfolio of student services under his leadership, transforming Chegg's digital assets to meet student needs.

In June 2024, Rosensweig stepped down as CEO of Chegg, and was succeeded by Nathan Schultz.

Rosensweig is a proponent of mentoring, and of workplace equality. He is an investor in many Silicon Valley companies, including Rent The Runway and Reputation.com.

From Wikipedia’s article on Dan Rosensweig (this version), CC BY-SA 4.0.

Personal life

  • BornDobbs Ferry8
  • CitizenshipUnited States9

Rosensweig is Jewish, and grew up in the same New York neighborhood as Mark Zuckerberg. He has two daughters with his wife Linda.

From Wikipedia’s article on Dan Rosensweig (this version), CC BY-SA 4.0.

Sources

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    SEC EDGARChegg, Chair
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    Wikidata and SEC EDGARAdobe, Board member
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    Wikidata and SEC EDGARChegg, Chief executive officer
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