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|Founded||Chicago, IL (2000)|
|Headquarters||Chicago, IL, USA|
|Barry Metzger, CEO|
Number of employees
|423 (December 2009)|
|Parent||Charles Schwab Corporation|
- 2000 – optionsXpress founded by Ned Bennett, David Kalt and Jim Gray
- March 2003 – The company creates brokersXpress to serve registered representatives, financial planners and registered investment advisors
- 2004 – Inception of optionsXpress International, which expanded the company's offerings internationally
- 2004 – optionsXpress' services are extended to Australia
- 2005 – optionsXpress goes public with an IPO
- 2005 – The company begins offering its services in Canada
- 2006 – The company expands its offerings to Singapore
- 2006 – The company launches optionsXpress Europe
- January 2007 – optionsXpress acquires Xpresstrade, which increased optionsXpress' offerings to include over 300 futures products worldwide
- October 2007 – David Fisher becomes CEO (previously served as CFO)
- July 2008 – Acquisition of Paragon Futures/Open E Cry
- May 2009 – Acquisition Lanai Partners, LLC/Optionetics, Inc. This acquisition widened the breadth of optionsXpress' educational offerings, which now include workshops, classes (live and online), newsletters, DVDs and strategy support
- July 2009 – Launch of OX Mobile, allowing OX customers to monitor their accounts from their mobile phones
- May 2010 – optionsXpress launches Xtend, a downloadable and customizable platform that offers real-time streaming quotes, charts, and news on users’ desktops
- March 21, 2011 — Charles Schwab Corporation announced the acquisition of optionsXpress Holdings Inc in a $1 billion transaction.
- June 10, 2013 U.S. SEC fines optionsXpress, individuals $4.8 mln for naked short sales.
- November 2014 Barry Metzger becomes CEO (previously served as COO)
- October 9, 2017 optionsXpress migrates all client accounts to Charles Schwab & Company
-  FINRA. Retrieved 2010-12-10.
-  moneycentral.hoovers.com. Retrieved 2010-12-10.
- "optionsXpress buys XpressTrade". Reuters. January 24, 2007.
- "Charles Schwab buys OptionsXpress for $1B". Associated Press. Washington Post. March 21, 2011.
- "U.S. SEC fines optionsXpress, individuals $4.8 mln for naked short sales". Reuters. June 10, 2013.