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Hillary Stiff of the Washington, D.C., metropolitan area serves as the Managing Director of Cheval Capital, Inc., a boutique investment bank focused on navigating complex financial events, such as mergers and acquisitions (M&A), for small to medium companies. Since joining Cheval Capital in 1994, Hillary Stiff has completed more than 200 M&As and other transactions for website hosting businesses and Internet Service Providers (ISPs). Prior to launching her career in the mid 1980s, Ms. Stiff earned a Bachelor of Science in Business Economics from American University in Washington, D.C. At Cheval Capital, Hillary Stiff contributes to a team of financial experts that has conducted close to $2 billion in transactions over the years, across a variety of industries. This experience, coupled with Cheval’s focus on customer service and its extensive network of active buyers and sellers, enables the firm to find investment partners and complete transactions faster, more effectively, and with less management distractions. A licensed broker-dealer, Cheval maintains membership with the Financial Industry Regulatory Authority and the Securities Investor Protection Corporation. Over the years, Ms. Stiff has served a number of industry leading companies at Cheval, such as Rackspace Managed Hosting; The Endurance International Group, Inc.; and Nippon Telegraph and Telephone Corporation. For these and other clients, Ms. Stiff also compiles a weekly report of M&A activity and companies for sale in their sectors and distributed the listing to hundreds of active buyers. As an expert in the M&A areas of Web hosting and ISPs, Hillary Stiff is frequently sought to lead panels and workshops at industry conferences and events. In the past, Ms. Stiff has spoken at HostingCon (Hosted Services Industry Conference and Exhibition) and the SWsoft Partner Summit.

Work experience


Managing Director

Cheval Capital, Inc.

Chief Financial Officer

Dispatch Communications



American University