Hillary  Stiff

Hillary Stiff

Managing Director of Cheval Capital, Inc.

Currently employed at Cheval Capital, Inc.

Previous: The Cheval Group, Dispatch Communications



    Investment banker Hillary Stiff has built a career based on personal contacts and close communications. As Managing Director of Cheval Capital, Inc., a boutique investment bank, she supports clients in completing acquisitions, sourcing capital, and navigating a variety of complex financial transactions. With a focus on hosting and ISP (Internet service provider) industry acquisitions, she has completed more than 210 transactions for a large number of clients such as Endurance International, NTT/Verio, SingleHop, Web.com, Hostopia, and Jumpline. Hillary Stiff leads clients through the acquisition process with a gentle hand, ensuring that they thoroughly understand each step and receive the maximum financial benefit. In order to provide the best services to her clients, Hillary Stiff closely monitors market and technology trends and maintains long-term relationships with potential buyers and sellers in the industry. She remains continuously apprised of possible purchase and sales opportunities, and she communicates these opportunities to her clients through her weekly Acquisition Opportunities List. The list summarizes hosting and other Internet services businesses available for sale, and typically includes more than 30 potential acquisitions. Hillary Stiff works closely with each client, developing financial strategies and solutions that meet organizational goals. She also works with professionals in the web hosting industry, providing clear explanations of financial topics to those without strong accounting or business backgrounds. A frequently requested speaker at top web hosting conferences nationwide, she was named to WHIR Magazine's Web Hosting All Star Team in 2009. Hillary Stiff holds a Bachelor of Science in Business Economics from American University in Washington, D.C. She served as Chief Financial Officer of Dispatch Communications until the company's acquisition by Nextel in 1993. The following year, she and her husband cofounded Cheval Capital. Together, they continue to encourage the growth of the company.




At Cheval Capital, Inc.

From 1994 to Present


At The Cheval Group

From September 1993 to September 1994


At Dispatch Communications

From 1989 to September 1993