Sam Gilliland Cherwell Software CEO Rating

Cherwell Software CEO Sam Gilliland Bio

Sam Gilliland is CEO of Cherwell Software, setting the company’s strategic direction and driving its customer-first vision. As the global market for service management technology enters the era of digital transformation, Gilliland leads the company’s continued growth beyond IT Service Management (ITSM) and into new markets across the enterprise. He works to ensure Cherwell gives customers the platform and solutions they need to experience smarter service and automated workflows and, ultimately, achieve meaningful and measurable transformation faster.

Gilliland draws on his knowledge of and passion for technology to improve customer service experiences and make peoples’ lives easier. For nearly a decade, Gilliland led more than 10,000 employees in 60 countries as chairman and CEO of travel industry technology giant Sabre Corporation and Travelocity.com, where rapid innovation and personalization were keys to the companies’ successes. Prior to becoming chairman and CEO of Sabre, Gilliland served in several senior leadership positions including executive vice president, chief marketing officer, and group president of Airline Solutions.

Gilliland’s career is marked by a wide range of experience, which underscores his deep understanding of the technology sector – from macro market movements to the code that defines products. Most recently, Gilliland served as senior advisor with investment firm Dimensional Fund Advisors and executive partner with Siris Capital Group, a technology-focused private equity firm. Early in his career, Gilliland worked as an electrical engineer for Lockheed Missiles and Space in Austin, Texas.

In addition to serving on the board of directors for Sabre Corporation and Travelocity.com, Gilliland formerly served on the boards of Brinks Home Security Holdings, Carlson, Inc., Gogo, Inc., Rackspace Hosting, Inc., and Digital River.

Throughout his career, Gilliland has maintained a commitment to civic and community engagement. Under U.S. President Barack Obama, Gilliland served on the President’s Management Advisory Board and on the Energy Security Leadership Council. He also served as chair of the U.S. Commerce Department’s Travel and Tourism Advisory Board.

Gilliland holds an M.B.A. from the University of Texas at Dallas and a bachelor’s degree in electrical engineering from the University of Kansas.

Cherwell Software CEO Sam Gilliland At a Glance

The CEO score provides an understanding of how employees feel about the CEO’s leadership style and effectiveness at Cherwell Software.

Based on 218 ratings, Sam Gilliland ranks right above ServiceNow's CEO, Bill McDermott.

Cherwell Software's CEO is highly regarded by the HR department, the Sales department, and the Marketing department. However, employees who have been at the company 2 to 5 Years, Non-Binary employees, and the Finance department have a less favorable view of the CEO and believe there is room for improvement. Overall, the CEO score has remained stable over the last 90 days.