Leadership
Executive Leadership
Sam Gilliland
Chief Executive Officer
Sam Gilliland
Sam Gilliland is CEO of Cherwell Software, setting the company’s strategic direction and driving its customer-first vision. Sam leads the company’s continued growth beyond IT Service Management (ITSM) and into new markets across the enterprise. Sam draws on his knowledge of and passion for technology to improve customer service experiences and make peoples’ lives easier. For nearly a decade, Sam led more than 10,000 employees in 60 countries as chairman and CEO of travel industry technology giant Sabre Corporation and Travelocity.com. Sam has served on the boards of Sabre Corporation and Travelocity.com, Brinks Home Security Holdings, Carlson, Inc., Gogo, Inc., Rackspace Hosting, Inc., Digital River, and BookingPal. Under U.S. President Barack Obama, Sam 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. Sam 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.
Alison Alfers
General Counsel
Alison Alfers
Alison Alfers is Cherwell’s General Counsel. Before joining Cherwell, Alison was the Chief Legal Officer at HawkEye 360. HawkEye 360 operates a constellation of small satellites used to provide analytic products and services on the use of radio frequency spectrum. Alison also held positions as the Chief Legal Officer at TwentyEighty, Inc. She also served as senior vice president and General Counsel for DigitalGlobe, Inc. where she also held the position of vice president, Defense and Intelligence. Before DigitalGlobe, she served as General Counsel for Knowledge Learning Corporation and SpaceImaging Inc. Alison holds a bachelor’s degree from Arizona State and a law degree from University of Arizona.
Jim Cumella
Chief Revenue Officer
Jim Cumella
Jim is a seasoned sales leadership professional. He is the chief revenue officer of Cherwell Software. Jim was previously vice president of North American Sales for Cherwell and prior to joining our team, Jim led Sales teams for Cyberbit and Imperva, both providers of cybersecurity technologies. In addition, he led worldwide sales teams at Lumigent Technologies and Bunchball before they were eventually acquired. Jim holds a B.S. degree in Business from Fordham University, with a dual major in information systems and marketing.
Scott Gainey
Chief Marketing Officer
Scott Gainey
Scott Gainey serves as Cherwell's Chief Marketing Officer (CMO), driving all marketing activities aimed at increasing the company's brand within the enterprise service management marketwhile accelerating pipeline and revenue growth through close collaboration with sales. Scott came to Cherwell with over 22 years of experience gained while serving in CMO and other leadership positions for some of the most innovative and disruptive technology companies including Palo Alto Networks, Cisco, NetApp, Veritas Software, and Sun Microsystems.
Gary Golden
Chief Financial Officer
Gary Golden
Gary Golden is Cherwell’s Chief Financial Officer. Prior to joining Cherwell, Gary was CFO of Bottle Rocket, a leader in mobile app development and digital transformation consulting. Gary also held CFO positions for Westec Intelligent Surveillance and for Sabre’s European region. He has a broad background, having held senior leadership positions in corporate development, administration, business operations, and law. Gary has an undergraduate degree in business and a graduate degree in law, both from The University of Texas at Austin. He also has a corporate finance certification from SMU.
Board Members
Vance Brown
Board Member and Co-Founder
Vance Brown
Chairman and Co-Founder of Cherwell and CEO of the National Cybersecurity Center, Vance has over 20 years of experience in technology as a CEO and entrepreneur. Currently, Vance is the CEO of the National Cybersecurity Center and mentor to technology entrepreneurs, utilizing the Thrivers.com holistic framework. As co-founder of Cherwell Software, Vance served as CEO from its inception until 2016. Previously, he was CEO of GoldMine Software, now part of Ivanti. Vance co-founded The Classical Academy, the largest K-12th charter school in Colorado, and technology accelerator called Exponential Impact. Vance has been recognized for his business successes and philanthropic work. He currently serves on the board for charitable organizations such as Parents Challenge, Foundation of the Heart, and the Legacy Institute. He also is an Honorary Commander for the US Air Force Academy.
Arlen Feldman
Board Member, Architectural Advisor, and Co-Founder
Arlen Feldman
Cherwell Board Member, Architectural Advisor, and Co-Founder, Arlen Feldman is a renowned software developer in the help desk, service desk, and customer relationship management (CRM) software industry. With more than 30 years of experience, Arlen spearheaded many revolutionary software advances, most notably Codeless Business Application Technology (CBAT) and Platform-as-a-Service (PaaS) in Cherwell Service Management. Arlen served on the Microsoft® C# Customer Council—a small group of industry experts who advise Microsoft on the direction of .NET, Visual Studio, and the C# programming language. He also authored two books—ADO.NET Programming and WPF in Action with Visual Studio 2008. Prior to Cherwell, Arlen was the chief architect at FrontRange®.
Sam Gilliland
Chief Executive Officer and Board Member
Sam Gilliland
Sam Gilliland is CEO of Cherwell Software, setting the company’s strategic direction and driving its customer-first vision. Sam leads the company’s continued growth beyond IT Service Management (ITSM) and into new markets across the enterprise. Sam draws on his knowledge of and passion for technology to improve customer service experiences and make peoples’ lives easier. For nearly a decade, Sam led more than 10,000 employees in 60 countries as chairman and CEO of travel industry technology giant Sabre Corporation and Travelocity.com. Sam has served on the boards of Sabre Corporation and Travelocity.com, Brinks Home Security Holdings, Carlson, Inc., Gogo, Inc., Rackspace Hosting, Inc., Digital River, and BookingPal. Under U.S. President Barack Obama, Sam 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. Sam 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.
Timothy Pfeifer
Board Member and Co-Founder
Timothy Pfeifer
As a Cherwell Software co-founder, Timothy Pfeifer brings exceptional leadership to the team. At Cherwell, he has overall responsibility for the legal, HR and business development areas. Prior to Cherwell Software, Timothy served as the lead attorney for NetSpend Corporation, a TSYS Company, a senior managing attorney for First Data Corporation, and as vice president and general counsel for FrontRange® (formerly Bendata, Inc. and GoldMine Software Corporation). Timothy earned a J.D. degree from the University of Washington, School of Law, graduating as a member of the Order of the Coif; a management degree from Pepperdine University, graduating magna cum laude; and has attended an executive education program through Stanford University's Graduate School of Business.
Rob Salvagno
Board Member, Co-Head of KKR’s technology growth equity business in the Americas
Rob Salvagno
Rob Salvagno (San Francisco) is the co-head of KKR’s technology growth equity business in the Americas. Prior to joining KKR, Mr. Salvagno served as Vice President of Corporate Development and Cisco Investments and was responsible for leading all M&A and venture capital investments for the company. Over his two decades at Cisco, Mr. Salvagno led a significant expansion of Cisco’s corporate venture efforts, including the formation and launch of Decibel – a multi-hundred-million-dollar early stage venture fund – and drove the strategy and execution for some of Cisco’s most impactful acquisitions. Prior to joining Cisco, Mr. Salvagno held technology investment banking roles at Donaldon, Lufkin & Jenrette and PaineWebber. He holds a B.A. in Economics from Stanford University.
John Spiliotis
Independent Board Member
John Spiliotis
John Spiliotis is a go-to-market expert with extensive experience in sales leadership, partner and channel strategy, and enterprise technology operations. He was most recently responsible for driving all Palo Alto Networks direct and indirect sales engagement activities in the Americas as a Sr. Vice President. At Palo Alto, he grew a book of revenue to more than $1.8 billion. He has also held sales leadership positions at Cisco Systems, Avaya, and Ericsson. Mr. Spiliotis holds a master’s degree in finance and banking from Hofstra University and is also a graduate of The Citadel. Mr. Spiliotis is also a Senior Operating Advisor at LLR Partners, a private equity firm, and an advisor at other high-tech growth companies.
Dave Welsh
Partner and Head of TMT Growth Equity at KKR; Cherwell board role: Chairman of the Board
Dave Welsh
Dave Welsh (Menlo Park) is a Member and is Head of TMT Growth Equity within KKR's Private Equity platform, where he serves on the TMT growth equity investment committee. Prior to joining KKR, Mr. Welsh was a Partner with Adams Street Partners, where he focused on technology growth equity investments. Earlier in his career, he was an executive vice president of corporate development and strategy at McAfee, Inc., a general partner at Partech Ventures and a vice president of corporate development at Portal Software. He currently serves on the Board of Directors of Five9, ForgeRock and is a Board Member of SEO Scholars SF as well as being Chair of the Board of Trustees of the Athenian School. He holds a B.A., cum laude, from UCLA and a JD, order of the coif, from UC Berkeley and Harvard Law Schools.
Drew Harman
Board Member. Managing Director, Insight Partners
Drew Harman
Drew is a Managing Director with Insight Partners. He serves as a board member and strategic advisor to Insight’s enterprise SaaS portfolio companies. Prior to joining Insight, Drew was a Board Partner at Shasta Ventures and InterWest Partners, where he sat on the boards of Aria, NewsCred, CloudPassage and GoCheck. Drew has more than thirty years of enterprise software experience as a strategy, product, and marketing executive in early and growth-stage companies, including positions at Ariba as vice president of Product Management, and vice president of Corporate Strategy. Drew also serves on the board of the non-profit Foundation for Prader-Willi Research. He received his MBA from INSEAD, and his BA from Harvard.