Rajeev Singh is an American technology executive and entrepreneur. He is the Chief Executive Officer (CEO) of Smartsheet, a workplace collaboration and work execution platform. Singh is best known as a co-founder of Concur Technologies and for his previous leadership as CEO of the healthcare technology company Accolade, Inc.
Early life and education
Singh attended Western Michigan University, where he earned a Bachelor of Science in Engineering (BSE) in 1991. He credits his time at the university, particularly the mentorship of faculty in the Department of Industrial and Entrepreneurial Engineering Management, as foundational to his career in software and leadership.
Career
Concur Technologies
In 1993, Singh co-founded Concur Technologies alongside his brother, Steve Singh, and Mike Hilton. Originally a travel and expense management software provider, Concur became a pioneer in the Software-as-a-Service (SaaS) industry. Singh served in various leadership capacities, including President and Chief Operating Officer (COO). Under his tenure, the company grew to serve over 25,000 customers and was eventually acquired by SAP in 2014 for $8.3 billion, which at the time was one of the largest acquisitions in the history of cloud software.
Accolade, Inc.
Following the acquisition of Concur, Singh joined Accolade, Inc. in 2015 as CEO and Chairman of the Board. He led the company’s transformation into a major personalized healthcare navigation platform, expanding its reach to over 14 million members. He oversaw Accolade’s initial public offering (IPO) in 2020 and its subsequent acquisition by Transcarent in 2025.
Smartsheet
In October 2025, Singh was appointed CEO and a member of the Board of Directors at Smartsheet, succeeding Sunny Gupta. His appointment followed Smartsheet’s acquisition by private equity firms Vista Equity Partners and Blackstone. Singh’s leadership at Smartsheet is focused on the integration of agentic AI and "Intelligent Work Management" to scale the platform's utility for enterprise clients.
Scala.ai
Singh is a co-founder and the Executive Chair of Scala.ai, an artificial intelligence startup based in Bellevue, Washington. Founded in mid-2025 with former Accolade executive Ardie Sameti, the company focuses on building operational intelligence layers for modern contact centers.
Board memberships and philanthropy
Singh serves on several corporate and non-profit boards, including:
Basalt Health (Board Member)
Seattle Children's Hospital Foundation (Board of Trustees)
University of Washington Foundation
Former board roles at Avalara, Apptio, and Amperity.
He is also involved in international philanthropy; his family established a school in rural India that provides education to hundreds of girls.
