The new CEO of Smartsheet is Rajeev “Raj” Singh.
That news elicited a murmur of surprise when it reached the GeekWire newsroom, just as we suspect it might for others familiar with Singh, Smartsheet, and Seattle tech as it’s announced this morning.
Singh, the co-founder of Concur, has spent his career doing the heavy lifting of founding and building major enterprise software companies from early stages to massive exits. He most recently served as CEO of Accolade, leading the health benefits tech company through IPO and acquisition.
We didn’t peg him as next in line to run a 20-year-old enterprise tech company that has already gone public, been acquired by private equity, and is now navigating its next phase of growth against entrenched competitors and an aggressive slate of AI-native startups.
But when we expressed as much to him in an interview about his new role, Singh explained that the decision was driven by a combination of several business and personal factors.
Established business, big AI opportunity
First, he pointed to the company’s “exceptional bones” — an iconic Seattle company with a large customer base of major businesses, more than $1 billion in revenue, and significant headroom for growth in the field of enterprise work management.
A self-described product-focused leader, Singh emphasized this point. “I won’t work at a company that I don’t believe has the capacity to build a great product,” he said, noting the “incredible love and affinity that comes from users.”
As a sentimental bonus, Smartsheet’s HQ is across the street from Concur in Bellevue. The expense management company has been part of SAP since its $8.3 billion acquisition in 2014.
Second, Singh was drawn to what he called an “extraordinary” opportunity to implement AI in a tangible way. He believes incumbent companies with established customers, deep integrated workflows, and incredible data sets have a unique advantage in creating AI solutions.
“The opportunity to get my hands on the wheel of a company that I think can have an incredibly tangible impact on business with AI just seemed like a lot of fun,” Singh said. “I think you know me: I’m looking for work where I can have a great time and enjoy myself.”
Finally, the decision was personal. “I want to work with people that I love,” Singh said, citing his longstanding respect for former Smartsheet CEO Mark Mader and his excitement to partner again with Sunny Gupta, who is the company’s executive chair.
The working relationship between Gupta and Singh includes their time at enterprise tech company Apptio, where Gupta was CEO and Singh was a board member, prior to its acquisition by IBM for $4.6 billion in 2023. Gupta was named to be Smartsheet’s acting CEO when the company announced in August that Mader would be retiring at the end of September.
At Smartsheet they’re going to “flip the script,” Singh said, explaining that he’s “excited about partnering up with Sunny one more time to go after something big.”
They face no shortage of competition. Smartsheet operates in a crowded and rapidly evolving technology landscape. Legacy players such as Microsoft, Google, and Salesforce, along with newer challengers including Asana, Monday.com, Airtable, and , are all competing for the same enterprise work-management business.
Challenges of private equity ownership
Singh takes the helm less than a year after Smartsheet was acquired by private equity firms Vista Equity Partners and Blackstone in an $8.4 billion deal that took the company private. Being a CEO under private equity ownership comes with unique pressures and constraints.
However, Singh said he spent a significant amount of time with the board members from Vista and Blackstone and found an “open and receptive audience” for his own hypothesis about the company’s path forward. He sees the owners as “like-minded people” aligned on the goal of growing the business into one of the most important companies in enterprise software.
Shortly after Mader’s departure, Smartsheet laid off more than 120 employees last week. Smartsheet had grown to more than 3,300 people as of a year ago — tripling its headcount over the previous five years, according to its final quarterly filing as a public company.
When asked about the cutbacks, Singh described them as part of a larger transformation happening across the business world, driven by AI and shifting talent needs.
“There are no businesses that don’t need massive transformation right now,” he said. “Anybody who thinks otherwise is missing the story.” In that context, he added, “smart businesses address that proactively… and do it in a smart and humane way.”
Despite the cuts, he said, Smartsheet is a growing business, and he expects the employee base, customer base, and revenue to continue to grow.
As part of the interview, we had to ask the obvious question: What role will Mike Hilton play?
We were only partly joking. Longtime friends and business partners, Hilton and Singh have been connected for most of their careers. Singh and his brother, Steve Singh, co-founded Concur back in 1993 with Hilton, who later joined Raj Singh at Accolade.
More recently, Singh and Hilton backed a new Seattle-area startup called SCALA.AI.
When asked if Hilton would join him at Smartsheet, Singh laughed.
“Trust me when I tell you, I’ve spent a lot of time talking to Mike about this opportunity and getting his advice on the opportunity,” Singh said. “Whether I can lure him away… I don’t know, but I promise you this, he’ll be a wise counsel and a dear friend through the entire process.”
