Rajeev “Raj” Singh has made a profession out of seeing the following wave earlier than it hits. He guess on software-as-a-service with journey expense large Concur three a long time in the past. He guess on digital care with Accolade earlier than telehealth went mainstream.
Now, he’s betting that Smartsheet can redefine enterprise software program for the AI period.
“If this transformation second weren’t taking place, I in all probability wouldn’t be right here,” Singh mentioned in an interview with GeekWire after his keynote at Smartsheet Interact on the Seattle Conference Middle.
Singh took the stage Wednesday morning on the firm’s annual convention — lower than 30 days into his new function as CEO of the Bellevue-based software program maker finest recognized for serving to companies set up and monitor work.
Based 20 years in the past, Smartsheet is one among area’s iconic tech corporations, with a big buyer base of main companies and greater than $1 billion in annual income. It went personal earlier this yr in a $8.4 billion cope with Vista Fairness Companions and Blackstone.
Smartsheet competes in a crowded and fast-evolving marketplace for productiveness and work-management software program that features legacy gamers akin to Microsoft, Google, and Salesforce, together with newer challengers together with Asana, Monday.com, Airtable, and ClickUp.
Singh, who succeeds longtime CEO Mark Mader, framed the transition as a chance to problem previous perceptions of Smartsheet. He referenced enterprise patrons who nonetheless ask if it’s simply an “on-line spreadsheet firm” or a to-do checklist supervisor.
“It’s time to step out of the shadows for Smartsheet,” Singh mentioned in his keynote speech on the convention, which runs Nov. 5-7 and attracts round 5,000 attendees.

Smartsheet on Wednesday introduced new options as a part of its “Clever Work Administration” platform that mixes AI brokers, data graphs, and automation. The replace introduces instruments like Sensible Help, Sensible Flows, and Sensible Brokers to assist groups create initiatives, handle duties, and spot potential points routinely. It additionally provides new enterprise options akin to Situation Planning and Safety Rating to present corporations extra management and visibility throughout their operations.
Singh described the evolution of AI in three phases: copilots as era one, autonomous brokers as era two, and cross-system automation — the mixing of a number of enterprise tech stacks — as era three.
“That final one is actually laborious, and there’s only some corporations on this planet that may do it,” Singh mentioned. “We’re going to be a type of that lead the world there.”
He mentioned Smartsheet is targeted on utilizing AI to drive enterprise outcomes.
“Brokers aren’t definitionally precious,” Singh mentioned. “What’s precious is productiveness. What’s precious is income. What’s precious is value discount. What’s precious is high quality enchancment. That’s what you’ll be able to cost for — AI is a software, not a income mannequin.”
Underneath new personal fairness possession, Singh mentioned Smartsheet has extra freedom to speed up.
“It offers us extra license to do what we have to do and to go quick — which we’ve got to do,” he mentioned.
Requested how Smartsheet will compete in opposition to AI-driven startups tackling work productiveness, Singh — who not too long ago invested in a Seattle-area AI firm — mentioned incumbents nonetheless maintain the sting “if they’ve braveness.”
“The incumbency benefit is clients, workflows, information,” he advised GeekWire. “If I’ve petabytes of knowledge and also you’ve bought none — for those who beat me by understanding my buyer higher than me, then I used to be asleep on the swap and I used to be imagined to lose.
“You may go quicker constructing software program, however I ought to go quicker constructing perception. And if I lose, it’s as a result of I used to be lazy. If I lose, it’s as a result of I wasn’t paying consideration. And I’d wish to assume that’s not going to be us.”

