Rajeev “Raj” Singh has made a career out of seeing the next wave before it hits. He bet on software-as-a-service with travel expense giant Concur three decades ago. He bet on virtual care with Accolade before telehealth went mainstream.

Now, he’s betting that Smartsheet can redefine enterprise software for the AI era.

“If this transformation moment weren’t happening, I probably wouldn’t be here,” Singh said in an interview with GeekWire after his keynote at Smartsheet Engage at the Seattle Convention Center.

Singh took the stage Wednesday morning at the company’s annual conference — less than 30 days into his new role as CEO of the Bellevue-based software maker best known for helping businesses organize and track work.

Founded two decades ago, Smartsheet is one of region’s iconic tech companies, with a large customer base of major businesses and more than $1 billion in annual revenue. It went private earlier this year in a $8.4 billion deal with Vista Equity Partners and Blackstone.

Smartsheet competes in a crowded and fast-evolving market for productivity and work-management software that includes legacy players such as Microsoft, Google, and Salesforce, along with newer challengers including Asana, Monday.com, Airtable, and ClickUp.

Singh, who succeeds longtime CEO Mark Mader, framed the transition as an opportunity to challenge old perceptions of Smartsheet. He referenced enterprise buyers who still ask if it’s just an “online spreadsheet company” or a to-do list manager.

“It’s time to step out of the shadows for Smartsheet,” Singh said in his keynote speech at the conference, which runs Nov. 5-7 and attracts around 5,000 attendees.

Smartsheet on Wednesday announced new features as part of its “Intelligent Work Management” platform that combines AI agents, knowledge graphs, and automation. The update introduces tools like Smart Assist, Smart Flows, and Smart Agents to help teams create projects, manage tasks, and spot potential issues automatically. It also adds new enterprise features such as Scenario Planning and Security Score to give companies more control and visibility across their operations.

Singh described the evolution of AI in three phases: copilots as generation one, autonomous agents as generation two, and cross-system automation — the integration of multiple enterprise tech stacks — as generation three.

“That last one is really hard, and there’s only a few companies in the world that can do it,” Singh said. “We’re going to be one of those that lead the world there.”

He said Smartsheet is focused on using AI to drive business outcomes.

“Agents aren’t definitionally valuable,” Singh said. “What’s valuable is productivity. What’s valuable is revenue. What’s valuable is cost reduction. What’s valuable is quality improvement. That’s what you can charge for — AI is a tool, not a revenue model.”

Under new private equity ownership, Singh said Smartsheet has more freedom to accelerate.

“It gives us more license to do what we need to do and to go fast — which we have to do,” he said.

Asked how Smartsheet will compete against AI-driven startups tackling work productivity, Singh — who recently invested in a Seattle-area AI company — said incumbents still hold the edge “if they have courage.”

“The incumbency advantage is customers, workflows, data,” he told GeekWire. “If I have petabytes of data and you’ve got none — if you beat me by understanding my customer better than me, then I was asleep at the switch and I was supposed to lose.

“You might go faster building software, but I should go faster building insight. And if I lose, it’s because I was lazy. If I lose, it’s because I wasn’t paying attention. And I’d like to think that’s not going to be us.”