Sunny Gupta has led two prior enterprise tech companies with backing from venture capital firm Madrona in the past 20 years. iConclude sold to Opsware. Apptio sold to Vista Equity Partners, then to IBM for $4.6 billion.

Now they’re getting the band back together for the AI era. Madrona’s Matt McIlwain is calling it the biggest opportunity “by far.”

Gupta is launching Thira, a Bellevue, Wash.-based enterprise AI startup, with Apptio co-founder Kurt Shintaffer, and leaders from companies such as Atlassian, Oracle, and Databricks. Thira announced Tuesday that it raised $21 million in seed funding led by Madrona, with participation from FUSE.

The idea: Thira is building AI to handle the behind-the-scenes tasks that keep big companies running, like setting up a new hire’s laptop, resetting a locked account, or approving a software purchase. The pitch is to enable a “back-office that runs itself,” according to the company.

It’s starting with IT support. The company is building software agents that can take an IT ticket, work it across the systems where the actual fixes happen — such as ServiceNow, Jira Service Management, Freshservice, and the identity and device-management tools that connect them — and close it out.

Finance and HR systems are also on the roadmap. Thira’s job listings describe agents built to “autonomously run the back-office work that consumes companies today, across IT, finance, HR, and beyond.”

Thira is entering a crowded market. ServiceNow closed its $2.85 billion acquisition of Moveworks last December to build autonomous IT ticket resolution into its service management platform. Startups including Aisera, Rezolve.ai, and Serval are pursuing similar territory.

Part of Thira’s bet is that Gupta and Shintaffer’s relationships with CIOs, which they built over many years at Apptio, will help to give it a foot in the door. Thira says it’s working with 10 companies as design partners ahead of a broader launch this fall.

In many ways, it’s a step beyond Apptio, which helps CIOs see where their companies spend money on technology. Thira is aiming to go past visibility to the “system of execution,” actually doing the work.

In a post on LinkedIn, Gupta said he began hearing from CIOs during Apptio tenure who wanted not only visibility into spending but also the ability to act on inefficiencies and automate work.

“In early 2026, I asked more than twenty CIO friends a simple question: has enough changed that what they’ve been asking for is finally buildable? The answer was yes, and bigger than I expected,” he wrote.

Thira’s team also includes:

• Mudit Goel, previously SVP of engineering at Atlassian;
• Grant Neuman, who was an AI engineer at Oracle Cloud Infrastructure;
• Tarek Madkour, previously director of product management at Databricks;
• and Shashwat Srivastav, previously founder and CEO at AIVOT.

Gupta has been Smartsheet’s executive chair since August 2025, when longtime CEO Mark Mader retired. He also served as acting CEO until Raj Singh was named CEO in October 2025. Shintaffer was Smartsheet’s CFO from July 2025 to May 2026.

McIlwain, the Madrona managing director, is joining Thira’s board of directors. FUSE founding partner Kellan Carter is a board observer.

In a statement, McIlwain said the founding team pairs Gupta and Shintaffer’s two decades of enterprise credibility at Apptio with what he calls “AI-native innovators.” He added, “This is my third time starting and building a company with Sunny and it is by far the largest opportunity we have pursued together.”