Apptio founders reunite to launch AI startup Thira with $21M in funding led by Madrona – GeekWire
Sunny Gupta has led two previous technology companies with the backing of mega-enterprise firm Madrona over the past 20 years. iConclude sold to Opsware. Apptio was sold to Vista Equity Partners, then IBM for $4.6 billion.
Now they’re putting the band together in the AI era. Madrona’s Matt McIlwain calls it the biggest opportunity “to date.”
The Guptas are launching Thira, a Bellevue, Wash.-based AI startup, with Apptio founder Kurt Shintaffer, and leaders from companies like Atlassian, Oracle, and Databricks. Thira announced on Tuesday that it has raised $21 million in seed funding led by Madrona, with participation from FUSE.
The vision: Thira is building AI to handle the back-end tasks that keep large companies running, like setting up a new rental laptop, resetting a locked account, or approving a software purchase. The pitch is to enable an “automated back office,” according to the company.
It starts with IT support. The company is building software agents that can take an IT ticket, apply it to all systems where actual maintenance is being done — such as ServiceNow, Jira Service Management, Freshservice, and ownership and connected device management tools — and close it.
Financial and human resource plans are also on the way. Thira’s job listing describes agents designed to “automate the back office work that consumes companies today, across IT, finance, HR, and beyond.”
Thira enters a crowded market. ServiceNow closed its $2.85 billion acquisition of Moveworks last December to create an independent IT ticketing solution in its service management space. Startups including Aisera, Rezolve.ai, and Serval follow a similar path.
Another thing that Thira observed is that Gupta and Shintaffer’s relationship with CIOs that they have built for many years at Apptio, will help it enter the market. Thira says it is working with 10 companies as design partners ahead of a wider launch this fall.
In many ways, it’s a step ahead of Apptio, which helps CIOs see where their companies are spending on technology. Thira aims to go beyond appearances in the “execution program,” actually doing the work.
In a post on LinkedIn, Gupta said he started hearing from CIOs when he was in charge of Apptio who wanted not only visibility into spending but also the ability to streamline and automate tasks.
“At the beginning of 2026, I asked more than twenty CIO friends a simple question: have you changed enough that what they were asking for can finally be built? The answer was yes, and it’s bigger than I expected,” he wrote.
Thira’s team includes:
Gupta has been Smartsheet’s chairman since August 2025, when CEO Mark Mader retires. 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, managing director of Madrona, joins Thira’s board of directors. FUSE founding partner Kellan Carter is a board observer.
In a statement, McIlwain said the founding team includes Gupta and Shintaffer’s two decades at Apptio and what he calls “native AI innovators.” He added, “This is my third time starting and building a company with Sunny and it’s the biggest opportunity we’ve pursued together.
