What makes CIOs trust an AI agent? Thira bets it’s not the model.

Sunny Gupta built Apptio to show CIOs exactly where their tech dollars went. It worked well enough that Vista Equity Partners bought it, then IBM scooped it up for $4.6 billion in 2023. But somewhere in that decade and a half, Gupta kept hearing the same complaint from customers: thanks for the dashboard, now can someone actually fix the problem it's pointing at?

That gripe is the entire premise behind Thira, the company Gupta launched with fellow Apptio co-founder Kurt Shintaffer. Where Apptio mapped enterprise spend, Thira wants to act on it, starting with the tangle of IT processes that eat up hours of human time. Ten enterprises are already kicking the tires as unpaid design partners ahead of a fall launch, and Madrona just led a $21 million seed round to get it there.

Gupta isn't promising to automate everything at once. His team mapped six or seven repetitive IT workflows and picked two to nail first, including one that reportedly touches more than 40 separate systems today, work currently handled by people or cobbled-together scripts. Thira's agents ingest whatever documentation exists, including slide decks and hand-drawn diagrams, and build what Gupta calls execution maps of how a given environment actually works. Humans sign off on those maps, deciding which steps are predictable enough to hand fully to the machine and which still need a person's judgment call.

Trust, unsurprisingly, is the whole pitch. Gupta talks about kill switches, audit trails, and rollbacks the way other founders talk about model benchmarks, because a hallucination in an IT system isn't a quirky chatbot moment, it's an outage. Customers start in a semi-autonomous mode where a human still approves actions and everything gets logged, and Gupta figures it takes about a month before most are comfortable flipping to full autonomy.

He's careful to frame Thira as a complement to giants like ServiceNow and Workday rather than a challenger, plugging into the orchestration layer ServiceNow CEO Bill McDermott has been building out rather than competing with it directly. Whether that coexistence holds up once ServiceNow's own agent ambitions expand is the open question nobody in this space seems eager to answer yet. Gupta's real bet is on a flywheel: the same one that made Apptio smarter with scale, where the system supposedly gets sharper once it's run across enough customers, somewhere in the range of 40 to 50 by his estimate. The company itself is tiny for now, just over ten people, mostly engineers pulled from Atlassian, Meta, Databricks, and Oracle, with salespeople coming later once there's something concrete to sell.