Heute • 1 Std. 4 Min.

Sri Viswanath was Atlassian's first ever CTO. He joined right after the IPO and led the move from on-prem to cloud as revenue grew from $500 million to $2.5 billion and engineering scaled past 7,000 people. After a stint as a VC, he became a founder for the first time. His company, Sycamore, has raised a $65 million seed round to build an operating system for enterprise AI agents. In this episode, Toby and Sri dig into what changes when software can be built, deployed and rewritten autonomously. Sri explains why software starts decaying the day it ships, and why some Sycamore customers are already on version 50 of their apps. He also covers why agents should earn trust over time instead of getting it on day one, and why he believes the more governance you have, the faster you can go. He also looks back on Atlassian, including the cloud migration call he still calls his worst decision. CTOs will come away with a practical framework for moving agents into production: progressive trust, zero-trust agent identity, verification over code review, and the systems thinking that separates real transformation from automating one workflow at a time. - Atlassian's cloud transformation and why it needed a CTO after 14 years - Why software decays after deployment and how a closed loop reverses that - Progressive trust: why agents are never autonomous on day one - Governance as speed: sandboxes, five-second tokens and guarding probabilistic systems - 7,000 engineers for an issue tracker? What scale really takes - Systems thinking, forward deployed engineers and deciding what to build - The engineering org of 2028 and the human-to-agent ratio