What Does IT Look Like When It Actually Works?

For most employees, IT is invisible until something breaks. But for Cal Krome, Head of IT at Calm, that invisibility is the goal. Cal believes IT automation for remote workforce scaling is the foundation of effective modern IT leadership, and in Episode 015 of Go Beyond the Connection, he explains exactly how to build it.

Cal has spent more than two decades in corporate IT, including a defining stretch at Lyft where he was the sole IT person supporting a workforce that grew from 250 to 450 employees. He built more than 40 offices worldwide during that period. Those experiences shaped his conviction that the best time to automate is before you need it.

At Calm, Cal leads infrastructure strategy, cybersecurity, and scalable systems for a fully remote team. The company is 100 percent cloud-based, and Cal’s approach to IT reflects that reality. Access should be fast, secure, and transparent. Systems should support people without requiring them to think about IT at all.

Trust Is the Infrastructure That Holds Everything Else Together

Cal’s first principle is trust, and he applies it in two directions. IT must trust employees to use the tools they request responsibly, and employees must trust IT to have their best interests in mind when systems are updated, access is restricted, or passwords need to change.

That trust is not passive. It is backed by monitoring. Cal describes a model where access is granted quickly based on employee requests, but tools that go unused for 60 days are quietly reclaimed. When leadership sees the results consistently, they extend latitude. When they do not, budget conversations become battles.

“You trust, but verify. You put in place monitoring and safeguards to make sure that if they say they’re using a tool and they haven’t logged in in 60 days — well, take it away.” — Cal Krome, Head of IT, Calm

Automate Early and Build for the Scale You Do Not Have Yet

The most dangerous time for an IT team is when growth is fast and automation has not caught up. Cal’s framework is straightforward: identify the repeating work, prioritize the highest-volume tasks, and eliminate them one by one. When 20 of 300 monthly tickets share the same root cause, that is not a support problem. That is an automation opportunity.

He applies the same logic to security policies. Setting device management requirements and access controls at 50 employees is far easier than retrofitting them at 500. Policies that are in place when someone joins a company feel like standard operating procedure. Policies introduced after the fact feel like something being taken away, which erodes the trust IT has spent time building.

Episode Highlights

• Cal built more than 40 offices globally as the sole IT resource at Lyft during a period of hypergrowth
• Single sign-on through Okta allows Calm to enforce one security standard across every tool in the stack
• Device trust policies ensure that only managed hardware can access company systems, blocking compromised personal computers
• Cal’s team uses AI to generate scripts and answer internal policy questions, freeing engineers to focus on higher-level work
• His closing message: include your IT leader in company planning now, before the goals become fire drills

Listen to the full conversation with Cal Krome on Go Beyond the Connection. Subscribe on your preferred podcast platform to stay current with every new episode from Bigleaf Networks.

The Bigleaf Connection

Everything Cal describes — seamless access, resilient cloud infrastructure, reliable connectivity for remote teams — depends on a network that holds up under real conditions. Bigleaf Networks provides the cloud access network that makes consistent, prioritized connectivity possible for distributed organizations. Learn more at https://www.bigleaf.net/contact.