“Get Off the Floor” and Other Career Advice from Microsoft, Looker, Reddit & Twitter

Over the past month, we’ve shared a deep dive into how a CEO spends his time, advice for finding a startup idea, and product development frameworks for the first few years of company building. But we always relish the chance to sit down with someone and take a wider-angle lens to tease out the top takeaways from their careers — the leadership lessons, management insights, and pieces of career advice that made the biggest impact. So we were jazzed when we got an opportunity to interview Nick Caldwell, who's got a resume stacked with leadership roles at some of the most interesting and innovative companies around.

The TL;DR: He started his career with a 15-year stint at Microsoft, where he was on the founding team for the company's Power BI product and eventually became its GM. Next came a pair of startup experiences, leading Reddit's engineering team through hyperscale and steering Looker's product & engineering teams through its $2.6B Google acquisition. That brings us to his current role as VP of Engineering at Twitter, where he leads an org that's 700 engineers strong.

It’s a remarkable rise, but what perhaps most sticks out about his career journey is that Caldwell has found success at companies with vastly different cultures, scales and functions. His journey has crystallized one of Caldwell's biggest lessons: "Part of the joy I’ve had over the course of my career is learning that there are a lot of different ways to ship software and get things done," he says.

In this exclusive interview, Caldwell opens up about the biggest lessons that stick with him from each stop in his career journey thus far. Starting with Microsoft, he makes the case that its operating practices are under-appreciated in Silicon Valley. He also opens up about the moment he realized his biggest success at the company meant it was time to move on.

He dives into his functional expertise, including his vision for how product and engineering can play nice, and his system for architecting a roadmap that he honed at Looker.

Finally, he passes on his favorite pieces of wisdom from a few of his mentors, including Reddit's Alexis Ohanian. Although Caldwell’s bread and butter is engineering leadership, there’s plenty to sink your teeth into for managers all over the org chart.

As always, thanks for reading and sharing!

-The Review editors

Recommended resources: 

A Twitter thread on turning networks into economies.

One founder's lessons on boosting productivity with thoughtful communication.

Tips for designing team rituals, courtesy of Lattice.

An inside look at the first 90 days of building a SaaS startup, from a founder that just emerged from stealth.

What you're getting wrong about burnout.

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