I Was Told I Was Average. They Weren’t Wrong—At First.

I didn’t have the perfect resume. I wasn’t a coding prodigy, a rockstar designer, or some Silicon Valley wunderkind. I was just another engineer trying to figure things out. At least, that’s how it started.

I didn’t come from pedigree or privilege. But I learned that success in tech isn’t about following a straight path—it’s about knowing which moves to make and when.

From my early days at Amazon to leading teams at Smartsheet, Kajabi, and now as CPTO at Kickstarter, I didn’t just climb the ladder—I moved sideways, diagonally, and sometimes even backward. But with every move, I built new skills that compounded over time.

Three things made all the difference:

Taking risks – Saying yes before I had all the answers, then figuring it out.
Building relationships – Making sure the right people knew my work, and more importantly, knew they could trust me.
Ramping up quickly – Becoming valuable in any new domain by learning fast and executing even faster.

That’s how I went from an engineer to leading product, technology, and design at scale. And that’s how I earned a reputation as being "calm but oddly ambitious"—steady under pressure, but always pushing forward.

And along the way, I realized:
💡 No one teaches you how to actually do this job.

Most people don’t need another framework. They need survival skills. They need someone to tell them:

How to manage up and get leadership to listen.
How to say no without burning bridges.
How to handle hard conversations—which, by the way, is why I wrote How to Deliver Bad News and Get Away With It (https://www.amazon.com/dp/B0D7FHTTNN)!
How to build a career on your own terms, even if you don’t check every box.

If you're figuring all of this out, I want to help.

I write about tech, leadership, and all the things they don’t teach you in school. → Subscribe to my Substack: The Sensible Manager (https://maheshguruswamy.substack.com/)

I mentor on Intro—grab time with me (https://intro.co/MaheshGuruswamy) and let’s talk about how to actually make this job work for you.

I was never the smartest person in the room. But I learned how to play the game—and win it. If you're trying to do the same, let’s connect.