Your Future Depends On Taking Big Risks

Q&A with Reddit’s VP of Engineering Nick Caldwell

It’s a crossroads that nearly every IT professional reaches at some point in their career: stay with the safe, steady, reliable career path before you, or take a leap of faith and veer off the beaten track into something new.


Nick Caldwell photo

In the Fall of 2016, engineering leader Nick Caldwell found himself at this turning point. After a 13-year career with Microsoft, Nick was primed for promotion to a senior executive role. But while rising up the ranks of one of the largest tech companies in the world sounded appealing, there was something else calling him — the craving for a new challenge. So he leapt.

Today Nick is the VP of engineering at Reddit, Inc. where he’s grown the engineering department by nearly 400 percent and continues to drive the company forward with exciting new capabilities. We caught up with Nick earlier this month to learn more about making a major career leap, what top tech companies look for when hiring new talent and where he draws his inspiration.


1. You left a 13-year career with Microsoft (where you were on the fast-track to a senior executive role) to work for Reddit. At what moment did you decide it was time to move on, and why did you take the opportunity at Reddit?


I’d always wanted to work at a startup, but Microsoft kept giving me reasons to stay. Each time I was about to leave, there was some new team to try out, or some new promotion to reach for. Eventually, I was promoted to General Manager and shipped a stellar product called Power BI. After that, I could have continued growing into a senior executive role, but I started to feel like I'd achieved everything I set out to do at Microsoft. I'm not the type of person to get comfortable, so I started looking around.

Reddit was exactly the right role for me, and I chose it for three reasons:

First, the engineering team needed to scale rapidly, which is something I'd done before. When I started at Reddit, we had about 35 engineers, and we now have more than 170. All these folks have spent the past year re-building the technical foundations of Reddit and adding whole new capabilities, such as machine learning and a native video platform.

“True freedom is knowing you can use your knowledge and skills to get new opportunities whenever you want.”

Second, I love the product. I have a 10-year-old Reddit account and a lot of opinions about how to make improvements. One of Reddit's company values is "Evolve," and I've really enjoyed working on projects that make Reddit more welcoming to new users. The Redesign is the hallmark project in this regard but our mobile app is also a game-changer and we've got several great new experiences in the works.

Finally, the people have been amazing. Reddit employees are quirky, fun and smart as you'd imagine. There's a fundamental kindness and appreciation for diversity that binds us together.


2. What advice can you offer tech professionals who want to take a risk or pivot their careers, but are afraid to leave behind a good, "safe" job?


Be honest about what you want. If you are genuinely more motivated by family, work-life balance, great co-workers, financial stability, etc., then there’s nothing wrong with wanting to keep your status quo. But if you want to change, then you must make a trade-off and accept that things could get uncomfortable.

Second, demonstrating that you are capable of stepping into new roles and challenges makes changes less risky in the long run. True freedom is knowing you can use your knowledge and skills to get new opportunities whenever you want.


3. As someone involved in hiring new talent and growing teams, what would you say makes a candidate stand out? What qualities do you look for in a new employee?


We're building a world-class engineering team here at Reddit, so naturally, I start by looking at technical chops, the ability to think independently and an appetite for big challenges. But in the modern workforce that's not enough. You've got to be a great team player too. I look for people who are low-ego, know how to take responsibility, share credit and put the group before themselves.


4. We've all heard the sentiment that growth only happens outside your comfort zone. How have you strived to stay outside what's comfortable throughout your career?


I always keep my ears to the ground for big scary problems to jump into (even if I have no prior experience!) At Microsoft, I once took responsibility for a DevOps group although I'd never run a cloud service before. A year after that, I got to lead a mobile engineering team when I'd only previously worked on desktop experiences. In both cases, I volunteered for the roles because they were important to the company, immensely challenging and huge learning opportunities.

“Opportunities are everywhere, but if you sit back and wait for your managers to tell you what to do, then you're not going to find them.”

I also like to create challenges for myself. Like completing my MBA at Berkeley Haas. Getting an MBA isn't easy, it isn't cheap, and it forces you to re-commit to change every time you walk into class. With an MBA you aren't paying for a network, experiences, or a pathway to a new job, you’re paying for a forcing function to speed up your personal and professional growth.


5. Who/what is your greatest inspiration in the tech world? What about outside the industry?


Bill Gates was my tech hero growing up but, right now, I'm inspired by Elon Musk. I love the absurd ambition backed by results. Also, he seems to be having fun doing it all. If I ever start my own company, I'll certainly look for an opportunity to sell flamethrowers on the side. Outside of tech, I saw a Netflix special on Serena Williams the other day that was absolutely mind-blowing.


6. What is one thing you know now that you wish you'd known when you started your career?


Opportunities are everywhere, but if you sit back and wait for your managers to tell you what to do, then you're not going to find them. Managers don't manage your career — you do. Don't complain if things in the team aren't going well. Always try to be a part of the solution. Leaders take responsibility for what happens next.

Also, don't make fun of Javascript. Trust me on this.


7. If you could play one 90s jam on repeat all afternoon, what would it be?


“It was all a dream; I used to read Word Up! Magazine…”


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Carrie Dagenhard
By Carrie Dagenhard

Carrie specializes in technology storytelling while residing in the "Silicon Hills" of Austin, TX.