Spotlight: Ryan Lewon

Ryan Lewon PicRole: Sr. DevOps Engineer


Hire Date: January 2014


Fun Fact: I used to ride BMX professionally.


“There’s a lot of transparency here at Chegg. You don’t have to worry about where the company’s going because Dan, our CEO, always talks about it and is extremely open to everybody in the company. I love that because you know what’s going to happen the next week, month, and even farther along down the road. This is a great representation of our values around transparency and communication.”

What did you do before coming to Chegg?

I used to work for the Pixar division of Disney in Burbank as a Senior Systems Engineer in which I specialized in Chef, a systems integration framework. While I was there, I simplified their Chef system/deployment pipeline by rewriting it to utilize new technology such as Rundeck, which allows for actual developers to deploy to the platform without having to rely on the systems team even being awake while they’re doing this. Instead of going through 15 hoops and my manager telling me to get it done, it turns into submitting a ticket to get done and it’s done. However, once they transferred me over to the ABC Dancing with the Stars and Oscars sector, I decided that it was time to move on.

Why did you decide to come to Chegg?

My wife is going through school right now and I had planned on finishing college for a very long time, and since Chegg is all about education and students, it was a very attractive company for us to look at. I also work remotely from home while I’m able to pursue my degree, so that made the decision to come here even more attractive. Plus, my friend Tim worked here and told me, “Dude this place is awesome! If you could come work with me, it’d be the best place to work for in the world.” And so far, it’s been really awesome!

Has anything surprised you about working here?

The openness of everybody working here has been surprising to me because you don’t have that at a lot of companies, especially from the perspective of being a remote employee. There’s a lot of transparency; you don’t have to worry about where the company’s going because Dan, our CEO, always talks about it and is extremely open to everybody in the company. This is very different from when I was working at Disney, where one week I was working for Pixar, next week I’m not. I love the openness because you know what’s going to happen the next week, month, and even farther along down the road; nobody’s hiding anything from you, especially for as many employees as we have.

How did you get into DevOps?

I started doing customer support for a web hosting company when I was 18 or 19 years old. Doing customer support is the same thing ALL OF THE TIME. Back then, there was no real way to do this repetitive work very easily, so I started teaching myself how to code and would program things on my own time. Once I had learned how to do this, I brought that knowledge into work to write things to help prevent us from doing the same, repetitive work all of the time. Even when they didn’t allow us to implement it, it was still something we could run locally and basically copy and paste it somewhere else, making it ten times easier to actually work with.  And now I’m here! You learn a lot from Google, but you have to have some hidden ability to build upon. I’m fortunate enough to have a lot of people in the Chegg office that have those abilities and actually know where they’re coming from. It’s not like forced upon; we enjoy having fun doing this versus going to school to study this because our parents said so.

What are you proud of?

I’ve been working on a project called Chef Metal with guys from Opscode, who created Chef, and all of the patches I’ve contributed to it so far have helped Chegg as a whole. I automated a lot of the platform procedures that we had in place that weren’t really in existence before. Previously, we had a lot of manual procedures in place, which I’ve now replaced with one short command unlike the other methods, that were not only not just long, but cumbersome too. My focus is taking a lot of the tedious tasks that were repetitive and monotonous and turning them into something like “click” or faster and off they go, whereas in the past, they had to sit there and search through a wiki to find what variable do they need to change here or what do they need to do there. Another thing I’m proud of is bringing Chef to Chegg.

What advice do you have for someone who wants to start in a role like this at Chegg?
The best advice I can give you is to just tinker; tinker with anything you can get your hands on. From an engineering perspective, learning how to do something on your own versus having to ask someone to do it is an amazing trait you can pick up on your own. Being naturally curious and having the ability to take the initiative to learn and play with new technologies is key to getting you into a place like Chegg. Although, it also helps that everyone communicates a lot and we all share the same information, so we all form a good knowledge pool, which is always a nice resource to have as well. It’s also nice that when we have projects to complete, we have guidelines for what the finished product needs to be, but the fun part is figuring out the way you want to get there.

What excites you most about Chegg’s future?

A lot of the things we’re doing, especially on the cause and donation front with our Chegg For Good Initiatives. I also really have enjoyed our #CheggChats series, meeting and listening to leaders from different industries — meeting Adam Braun from Pencils of Promise, our most recent speaker was really inspiring. Also, bringing a lot of new talent into the world is a big thing. For example, we have 25 summer interns coming this year and it’s inspiring to have students who want to intern at Chegg. “Oh I heard about them when I was at school and I got books from them. That would be awesome to work at a company that has a product I already use every day.”

We’re giving students the opportunity to do things they never were able to afford before. Say, they didn’t even get a loan for school that was big enough to pay for all of their books. They go on and bam! They have books that are half the cost. It’s an awesome opportunity for students and there is so much more we are going to be able to do in the future which makes me pumped!




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