How to be a DevOps Engineer – From Help Desk to CTO

How to be a DevOps Engineer

From a help desk support representative to a CTO & Co-founder, with over 20 years of experience, Tony has played virtually every role in technology. Originally from Southern California, Tony has worked in LA, Silicon Valley, and the Pacific Northwest where he currently resides. In his last venture, he raised over 4 million dollars in venture capital to help live streamers and content creators earn sustainable revenue. He’s written a book about building and growing technical teams in startups and now spends his time consulting and advising other startups. 


In 1997, I was probably in the same shoes as you are now. Trying to break into an industry that requires experience but the whole thing doesn’t make too much sense right? How can you get experience if nobody is willing to hire you without any experience? 

 Back then, there were no smartphones, no apps, and my Internet speed was about 33.6kbps. If someone called your landline, you got kicked off. To put that in comparison with my connection right now, if I did the math right, my speeds were 30x slower. But this isn’t a story about legacy tech, but the beginnings of your new journey. Believe me when I say that if I could get a job in the tech industry back then without the resources available today, you can certainly land a position in DevOps. Here’s a brief background about me. 

I’ve been tech support at a call center, a PC/Network technician, systems engineer, network engineer, platform engineer, data engineer, DevOps engineer, manager, director, VP of Engineering, and CTO & Co-founder of my own venture-backed startup. Before all of that, I was a city-college dropout delivering pizzas. How did I make that transition? Perseverance. 

I’ve been rejected from opportunities hundreds of times. In the early days, I couldn’t even get a job without literally getting laughed at. I spent months applying to jobs in person, and by crafting personal emails to HR departments. I almost gave up, but right when I thought all hope was lost, I walked into a temp agency, unannounced in shorts and a t-shirt, and a week later, I was off to a gig that would change the trajectory of my career forever. 

Jeff Bezos Career Advice
Jeff Bezos Career Advice

I don’t want to bore you with a story that’s over 20 years long, so to sum it up briefly, here are the guidelines I live by to help me get to that next level. 

  1. Expect and accept rejection. 
  2. Persevere and never give up. 
  3. Find your passion and go all-in. 
  4. The journey is never over. 
  5. Find opportunities and capitalize on them. 

Everything you put out there professionally and personally is a reflection of your personal brand. If you are truly passionate about being a DevOps engineer, or anything really, then it should show in all things you do. 

How was your University time?

I spent about a year in a city-college off and on. Back then, it was much harder to get into tech without a 4-year degree from an accredited university. What would be considered DevOps engineering today, doesn’t require a degree, but skills and a drive to learn. Obviously, a 4-year degree helps land a junior role, but if you are graduating with a degree in CompSci, then software development is probably your career choice and not DevOps engineering. 

Why did you choose a career in this field?

I was initially hoping to own a PC repair shop of my own. My father was an auto mechanic, so I thought I would be a computer “mechanic”. Times were different back then too. It seemed like everyone was buying a computer, trying to check out this “Internet thing”. I figured if everyone had a computer, not everyone would know how to fix their broken PC.

I quickly saw that technology is ever-changing. As it evolves, new tech will be new to everyone. The technology I built my career on definitely helps me today, but the field has changed so much that anybody just starting out has a chance to learn about something new, much faster than I do. For example, you can learn about Kubernetes right now for free, while systems administrators of traditional servers may not have the time to learn about it. It was a chance for me to compete in an industry with people having tenured experience but not relevant experience. 

What was your first job or nuggets from jobs you had that helped you get to where you are today?

People don’t care if you don’t know everything. In fact, acknowledging what you don’t know exemplifies two things. One, you are humble, and two, you know where you need to get up to speed. When I got that call back from the temp agency, I was temping at a hospital for 5 months as a PC/Network Technician. I was hired full time and 4 months after that, I received Employee of the Month. I had never fixed computers professionally before so how did I get that? By being honest with people when I didn’t know something, being personable, and always following up. 

I quickly learned that I don’t like saying “I don’t know” so I made it a personal mission to know as much as I can while still admitting when I don’t know anything about a particular subject. That was my way of going the extra mile. Doing what others would not, all within the scope of my job. 

How did you prepare for the interview?

What are you passionate about? If you have a hobby, I’m sure you know the ins and outs of that hobby. Which brands are good, which are bad, how to do this, or avoid that, etc. This is how you should feel about the role you are applying for. Aside from not having real world experience, why do you want to be in the field? If you have landed an interview, then the people involved in the process know your background based on the talks you’ve had with the recruiter, as well as your resume. Show the same passion for the role as you do for your hobbies and it will leave an impression on the interviewers. Also, the more you interview, the easier it will become. 

Imagine you are a big-wig CEO. What type of person would you want to hire? How would you interview them for those qualities? Ask yourself the hard questions and see if you can answer them in-depth. 

For that interview with the agency, I told the recruiter my story and made promises to not let him down. I wanted him to know that I was representing the agency and would maintain their high standing reputation. I let him know I was laughed at before, and really enjoy computers (upgrading all my friends’ PCs), but without much experience, it was challenging. I kept it honest, maybe played the pity card a bit, but connected with the recruiter on a personal level. 

Can you provide some book recommendations?

To be a DevOps engineer, you can read a bunch of books that might be outdated by the time you finish them. The best way to learn is to be hands-on. Immerse yourself in Github, search for “Learning Kubernetes the Hard Way” and the Kubernetes.io documentation. 

Things are changing very fast in the industry; how do you keep yourself updated. Please list techniques or newsletters, podcasts, events, etc.

I look at sites called The New Stack, subscribe to various Slack channels, and attend industry events.  Attend webinars and subscribe to vendor newsletters. For DevOps engineers, we leverage many open-source technologies so getting involved with the community is a huge plus.  If you see a hot tech, try it for yourself.

Stay on top of your field by applying for opportunities that help get you to your goals. When the Public Cloud came out, I found a job that was looking for someone to move their server to the cloud. I didn’t know how to use “The Cloud”, but I did what I have always done. I kept reading, became certified, and finally found an opportunity that believed in me. It’s not always about the technical skills and experience. Sometimes being a culture fit helps a lot. Plus, with the right type of company, your job will help you stay on top of your game.

Any advice about CVs?

Stop trying to inflate your CV with buzzwords. As someone who has reviewed over 1000 resumes, I can sense almost immediately when there’s more fluff than substance. 

Write it in the first person. 

If you feel your resume is lacking, accomplish goals so you can add to it. Just don’t list a bunch of technical jargon because when I hire, I’m looking for progression. Just think, why should anyone hire you? Because you want it more than the other candidates? What if I told you other candidates have told me the same thing, but they have more experience than you? Exemplify your strengths. 

Have a few different versions of your resume. Try to get a sense of the company’s culture and what type of person they are looking for. A lot of people have the same skills as you do or more and are thinking exactly what you are so make yourself stand out. Remember, there are many ways to tell the same story but always be yourself. 

Advice for someone looking for a job?

I know it can be tough, so sometimes it’s hard not to just settle for anything, even though it may not be your first pick. That’s okay. Every choice has a learning opportunity, even if you are learning what not to do. 

Get your foot in the door, and find out what it’s all about. You may not even like being a DevOps engineer, but you’ll never know until you try. Also, it might take a few jobs to get there so figure out if there is a better job suited for your current experience and background that can be a stepping stone to your next jump, like a corporate IT admin. 

Also, it’s not always about the money. I took a few significant pay cuts in my career in order to invest in myself with experience. As long as you keep at it, it will pay off in the future. 

Why do you think you were selected among other candidates?

Humility, honesty, personality, and ambition. Pre-Covid, it came down to culture fit. I tend to ask myself questions like: 

  • What are the team’s guiding principles?
  • What does the team feel is important? 
  • Do the position’s goals align with what I’m looking for?

When those points are mutually agreed upon during the course of the interviews, I knew I got the job. 

In a Covid world, you can only exude so much personality. I recently landed a new job without ever meeting anyone face-to-face. How? I continued to do what I said I would do and when there was a hint of an opportunity, I tried my best to stand out from the crowd. In this particular case, my love for all things DevOps led me to start writing articles on Medium.com for the last year and a half. During the interview, I showed them my account. I’m sure my posts weren’t the reason why I was hired, but it certainly helped since I got the job. I’m sure my experience played a huge role, but even with all that I have done, there is still someone else who has done more. The journey and lessons never stop for me. The only things that change are the goals. 

also read: Web Developer vs Software Engineer

How to be a DevOps Engineer – From Help Desk to CTO

Leave a Reply

Your email address will not be published.

Scroll to top
Land your Dream Job
Get actional first hand insights from people who share their job search stories.