When people think of leaving big companies for startups, one of the biggest considerations they assess is financial risk. You’re likely going to take a pay cut, forgo some unvested stock at the current company, and take a leap of faith in the startup’s ability to succeed. That’s important, but in my experience what’s equally if not more important is the experience you’re going to get at the startup, which might significantly accelerate your career down the road or even change your growth trajectory. I’d like to share my experience illustrating this point.
I always worked at big companies. I was fortunate enough to work with many experienced people and learn a lot about how to manage and secure web scale cloud infrastructure. But over time things got a bit repetitive and boring and I wanted to try out a startup. I joined a 20-person company that was on a mission to transform healthcare as its first formal DevOps Engineer.
Back then, I had some clarity on what the setup looked like and what the company wanted me to do and it seemed super exciting, but I had no idea if the company would actually succeed and if I was making the right decision trading off public company RSUs for private company stock options that may very well end up being worth zero dollars down the line. Given the fact that 99% of startups fail, I wasn’t too hopeful about “the big payday.” I didn’t care too much though, since if things didn’t go well I could always return to big companies or do something else. I was ready for an adventure.
Looking back, I’ve had the wildest ride of my life. Fortunately, the company did find product market fit and grew from 20 employees to 250+ employees, adding 400+ customers and raising $250+ million along the way – creating several opportunities for employees to sell some of their stock options and cash out some of the equity, which is great.
While any financial upside is good, the reason I say “wildest ride” is because of the things I got to do here:
Wear multiple hats and flex more muscles
As the first DevOps Engineer at LeanTaaS, I didn’t expect to be greeted with the same level of standards that I had experienced at big companies, but I was still initially overwhelmed. I ended up spending long work days managing the day-to-day while developing a North Star for how things should be and carving out time to get us there. I also ended up being the resident IT person doing everything from onboarding employees at a crazy rate to managing software to fixing laptops to answering help desk calls. I had never flexed so many muscles as I did in the first nine months of this job.
Design and implement major systems and driving business outcomes
I got to think through our North Star for our infrastructure and map out all the critical projects needed to get us there and lead them to completion. We didn’t have any “architects” on board. We had to apply sound engineering principles based on our experiences, read a lot, brainstorm a ton, and execute the plan ourselves while learning and improvising along the way. It was a lot of learning and doing in a very short amount of time.
Manage people and build a team
As the company raised more money, I was asked to hire more people and build out our Infrastructure team. I had led teams before, but I had no management experience. I didn’t even know what management really meant. As a starting point, my manager pointed me to a bunch of books and blogs, which gave me a great crash course, and then spent a lot of 1:1 time coaching me and help me survive and breathe. To be honest, I sucked quite a bit initially but over time, after a lot of battle testing and reading and mentorship, I am now comfortable leading a great team of engineers who make me super proud. We always have a lot of work to do, but we’re quite happy with where we are today compared to where we were four years ago when I started.
Move quickly and participate in a culture of owning and solving problems
Hindsight is always 20/20, but I don’t think I could have gotten so much experience both on the technical side and the people side in such a short time anywhere else. This experience was magnified by being in excruciatingly challenging situations, trying to deal with conflicting priorities and crazy deadlines and simply needing to forge ahead. I also don’t think I was special or my manager was special in making our work and department leap forward. As a small team, we just raised our hands and said “we need to solve this problem” and solved it and moved on. No rules. No hierarchy. No permissions. Of course, we have a lot more process now and our culture has evolved as we grew bigger, but the core “scrappy repeatable execution” is still there and will likely remain even as we continue our growth journey.
In summary, if you’re thinking about leaving a big company for a startup, I’d encourage you to consider exactly what experience you’re likely to gain there and how it accelerates your overall career journey. It’s perhaps worth talking about this with your potential manager and mapping out the role and mission as far out as possible ahead of time to get a solid idea. It’s also worth watching the culture of the team during the interview process and assessing if they have the right mindset – what do they “error on the side of?” How fast are they moving during the interview process? How thoughtful are the conversations? It’s impossible to predict future financial upside, and statistics show that 99% of startups fail. So in my view, the most important thing that’s in your control is to gain “breakout experience” that can accelerate or change your career trajectory down the road and lead to positive outcomes even if the startup fails.
We’re hiring a lot! If you care about making healthcare better, come join us!
Ajaya Loya is an Engineering Manager at LeanTaaS, where he and his team designed and architected reliable, scalable, and secure HIPAA compliant infrastructure that powers all LeanTaaS healthcare products using cutting edge AWS technologies. Prior to LeanTaaS, Ajaya was a Senior Site Reliability Engineer at Yahoo where he worked on large scale internet services; and before that he managed complex environments at Wells Fargo and several other companies. Ajaya is a certified AWS Solutions Architect Professional, Enthusiastic about serverless systems and expert in cloud infrastructure and security.