Prologue
My former colleague asked, “What does ‘too good of an opportunity to pass up’ actually mean?”
“Wait…really?” and “Nooooooo….” were two common reactions I received from family, friends, and colleagues when I told them I was leaving DocuSign. I was the main UI engineer on the Incubations team, and the job was perfect for me. Those around me knew I really enjoyed my role and the work I was doing.
My first year at DocuSign was full of success. Our team had just launched the first version of DocuSign Search, a long-awaited capability that customers were dying to have. The company-wide engineering learning community that I co-founded had grown from a group of 3 into a bi-weekly meeting of 20+ active participants. Partner teams were giving great feedback on the initiatives and engagements I led with them. And finally, it didn’t hurt that the stock price had shot up. I loved working with my colleagues, my boss was awesome, and the work itself was great. There was no reason to leave.
So why did I leave?
My Intro to WorkOS
When I received a recruitment email about WorkOS claiming itself to be “like Stripe for enterprise features,” it intrigued me. Knowing that Stripe is a rocket ship payments platform, I decided to dig in a bit more.
After an exploratory chat with the recruiter and another with the CEO, I did some of my own digging on workos.com. “Add Single Sign-On (and more) in minutes instead of months,” was a tagline that resonated with me. This reminded me of a developer product that I worked on at Microsoft (before I joined DocuSign) — turning Skype’s frustrating-to-use analytics platform into a delightful self-serve, cross-company product. We transformed a legacy product that took weeks of headaches and manual intervention to use into a modern platform that was automated, self-serve, and easy to get started on within minutes. Not only did I love building a highly polished product, I also enjoyed the startup-like experience where engineers could define and ship their own ideas.
Although apprehensive to the idea of interviewing, I went ahead and decided to continue. The next step in the WorkOS interview was an hour long chat with some of the engineers on the team. I braced myself for a timed coding challenge, but to my surprise, it was just a casual conversation between myself and two WorkOS engineers. I had just as much of a chance for me to interview the team as they had to interview me. It wasn’t the usual tech screen where you were only allotted five minutes in the end to ask questions. Instead, it was a check on both ends on how my values and the company’s values aligned. Building an exceptional experience for customers, which WorkOS calls Developer Joy, is a core value that I could relate to deeply. “Wow, this is how interviews should be,” I remember thinking after the conversation.
The take-home assignment is what started to win me over. The task was essentially to build a small, straightforward full stack web application in technologies of my choosing. I really enjoyed working on it, and it was a taste of what I would be working on at WorkOS. The project was an opportunity for me to experiment with some technologies I had been meaning to play around with, and at the same time to showcase my strengths without someone peering over my shoulder. I really enjoyed seeing it all come together the way I envisioned it would.
Fast forward a week — after a technical pairing session on the assignment and meeting with more folks on the team, I was made an offer! Now the really hard decision process began.
Big Tech vs. WorkOS
DocuSign is great. It was named one of the top ten tech companies to work for in 2021. WorkOS seemed great. Why even consider WorkOS?
I had been at big companies my entire career, and WorkOS is a startup. Why would I risk my then-good career trajectory at a well-known multi-billion dollar company to join a relatively unknown company? The short answer to those questions is what I look for in life: growth.
Growth will mean different things at different points in people’s lives. Career growth at this point in my life means to learn and apply both engineering and non-engineering experiences. At more established companies, you normally have an army of people to take on those non-engineering challenges, and that’s something I wanted to get more exposure to. Being closer to the customer, shaping company culture, and learning more about business operations are all experiences that I would gain at a startup.
WorkOS is not just any startup. It is a company with a second time founder, Michael Grinich, who left his previous startup Nylas to build a solution to the problems that he experienced there. It’s one that many SaaS companies face today: missing enterprise-ready features to be able to sell to large organizations. Though personally I have not dealt with these challenges, the problems WorkOS are solving make a great deal of sense to me.
Embracing the Unfamiliar
I incessantly went back and forth on the list of my pros and cons. I mulled them over on a spreadsheet, spoke to career mentors, consulted family members, friends, past colleagues, and even some colleagues at DocuSign while I was still there. Every single person who knew me well told me to join WorkOS, but even then I felt extremely conflicted. It was a very scary decision — going from the familiar to the unfamiliar.
My desire to take on new challenges at WorkOS conflicted with the comfort of my role at DocuSign. It reminded me of my first time cliff diving in Hawaii — terrified, yet knowing it would be an exhilarating experience. The internal dispute on whether or not to join WorkOS was like a prolonged version of the heavy hesitation I felt as I paced back and forth along the edge of the cliff, while friends and family cheered me on to jump.
I needed to remind myself that each time I have done something that scares me (within reason) in life, it has led to growth in some form or another. For example, after I finished my first sprint triathlon, I achieved something I thought I would never do. My first official presentation in front an organization of 60 people was nerve wracking but gave me a confidence boost in public speaking. Snowboarding down a steep mountain helped me overcome my intense fear of heights, and now it’s one of my favorite hobbies.
“Just jump!”
Will I Regret It?
While interviewing for WorkOS, I also had evaluated it against other opportunities. I looked into several other startups, and even had a very appealing opportunity to go work for Microsoft again. WorkOS still stood out among other startups. Microsoft was really only the serious contender at the time if I were to leave DocuSign.
Opportunities within Microsoft and DocuSign are plentiful, and hopefully will still be around in the future. The chances to join a succeeding early stage startup that I believed in were few and far in between. When my wife said to me, “I think you’ll regret it if you don’t join WorkOS,” that’s when it really hit me. Given all of the factors, knowing I will regret not choosing a particular path means that it’s an opportunity that I should not pass up.
I signed my offer letter with WorkOS, leaving my comfort zone and embarking on an exciting journey of the startup world.
28 Days Later
It has been about a month since I joined WorkOS, and I could not be happier about the decision I made. It hasn’t been all rainbows and butterflies, and as expected there’s a lot to learn. There is a big paradigm shift from going to big company to a startup. Here’s my list of the expected and the unexpected since I have joined:
The Unexpected
- Work/Life Balance is quite good. I thought the startup life would demand hours of my time and folks would be pinging me on weekends and nights. It’s actually quite the opposite, and one of my colleagues gave me an interesting perspective. When you mostly cater to the US Enterprise Market — you will likely operate in hours on US Enterprise time. Customers aren’t requiring your product to be functioning at 2 AM on a Saturday. There has been one major incident that we resolved within minutes in my first month at WorkOS.
- There are so many tools. In a large company with more specialized responsibilities, you get exposed to fewer tools (especially at Microsoft where almost everything you use is Azure-based). At WorkOS, the number of tools and the purpose of each function was something that took some time getting used to.
- Communication is transparent. Since the company is remote, transparent communication is encouraged. This is good and bad. It’s bad in a sense that I tend to get easily distracted and can get lost in looking back in history at past all hand meetings, product discussions, and chat threads. There’s too much available information to consume, and I have rabbit holed myself a few times. It’s good in the sense that you get context on many different aspects of the company, and it’s easy to know what’s going on.
- Imposter syndrome. A brand new environment, unknown faces, and the buzz all around me feels like my first month at college in a new city again. The last engineer that joined before me was 7 months before my start date. In startup-time that equates to eons. With the other engineers working so smoothly and quickly, being this new makes me feel like I’m not learning or moving swiftly enough.
The Expected
- High engineering bar. I was told there is a high engineering bar, and so far I am impressed with the quality of our engineering team (and overall team), the code, and deployment pipelines. Engineers are smart, direct, thoughtful, and exhibit a low-ego. The same goes for everyone else in the organization. We are a high powered team all across the board.
- WorkOS moves fast. Same-day customer fixes, multiple deployments to production a day, and near-instant responses from teammates are pretty refreshing. Friday deploys are a bit scary, but that just speaks to the quality of the engineering we have.
- Everyone cares. At this stage of the company, everyone has to care. Cameras are on, folks are on time, people listen to each other, and most of all each individual is willing to go the extra mile to help each other. There’s a high amount of trust and self accountability. No one needs to be “managed,” as everyone is able to manage themselves.
- Folks wear many hats. It’s been great to have an opportunity to not only to help solve engineering problems, but also to participate in discussions on many other functions such as: company policy, recruiting, marketing content, and direct customer interactions.
- Being close to customers again is fun. It’s been a while since I have interacted with customers directly, and I had forgotten how satisfying it is to be able to help solve a customer issue. It is also amazing to see customers singing praises about our product.
There is so much to learn and lots to do, and I’m excited take on new challenges and make an impact. It’s amazing to see how quickly the company is growing as well. In the short time I have been here we have hired 10+ folks, and we are still hiring! If this sounds like somewhere you’d like to work, you can learn more about open opportunities listed here.
