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From Smalltimore to Big Tech

From Smalltimore

to Big Tech

Sebastian Kurian


Over the years, many law school students and young lawyers have asked about my journey from firm to in-house attorney at two tech titans. I didn’t have the resume that you’d expect of a lawyer at Amazon or Google: I graduated from a mid-tier law school and worked at mid-sized regional law firms, and I certainly didn’t go to law school thinking about a career in tech. For the longest time, I felt like I didn’t really have a helpful answer; I’d shrug my shoulders and point to luck as the reason for my mid-career successes. However, through opportunities like speaking at PracticePro career conferences, I found myself reflecting on my journey and realized that there were key reasons for my so-called success.


I graduated law school a few months prior to the 2008 recession and had, fortunately, secured a firm job in my hometown of Baltimore, aka Smalltimore, a town where people care most about what local high school you attended. Yet, I saw that my luck was tenuous. One by one, many of my peers began to lose their jobs after October 2008. Meanwhile, I crossed my fingers, kept my head down and hustled, seeking out internal opportunities beyond my commercial practice group like trying an actual jury trial. So, maybe it was a matter of the laws of attrition: there just weren’t as many young commercial real estate lawyers to compete with for job opportunities.


As I reflect more deeply on my professional journey, I recall this quote from the Roman philosopher Seneca: “Luck is what happens when preparation meets opportunity.” In other words, what I formerly attributed to luck was actually a combination of putting myself in a position to take advantage of circumstances that presented themselves. Before I share my story and provide some advice, I want to add an important caveat: there is no one-size-fits-all approach; we all can and should take different roads. This is just one story of unintentional job searches.


Nearly a decade ago, I found myself at a career crossroads. I received a clinical diagnosis of depression, a condition that sadly is quite common among attorneys. Each workday, I struggled as I hopped on the DC metro to go to my law firm office. I felt miserable at a job where I found little joy and satisfaction aside from a very comfortable paycheck, which even then provided little solace. Wasn’t I supposed to be happy? Didn’t I want a job where I could make good money? What other opportunities were there?


I began to question whether I made the right decision to go to law school, wondering if the legal path was right for me. I was ready to do something drastic. I applied to the Air Force for an officer role. My wife, who was also at a career crossroads, was about to embark on a fellowship in Africa, and I considered moving with her to volunteer with anti-poaching organizations. But unexpectedly, before I set out on some wild adventure, a recruiter emailed from a company on the other side of the country. It was Amazon. At the time, Amazon, known for being an online retailer, was still a fledgling company. Apparently, the recruiter found me on LinkedIn and thought my background might fit with the company culture, despite not having the exact credentials they typically desired. I often ask myself━would I have responded to the LinkedIn message from Amazon if I was in a job or city that I loved? I came across this surprise opportunity at a time when I felt like I had nothing to lose. After an initial rejection and then several more months of re-interviewing, I landed an offer. I drove across the country to launch a career transformation. As a growing company, Amazon needed help everywhere. I assumed that I’d do work related to real estate or construction, but there was a growing need for a lawyer to support Amazon’s new renewable energy goals. With little competition in such a new space, I thrived in this role at Amazon and then Google (more on how I got to Google below). I want to share four key lessons that might help aspiring or young lawyers in a similar situation:


  1. Don’t be shy on LinkedIn. My first law firm brought in professional consultants to evangelize to its lawyers the benefits of LinkedIn, which at the time was a relatively new social media site. Recruiters discovered me on LinkedIn for in-house roles at Clark Construction and Amazon because of the strong keywords in my profile. Spend time thinking about the important keywords and phrases in your area of practice and incorporating them into your profile━you’ll need these for the AI bots to identify you! I always encourage young lawyers to model their profiles after mine because it is chock full of content that legitimizes my expertise. Use LinkedIn to promote yourself and stay connected to classmates and colleagues. Share recent publications or findings and add a few relevant hashtags so you’re known for your expertise (#litigation #thoughts and #leadership). Don’t feel shy to like posts of people you want to connect with (e.g., a hiring manager, future colleague, or recruiter). Even if these people are not 1st degree connections, you can follow them. Don’t hesitate to connect with folks whose roles are interesting to you (but always include a note to avoid rejection as a random request).

  2. Build long-lasting relationships with your colleagues. Some people think that the key to opening future job opportunities is to rub elbows with executives and other leaders. In actuality, your peers can be the most likely source for job opportunities, particularly those valuable, unadvertised roles. I always joke that it was my dog that got me my job at Google. That’s right; Simba, my teddy bear/border collie/shih-tzu mix got me my job at Google. How’s that? Amazon has always been a dog-friendly company, and Simba had a best friend, Percy. When Percy’s owner flew back to San Francisco to visit his wife every weekend, I would dog-sit Percy. Six months later, Percy eventually became a Doogler (what we call our four-legged friends at Google). Simba and Percy━err, Percy’s owner and I━continued to stay in touch. A few years later, Percy’s owner reached out to let me know that Google Legal was hiring for essentially my same job at Amazon. Over the years at Amazon, I had built expertise in a legal niche that was attractive to Google. We are told how important networking is for our career and professional growth, but what does networking actually mean? It can take on so many different forms. Genuine low-key relationships with no agenda or intention to leverage for the future can often be the ones that lead to unexpected opportunities.

  3. Live below your means. I grew up in a lower-middle-class, blue-collar family that often experienced financial hardship. My first year as an associate was my first exposure to real money, and I didn’t waste any time spending it. I purchased a brand-new condo and BMW sports car. Then, the 2008 financial crisis hit, and every day I worried about losing my job. How was I to pay for a monthly mortgage and car payment? That experience shaped me into a minimalist. I have lived well below my means for the last decade. So, what does this have to do with my unintentional job search? When Amazon reached out, I was in a very mobile situation; I had no debt and rented an apartment. Thus, I had the financial freedom to take on what could have been a risky move: compensation that would largely depend on how well the company stock performed. If I was still saddled by an underwater mortgage or a hefty car payment, I’m not so sure I would have given up a consistent and solid (albeit unhappy) law firm paycheck to make the move, which ended up turning into a financial windfall well beyond what I would have ever made if I stayed at a law firm. While not everyone can make it work, living below your means and having fewer financial commitments can allow you to more easily pivot and tackle rewarding opportunities.

  4. Become an excellent verbal communicator. Earlier, I mentioned the quote: “Luck is what happens when preparation meets opportunity.” Yes, I experienced a bit of luck with having a lawyer friend at Google or recruiters finding me. However, what happens afterward is entirely in your hands. During high school, I placed nationally in speech and debate tournaments. From a young age, I built strong speaking skills and stage confidence/presence. After the recruiter contacts you, it is up to you to present your thoughts well, particularly during high-stress situations, such as Amazon’s grueling interview process. In-house interviews carry tremendous weight; interviewers want to get a feel of how well you vibe with peers and how you might carry yourself in meetings with executives. Seek out opportunities like Toastmaster’s to build your verbal communication skills and undergo a personal journey to build your confidence━it will show in your networking and interviewing.

Again, every journey is different and there is no guarantee that doing A, B, C and D will lead you to E. But just in case, be kind to your dog and his friends; they might lead you right to your dream job!

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