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Why I’m at Bitly: Featuring General Counsel Sai Sriskandarajah

This post is part of a multi-part series where we chat with members of Bitly’s leadership team.

If you searched for Sai Sriskandarajah, General Counsel at Bitly, on Slack, you’d see a gavel next to his name.

There was a brief period of time, however, when he considered a career outside of law.

“My first job out of law school was working for a big law firm in New York on securities litigation. It was enough to make me think that I didn’t ever want to practice law again, so I decided to pursue a graduate degree in interaction design for a couple of years.”

If it weren’t for his grad school classmates, who knew he was a lawyer and sought his advice on legal issues related to the projects they were working on, Sai would probably not be at Bitly today—at least not in his current position.

This was a turning point in Sai’s career. He was so interested in helping his classmates, he reconsidered his decision to quit law. Realizing he enjoyed law when he cared about the projects he was helping people build, he decided to move from New York to the San Francisco Bay Area to work in the startup environment.

Sai’s career in the Bay has been marked by a mix of small, medium-sized, and large companies. He held legal roles at Intel and Twitter before working at the startup Mapbox, where he ran the legal team. His excitement for the fast-moving world of technology and getting to dive deep into the day-to-day work of different teams eventually brought him to Bitly.

That’s where our chat with Sai begins. Ready to get started?

SO SAI, WHY BITLY?

It felt like a really great group of people who were smart and were doing really interesting work. On top of that, they also seemed like extremely nice and kind people that would be a pleasure to work with on a daily basis. It turns out this is all true!

Of course, I was also drawn to the business itself. Something I learned while working at a law firm is that I really enjoy getting deeply involved with one business, rather than advising multiple clients. One of the really fun things about working on a legal team is that, even though legal is often the smallest department within a company, it touches everything. There’s not a team at the company we don’t work with in some capacity. So I get to see a little bit of what everyone is doing, which is really interesting because the teams at Bitly are working on some pretty cool and fascinating stuff.

WHAT’S YOUR DAY-TO-DAY LIKE IN THE OFFICE?

I try to keep a third of my day free of meetings so I can get work done, which isn’t always easy since, like I said, there are a lot of exciting things happening here! I also work closely with different teams, helping to answer questions and solve problems.

Sometimes somebody comes to me with something they think is a huge problem but I’m able to solve it pretty quickly. Other times I get pulled into these big, strategic projects where I’m helping figure out how to approach different important topics.

WHAT’S ONE OF THE BIGGEST LESSONS YOU’VE LEARNED THROUGHOUT YOUR CAREER?

It’s a pretty straightforward one. For me to be effective as a lawyer, I need to care about the thing that I’m supporting.

WHAT ARE YOUR TOP 3 LEADERSHIP PRINCIPLES?

One is to build a team that can work well together while still challenging one another to think differently. I think it’s so important to maintain that healthy balance.

I also think it’s my job to enable my team to do their best work. I’m not a command and control-type leader. I view my role as helping to clear blockers for my team and making sure they have the space they need to be really effective.

And that brings me to the third principle, which is to try to be extremely flexible as a leader. I don’t want to force my team members to adapt to my style. I want to adapt to their style as much as possible.

WHAT KEEPS YOU BUSY OUTSIDE OF WORK?

Mostly my family. I read somewhere recently that before you have kids you have 30 free hours a week. When you have one kid you have three free hours a week. When you two kids you have you have negative free time each week. Well, my wife and I have twins, so we went from having zero to two kids, and very little free time. (As in none.)

When I’m not at work, hanging out with my family, or pretending to sleep, at my best I’m a pretty serious cyclist. I’m also an obsessive record collector and general music lover.

HOW DO YOU APPROACH SOLVING BIG PROBLEMS?

I think much of my approach involves avoiding getting overwhelmed. I’ve found that it’s helpful to break a large problem into constituent parts, because often it’s not what it appears to be. Sometimes, it’s totally different. Step two is tackling those smaller problems one by one.

Also, I mentioned earlier that I work cross-functionally with a lot of other teams. So whenever there’s a big problem I think it’s important to ask myself, “who does this impact?” and then figure out who the stakeholders are that I should collaborate with.

WHAT’S ONE THING YOU CANNOT DO?

I can’t throw a perfect spiral.

WHAT’S YOUR FAVORITE BITLY VALUE?

“This land is our land.” It’s the one I was most excited about when I first saw it and I’ve really seen it play out since joining Bitly. People here are willing to jump in to help on things that are completely unrelated to their day-to-day roles. That inspires me and others to do the same. It’s one of those things that is so embedded in the culture that it happens all the time. I wish the world were more like that.

IN YOUR LINE OF WORK, WHERE DOES THE MAGIC LIE?

It’s so hard to really nail down one answer to this question because it’s often the tiniest things. I guess you could call me a professional problem solver, so in my line of work, the magic is in the moment a problem I’m trying to solve gets fixed.

I often tell people that, as a lawyer, at any given time, I’m either a wizard or a janitor. Sometimes, people come to me with a “mess” they need help cleaning up. Other times, they come with a problem they have no clue how to solve, and when I help solve it their response is often, “That was amazing! How’d you do that?!” The sense of elation that comes out of that… that’s why I do what I do.

THIS OR THAT

Fact or fiction? I like reading fiction, but I prefer truth to lies.
Invisible or invincible? Invincible, mostly because invisible seems kind of shady.
10 minutes of snooze or meditation? Snooze. I’m lucky if I get six hours of sleep a night, so every extra minute of sleep is a luxury.
Dishes or laundry? That’s a tough one. I have a love/hate relationship with both, but I think I’m better at getting those 10 minutes of meditation while doing dishes.

Thanks for reading this week’s Why I’m at Bitly post! If you missed last week’s Q&A with Chief Data Officer Amy Bolles, you can read it here.


Tiffany Fowell @Bitly