Meet Carla De Silva, Counsel, Square. A working mom, Carla believes that setting challenging goals for ourselves makes us stronger in the long run. Her #1 piece of career advice? “Never give up on yourself.”

Fairygodboss of the Week: Carla De Silva
Counsel, Square
San Francisco Bay Area

FGB: Tell us a little about your career. How did you get to where you are now?

CDS: I started my legal career a little over 15 years ago, working in the financial sector for several banks, then ultimately moving into the Fintech space.  As a working mom, I gravitated toward in-house work for the flexibility it provided me. I really enjoy the problem solving and collaborative teamwork that my job allows me. At Square, as the lead Product Counsel for Square Capital, I work with an amazing group of lawyers and business partners to build products that help our customers grow.

FGB: What is an accomplishment that you are proud of?

CDS: As I’ve moved to new jobs, I have always been proudest of leaving behind teams, systems, procedures, and structure in place in a better state than when I found them.  

FGB: What is a challenge that you've faced and overcome?

CDS: Looking back, I would say that becoming a single mom in my last year of law school, taking and passing the Bar and then ultimately pursuing a profession dominated by men was a significant challenge that I overcame with a lot of perseverance and dedication to meeting those two goals. Finding the path that allowed me to raise my son and stay fulfilled both personally and professionally left me discouraged at times, but the daily struggles I overcame gave me experience and strength to move from one challenge to the next.

FGB: What is the #1 career tip you'd like to share with other women who want to have successful careers like you?

CDS: Never give up on yourself; we are all stronger than we give ourselves credit. If you set goals that challenge you, they will make you stronger in the long run.

FGB: Who is your Fairygodboss? and Why?

CDS: I’m grateful to have a few Fairygodbosses: my mom, my dad, my sister, my boyfriend and even my son (for a 19-year-old he seems to know a lot); they all listen and support me.  But I do want to call out my current boss, who is an amazing woman and a brilliant attorney, a working mom who somehow manages to balance work and life and helps me remember to do the same!

FGB: What do you do when you're not working?

CDS: I absolutely love to cook and be outdoors whenever possible. Hiking, paddle boarding, camping are all fun, but I’ve always had a passion for cooking since I was a little girl sitting on the stool in my grandmother’s kitchen. She was an amazing cook and a strong role model and she taught me to take risks and be creative in the kitchen. Those lessons went to a deeper philosophy about life in general.

FGB: If you could have dinner with one famous person - dead or alive - who would it be?

CDS: This is a tough one. I’d love to have dinner with Anthony Bourdain. I read one of his books a few years ago and I am fascinated by anyone who can test the limits of their own humanity and come back the way he has. He has such a unique attitude toward food and it’s preparation.  Plus, I’d love to have him in the kitchen to help me make a meal!

Lightning Round

FGB: What is your karaoke song?

CDS: “Crazy Little Thing Called Love” by Queen. I just loved Freddy Mercury. And “Me Siento Guajira” by La Lupe; it reminds me of my roots.

FGB: What is your favorite movie?

CDS: I’m a total sci-fi geek: Fifth Element, because it’s a cult classic and so cheesy it’s good.

FGB: What book would you bring with you on a desert island?

CDS: Jane Austen’s “Pride and Prejudice” would be high on the list as my go-to, but I just started reading “Blink” by Malcolm Gladwell and I’m fascinated by his exploration of the psychology of snap decisions and quick thinking.

FGB: What is your shopping vice? What would you buy if you won the lottery?

CDS: I like shopping for others, especially birthdays, special occasions and holidays. Lotto money would go to purchasing a retirement home somewhere tropical near the water.  


Fairygodboss is all about women helping other women. So each week, we celebrate a woman who makes a difference in other women’s careers. Is there a woman who has made a difference in your career? Celebrate and thank her by nominating her here.