For the past four years, Sukhinder Singh Cassidy was heads down, running Joyus, her women’s e-commerce startup. She was just trying to get through everyday, motivate her team, and create something meaningful and worthwhile. And that was exceptionally hard.
During that time — especially throughout the past year — the conversation about the lack of women in technology has been brought to the forefront. Singh Cassidy knew that she was ignoring it, that she was instead focusing on her children, the company she was running, and the public boards she was advising.
But in January, she finally lifted up her head and thought to herself, “What do I really want contribute to?” If she only focused on Joyus, she was doing a discredit to herself, because she was capable of much more. She has always been an empowered person — if she wants to do something, she’ll do it — but she was missing something. A bigger mission.
“If you care deeply about something, speak up and say something. It’s more effort, but some good will come from it,” she said.
With that in mind, she penned a letter for Re/code called “Tech Women Choose Possibility,” outlining her own experiences and attempting to change the narrative of women in tech. Instead of focusing on the negative statistics and lack of female voices — which paints the picture that women aren’t succeeding — Singh Cassidy showed how they were by surveying 100 women entrepreneurs and highlighting the positive trends.
She called on women to speak their minds and #choosepossibility, instead of being defined by gender bias, and she called on everyone to improve the startup ecosystem. She also started to build a comprehensive list of female tech founders. Singh Cassidy had no idea how it would be received. She was nervous, but publishing the letter and quickly seeing how many people resonated with it was empowering.
“I wrote Sheryl [Sandberg] a note, maybe the day before or after Recode [that said] I always considered myself leaned in, but you’re an example of when you think you’re leaned in enough, there’s always an opportunity to lean in further,” she said.
Singh Cassidy was born in Africa, but her parents immigrated to Canada when she was very young. She grew up in a small town where her father ran a medical practice. From the time she was seven years old, he had her helping out in his office. By the time she was 10, she was able to file his income taxes. Her father was highly entrepreneurial, and instilled that passion in her very early on. He also loved stocks — in the 1970s and 80s, she remembers he would read the paper every day with a magnifying glass because his eyesight wasn’t great. He was one of the first buyers of AOL stock.
That was her first encounter with technology, and she was fascinated by it. Singh Cassidy went to college at Ivey Business School at Western University in Canada and, after she graduated, she moved to New York City to work for Merrill Lynch as a financial analyst. Then she moved to London, and worked for British Sky Broadcasting.
While she was there, she had an itch to start her own company, but had no idea how. She even had a group of women who would brainstorm business ideas. A roommate decided to go to Stanford’s business school, and Singh Cassidy went to visit her. She fell in love with the Bay Area. So, she quit her job to move back to North America, and decided to try out Silicon Valley.
“I slept on a friend’s parents’ couch for almost three months looking for my first job, and my father was the person who encouraged all of that risk taking,” she said.
But her first job almost sent her packing. She was told she was too aggressive, and that she was scaring the secretaries. She was given increasingly menial tasks, and was overall undervalued as an employee. She quit within six months, and then joined the team at Junglee, which was acquired by Amazon soon after.
She had made her mark in business development at Junglee, and felt it was time to start her own company. So, she co-founded Yodlee, a financial data software system. She took the company through four rounds of funding and worked in almost every department. She was topping out.
Then she met Larry Page and Omid Kordestani, who eventually convinced her to take a job at Google, which only had 1,200 employees at the time. She ran the Maps department, and later became president of Asia Pacific and Latin America Operations. She left after six years, when she was pregnant with her third child. It was clear she was topping out there, as well — she was one level below Eric Schmidt, and her peers were Sheryl Sandberg and Tim Armstrong. She wanted to take another shot at running something of her own. So she went to Accel Partners as a CEO-In-Residence while she figured out the next steps.
“I was very passionate about idea of building and running a company serving women, and I declared that’s what I wanted to do next,” she said. “Think about 08-09 — Pinterest hasn’t emerged, Gilt was hitting it out of the park, Polyvore was emerging as a very cool tool, Rent the Runway [emerged]. Inspiration-oriented and discovery-oriented commerce was making a debut… it was clear to me e-commerce was undergoing a revolution.”
And personally, she was very passionate about those types of things — fashion, decor, and design — and at that point in her career, given the choice to start any type of company, she wanted to do something that served the female consumer, something that made women feel good.
After a short stint as CEO of Polyvore, which didn’t work out because she and the founder had differing ideals, she started Joyus in 2011. Joyus is a video shopping company that uses the expertise of professional shoppers, stylists, makeup artists, and nutritionists to help women find what they need and what is best for them.
In the process, she’s created a company with a work culture that she’s always admired and wanted for herself — a canderous, direct environment, with passionate, opinionated people.
“I look around at Joyus, and people are always hungry, they always believe they can be better, maybe almost too much so,” she said. “But they’re pretty confident — you don’t see a lot of entitled people…they’re always trying to achieve more. No matter where you are in your career, I always feel like you should improve.”
Her own resilience has dramatically increased, she added. At a startup, there’s no wind at her back like there was at companies like Google. She can’t parallel processes, and the product doesn’t sell itself like it did there. She did a lot of things right in her career, but she has more grit and hustle now than she ever has.
Now, after her campaign to “choose possibility,” people are asking Singh Cassidy if she’s going to do something more. She hasn’t said what’s next, but she is proud that she has made a contribution to the women in tech movement, and helped shift the narrative somewhat.
“People hungry for solutions. There’s a lot of ideation going on right now,” she said. “That’s good. The valley thrives on ideation. That’s step one — we will see what comes next.”
In her own words….
How do you unplug?
“First of all, between work and kids, there is not much in terms of time. For me, unplugged looks like…tennis, has become my new go-to sport, squeeze out all my aggression, and certainly I love to ski. A big part of it is just down time with my family. You’ll find our weekends are remarkably unscheduled. My children do not do any organized sports on weekends, we are not the family that has them in soccer and baseball — the weekends, no, that’s the only chance I get to spend with them and them with me and so we are incredibly last-minute. That is probably my biggest unplug.
“Late-night online shopping, always. I am the person you are going to find at 11 pm at night. [When I] finish email, there’s no way I could go to sleep if I don’t unwind for another hour, and unfortunately there’s usually a credit card involved in that. But I’m a hunter, anybody will tell you that. If I’m in New York, I will find an hour to go shop. I just love the thrill of the hunt. I am that person. If I have an hour to myself, the number one thing I want to do is go search for something unique. I’m a treasure hunter.”
Looking back, what advice would you give yourself?
“I think I’d give myself two pieces of advice, and maybe they’re counterintuitive or maybe they’re complementary. One is don’t worry, it all works out. I had so much anxiety in my 20s, I was successful everywhere I went, and I was at four different places inside of my 20s, before I settled down into Yodlee and it was always ‘What should I be doing next?’ They were all amazing companies. I could have stayed at any one legitimately and maybe ended up at the same place, and I moved around a lot in my 20s….You just want to tell yourself it all works out like it’s meant to, it really does. And I don’t regret my career at all — I would never have ended up at Google if i would have stayed at Sky. I was very impatient, and I still am, but even more so in my 20s. Essentially, just chill out. It will work out eventually.
The second piece of advice, which I certainly believe now…where there’s smoke there’s fire. When somebody tells you something is a minor problem, it’s on its way to being a major problem, specifically when you’re a CEO. By the time you learn the hire you didn’t work out and wait to fire, it’s probably too late. If you don’t think somebody is a culture fit in the interview process, they probably are not. If you ignore that, you’re probably going to pay for that when you hire them. Where there’s smoke, there’s fire.”