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Pride and Joyus

by Kathryn Kinahan, BA'86, MLIS'93 | October 13, 2017

From St. Catharines to Silicon Valley, the journey wasn’t always easy or straightforward for Sukhinder Singh Cassidy, HBA’92. But throughout her career, the tech world power player has put herself in a position to succeed by both seeing what is next and understanding the diversity of talent needed to help her get there.

Singh Cassidy grew up in St. Catharines, Ont., with two sisters and her parents, both doctors. She chose Western because it offered unlimited opportunity: business, medicine, law. The number of available programs and freedom to choose was a perfect match for someone still deciding on a career path.
At Western and the Ivey Business School, she learned to think broadly and laterally.

“I was able to get my toes wet on really creative problem-solving and consider an issue five different ways,” she remembered. “It opened my eyes to all the opportunity out there. I mean, when I started my HBA, I didn’t know consulting from investment banking from entrepreneurship. The business school gave me the confidence to pursue all those different opportunities and feel like they were actually achievable. That was a big factor for me.”

During her fourth year, when everyone else was in recruiting for jobs, Singh Cassidy went to Belgium on exchange. “When I came back, recruiting season was done. I had a difficult time getting started because most of the jobs I wanted had already come and gone.”

She persevered, staying in London, looking for work and waiting for the next recruiting cycle. When a job still didn’t materialize, she began to get discouraged.

Through a friend, and fellow Ivey graduate, her resume found its way to Merrill Lynch in New York City. She received a notice from the company suggesting an information interview if she was ever in the city. Thinking it a form letter, Singh Cassidy didn’t pay it much heed.

“Then my father said to me, ‘What have you got to lose? Why don’t you book yourself a train ticket to New York and just go meet them?’ So I headed to New York,” she said.

From that initial information interview, she was fast-tracked through the recruiting process and ended up with a job on Wall Street. “Basically, a year after I graduated, I started my dream job. I credit Western for my education, as well as a combination of persistence, timing and luck.”

After a stint in investment banking, Singh Cassidy moved throughout the tech world, including and News Corp’s BSkyB, eventually spending almost six years as Google’s President of Asia-Pacific and Latin American operations. In between, she co-founded Yodlee, a financial-services company and later served as CEO of the fashion site Polyvore.

After Google, she spent time with a venture capital firm studying everything in e-commerce – an area, she believed, was on the brink of reinvention. She was interested in the idea of integrating lifestyle interests within e-commerce. Think merchandise, fashion, beauty, home, interior design.
An added dimension she considered was the emerging power of video.

“Watching the rise of YouTube, it was very clear to me that video and commerce had yet to be married. And you only need to look offline at QVC and HSN (Home Shopping Network), both multi-billion-dollar businesses, to realize there was going to be a shopping channel for the Internet at some point,” she said.

In 2011, Singh Cassidy founded Joyus, an online retailer that operates an e-commerce video platform that allows customers to purchase products directly from the company’s website or video player.

Starting any new company carries a certain degree of risk. “Consumer Internet companies are high risk because people are really trying to create a new category,” said Singh Cassidy, who serves as Chair of Joyus.

There are a lot of factors at play: consumer adoption, timing, serendipity, luck. “But there is also an ‘X’ factor in consumer Internet businesses. Sometimes the first player is the first and biggest. Sometimes it’s not just about the idea – it’s about timing. Is the consumer ready? Is the market ready? I mean, before Facebook, there was Friendster and Myspace,” she said.

Being an entrepreneur was second nature to Singh Cassidy.

“My parents ran their own medical practice for 30 years. My father loved being an entrepreneur as much as he loved being a doctor. He always told me to work for myself and showed me what entrepreneurship looked like,” she said.

When she was in school, she was taken with the notion of being an executive. Although she was content working on Wall Street and with BSkyB in the executive suite, her father’s words kept coming back to her. By her mid-20s, the idea of entrepreneurship was percolating. She visited a friend at Stanford Business School and fell in love with the Bay Area. Her thoughts crystallized.

“While I didn’t have a specific business idea and didn’t really know how to become an entrepreneur, I knew if I moved myself to the Bay Area where all these start-ups were happening, where entrepreneurship was happening, I would have a better chance of figuring it out,” she said.

Two decades later, Singh Cassidy is a powerful voice in the tech world advocating about the importance of diversity among its ranks.

Earlier this year, she spoke out against U.S. President Donald Trump’s executive order on immigration and changes to the H-1B visa program. Herself a beneficiary of the U.S. foreign worker program, she stressed its importance in bringing – and, potentially, keeping – talent in North America.

By 2013, she was tired of hearing complaints with no solutions for the lack of women in the tech industry. “The argument that because ‘we don’t have enough girls in STEM, there’s a problem with women in tech’ didn’t make sense to me. There are numerous examples of successful female leaders at tech companies: Susan Wojcicki, CEO of YouTube; Sheryl Sandberg, COO at Facebook; or myself at Google.”

Given the large number of private companies in Silicon Valley, she recognized their board rooms as a golden opportunity to include more women.

In 2015, Singh Cassidy started theBoardlist, a curated, exclusive peer-to-peer site that helps tech companies find qualified, experienced women for their corporate boards. The company currently has 1,600 women listed, all recommended by their industry peers. In April 2017, she rang the opening bell at the Toronto Stock Exchange to mark the Canadian launch of theBoardlist.

“To me, starting theBoardlist was a way to give back and a way to change the narrative,” she said.

Today, Singh Cassidy lives in the Bay Area with her husband, Simon, MBA’94, and their three children.

This article appeared in the Fall 2017 edition of Alumni Gazette
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