Technology

My Big Jump: Sukhinder Singh Cassidy’s CEO Journey

Sukhinder Singh Cassidy Contributor

Sukhinder Singh Cassidy founded theBoardlist, a premium talent marketplace that helps diverse leaders get discovered for board and executive opportunities. A technology executive and entrepreneur, board member and investor, she has 25 years of experience founding and helping to scale companies, including Google, Amazon and Yodlee.

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After listening to others pitch me a few different job opportunities while still at Google in 2008, it became clear to me that I would make a better decision if I could fully explore the larger landscape of new companies emerging in Silicon Valley.

I had spent the last several years focusing on Google’s business outside the U.S., and I honestly felt out of touch with the startup world. Beyond my goal of becoming a CEO of my own company, I had two other ambitions: I wanted to help build a great consumer service that would delight people (potentially in e-commerce) and I wanted to build further wealth for myself and my family.

To better evaluate my options, I made the decision to quit Google first and find a way to study the wider ecosystem of companies before choosing where to go. Resolved to give myself a “blank slate” before making a final choice, I left Google when I was three months pregnant and joined Accel Partners, a top Silicon Valley venture capital firm and an investor in my previous startup, in a temporary role as CEO-in-residence.

In the months that followed, I helped Accel evaluate investment opportunities across a wide variety of digital sectors, with a particular focus on e-commerce, taking the opportunity to study those companies I might join or think of starting from scratch.

On Thursday, August 19 at 2 p.m. PDT/5 p.m. EDT/9 p.m. UTC

Managing Editor Danny Crichton will interview Sukhinder Singh Cassidy, author of “Choose Possibility,” on Twitter Spaces.

One of Accel’s key partners, Theresia Gouw, helped me brainstorm, joining my cadre of professional priests. We had known one another for over a decade (I originally met her as a young founder at Yodlee) and were at similar stages of our careers, so I knew she could identify personally with my career quandaries. Like me, Theresia was pregnant with her next child and at a similar life stage — yet another commonality.

Cropped photo a photo of author Sukhinder Singh Cassidy

Image Credits: Sukhinder Singh Cassidy

While at Accel, I spent a disproportionate amount of time testing my macro thesis that online shopping was about to explode in new ways. I had seen the rise of e-tailers at Google (many of these companies, such as eBay and Amazon, were Google’s largest advertisers at the time), but many of the leading e-commerce sites like Amazon and Zappos still had a utilitarian feel to them.

Meanwhile, new fashion and décor e-commerce sites such as Rent the Runway, Gilt, Houzz, Wayfair and One Kings Lane were popping up everywhere and growing rapidly.

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