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My big jump: Sukhinder Singh Cassidy’s CEO journey

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My big jump: Sukhinder Singh Cassidy’s CEO journey

Sukhinder Singh Cassidy
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Sukhinder Singh Cassidy essentially based theBoardlist, a top rate capacity market that helps diverse leaders in finding figured out for board and govt alternatives. A expertise govt and entrepreneur, board member and investor, she has 25 years of expertise founding and serving to to scale corporations, including Google, Amazon and Yodlee.

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After listening to others pitch me just a few thoroughly different job alternatives whereas quiet at Google in 2008, it was certain to me that I would make a bigger decision if I could maybe well well presumably fully stumble on the bigger panorama of fresh corporations rising in Silicon Valley.

I had spent the last a number of years focusing on Google’s industry launch air the U.S., and I truthfully felt out of touch with the startup world. Beyond my purpose of changing into a CEO of my have firm, I had two thoroughly different ambitions: I wished to merit intention a big user provider that can satisfaction folks (presumably in e-commerce) and I wished to intention further wealth for myself and my family.

To higher evaluate my alternate choices, I made the decision to quit Google first and glean a approach to gaze the wider ecosystem of corporations ahead of picking where to pass. Resolved to present myself a “blank slate” ahead of making a closing likelihood, I left Google when I was three months pregnant and joined Accel Partners, a high Silicon Valley project capital agency and an investor in my outdated startup, in a non permanent intention as CEO-in-location.

Within the months that adopted, I helped Accel evaluate investment alternatives all over a big quantity of digital sectors, with a explicit focal point on e-commerce, taking the different to gaze those corporations I would join or recall to mind starting up 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, creator of “Bear Risk,” on Twitter Spaces.


One amongst Accel’s key companions, Theresia Gouw, helped me brainstorm, joining my cadre of legit priests. We had identified each and every other for over a decade (I firstly met her as a younger founder at Yodlee) and had been at same phases of our careers, so I knew she may maybe well well presumably title personally with my career quandaries. Love me, Theresia was pregnant with her subsequent child and at a same life stage — but one other commonality.

Cropped photo a photo of author Sukhinder Singh Cassidy

Characterize Credit ranking: Sukhinder Singh Cassidy

Whereas at Accel, I spent a disproportionate quantity of time checking out my macro thesis that on-line trying was about to explode in fresh ways. I had seen the upward push of e-tailers at Google (many of these corporations, comparable to eBay and Amazon, had been Google’s largest advertisers on the time), however many of the main e-commerce websites admire Amazon and Zappos quiet had a utilitarian feel to them.

Within the period in-between, fresh fashion and décor e-commerce websites comparable to Rent the Runway, Gilt, Houzz, Wayfair and One Kings Lane had been shooting up in each set and rising fleet. These websites sought to tap into a more aspirational and entertainment-oriented more or less trying expertise and pass it on-line.

Expert investors admire Accel and others had been funding them, and my have observations speedy that this dispute would yield one other big wave of on-line user enhance. These daily life lessons of trying also appealed to me personally; I was the aim customer for loads of of them.

I began to work on an belief for a brand fresh e-commerce provider, a luxurious version of eBay, whereas listening to the pitches of every e-commerce firm that was looking to search out funding and talking to a number of that wished early-stage CEOs. I persevered to be conscious of non-e-commerce pitches as successfully, simply to present myself some extent of reference for evaluating on-line trying alternatives.

At Yodlee and Google, I had been lucky sufficient to work with incredibly orderly and proficient those that shared my values, and I wished to achieve the same at my subsequent project.

I wished to work with big investors, too, and fortunately I had the flexibility both to work with Accel-funded corporations, delivery my have or leverage thoroughly different investor relationships I’d developed. I frolicked with a number of firm founders to buy a take a study to discern who they had been as leaders, to boot to to what they had been working on.

By this point in my career, I had a pretty certain belief of my have superpowers and values, so I looked to search out corporations that will per chance well presumably profit from my new presents and whose founders or senior leaders had strengths complementary to mine.

Specifically, I hoped to affix a firm with a basically sturdy engineering and product administration tradition that wished a CEO with strategy, imaginative and prescient, industry pattern, fundraising and team-constructing expertise. Applying these criteria, I was down a number of alternatives at corporations whose founders had capacity items too much like mine, reasoning that this overlap may maybe well well presumably lead to battle if I ever was CEO.

Sooner or later, I aged my time at Accel to think long and distinguished about the dangers I would absorb turning into a startup CEO and whether or no longer I will come up with the cash for to fail. My biggest likelihood by some distance was ego- and recognition-related. Aware of how precarious early-stage startups are, I feared that I would trail away a profitable intention as a global govt handiest to suffer a basically trim and seen failure. Nonetheless the more I believed about this, I faced this ego likelihood head-on and concluded that my recognition as an govt from Google would with any luck be sturdy sufficient to outlive one failure if it came to that.

The non-public dangers of taking up a startup CEO intention felt thoroughly different however no longer bigger than those related to my job at Google. Whereas I knew that serving as a first-time CEO whereas having one other newborn at dwelling (my son Kieran) can be immensely anxious, I would likely like the aid of now no longer traveling around the globe for days and weeks on discontinuance and working all over a number of time zones, as I had beforehand.

Final, I evaluated the monetary dangers of doable moves. Although my startup fairness would like hazardous rate for a basically very long time, I judged this a likelihood value taking, given how indignant I’d feel to like more impact and duty as CEO. Whereas I lost a trim monetary bundle in picking to pass away Google and switching to a startup salary, I could maybe well well presumably pay the funds at dwelling whereas digging into my financial savings handiest a shrimp little bit of. Below these stipulations, I was challenging to make the bounce.

In early 2010, nearly a One year after I left Google, I finally figured out the proper different and made up our minds to affix fashion expertise startup Polyvore as its chunky-time CEO. A precursor to Pinterest, Polyvore was per the postulate that girls may maybe well well presumably “clip” on-line photos to intention fashion and décor belief boards digitally that had been straight “shoppable.”

Tens of millions of younger girls (including influencers) had been already utilizing the provider and loved it. The founding team was led by a rock star engineer, Pasha Sadri, alongside with three thoroughly different product and expertise of us he recruited from the likes of Yahoo and Google.

Pasha was identified for his intelligence, and we had related informally over the years for espresso, every time having big discussions about industry strategy. Indubitably, Polyvore twice ahead of had tried to recruit me to develop into its CEO, as soon as when I was at Google and all but again when I departed that firm in 2008. Attend then, I’d spent a productive afternoon with the founding team, serving to them think through their industry mannequin. I also knew Peter Fenton, one amongst Silicon Valley’s most profitable investors and a main funder of the firm. Peter was the one who first launched me to Polyvore and who persevered in a while to passively courtroom me.

Having spent so distinguished time exploring my alternate choices from a number of angles, I was now poised to make a big decision. I felt delighted that e-commerce was starting up its subsequent wave of enhance, and felt indignant to be fragment of it.

Within that imaginative and prescient, Polyvore was among the corporations easiest positioned to prevail, and I knew I could maybe well well presumably contribute in well-known ways to constructing a provider that can satisfaction tens of millions. I was impressed with the strengths of Polyvore’s founder and investors and anticipated that I will be in a position to complement their efforts successfully. Recognizing that my success as a startup CEO hinged on my relationships with the founder and board, I had also invested time to in finding to know them.

Within the period in-between, I had faced my alarm demons, taking monetary likelihood however negotiating my provide aggressively to memoir for downside eventualities I imagined, and coming to grips with my ego likelihood. With all this work in space, I finally jumped.

After managing a multibillion-buck profit and loss and main a 2,000-person team at Google, I was the newly minted CEO of a 10-person fashion startup in February 2010.

As we tee up the bigger picks in our careers, we all face severe moments of decision. No likelihood we make will be perfect, and all of the frameworks on this planet won’t assign away with likelihood fully. Nonetheless we don’t want perfection or freedom from likelihood. We goal want to buy the subsequent step.

By picking thoughtfully, utilizing all of the instruments at our disposal to maximise our upside and sit down up for our downside, we should always buy the alternatives on hand to us whereas equipping ourselves to tackle regardless of challenges reality throws our formula.

Excerpted from “Bear Risk: Grab Dangers and Thrive (Even When You Fail)’ by Sukhinder Singh Cassidy. Copyright © 2021 by Sukhinder Singh Cassidy. Printed and reprinted by permission of Mariner Books/Houghton Mifflin Harcourt. All rights reserved.

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My big jump: Sukhinder Singh Cassidy’s CEO journey