My extensive jump: Sukhinder Singh Cassidy’s CEO creep

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Sukhinder Singh Cassidy Contributor

Sukhinder Singh Cassidy founded theBoardlist, a top rate skill market that helps various leaders get stumbled on for board and govt alternatives. A skills govt and entrepreneur, board member and investor, she has 25 years of skills founding and serving to to scale companies, including Google, Amazon and Yodlee.

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After being attentive to others pitch me a few different job alternatives whereas nonetheless at Google in 2008, it modified into sure to me that I would fabricate a closer resolution if I might maybe well utterly explore the upper landscape of fresh companies emerging in Silicon Valley.

I had spent the final loads of years specializing in Google’s commercial out of doors the U.S., and I in truth felt out of contact with the startup world. Past my aim of becoming a CEO of my possess firm, I had two different ambitions: I wished to lend a hand device a gargantuan client carrier that would delight folks (doubtlessly in e-commerce) and I wished to device extra wealth for myself and my family.

To higher attend in mind my choices, I made the resolution to forestall Google first and get a mode to head attempting the broader ecosystem of companies earlier than choosing the place to head. Resolved to present myself a “easy slate” earlier than making a final decision, I left Google when I was once three months pregnant and joined Accel Companions, a top Silicon Valley project capital company and an investor in my outdated startup, in a momentary characteristic as CEO-in-characteristic.

In the months that adopted, I helped Accel attend in mind investment alternatives all the way thru a huge number of digital sectors, with a particular point of curiosity on e-commerce, taking the different to head attempting those companies I might maybe well be a half of or judge 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, creator of “Rep Possibility,” on Twitter Areas.


Considered one of Accel’s key partners, Theresia Gouw, helped me brainstorm, becoming a member of my cadre of expert monks. We had identified every other for over a decade (I initially met her as a young founder at Yodlee) and had been at identical phases of our careers, so I knew she might maybe well title personally with my occupation quandaries. Treasure me, Theresia was once pregnant along with her subsequent runt one and at a identical life stage — but one other commonality.

Cropped photo a photo of author Sukhinder Singh Cassidy

Image Credits: Sukhinder Singh Cassidy

While at Accel, I spent a disproportionate duration of time checking out my macro thesis that on-line attempting was once about to blow up in fresh ways. I had seen the upward thrust of e-tailers at Google (many of those companies, equivalent to eBay and Amazon, had been Google’s greatest advertisers on the time), nonetheless most of the main e-commerce web sites delight in Amazon and Zappos nonetheless had a utilitarian with out a doubt feel to them.

Meanwhile, fresh type and décor e-commerce web sites equivalent to Rent the Runway, Gilt, Houzz, Wayfair and One Kings Lane had been popping up in every single site and rising without be conscious. These web sites sought to faucet exact into a extra aspirational and entertainment-oriented form of attempting skills and pass it on-line.

Expert investors delight in Accel and others had been funding them, and my possess observations suggested that this command would yield one other extensive wave of on-line client growth. These standard of living classes of attempting also appealed to me personally; I was once the aim buyer for many of them.

I started to work on an notion for a brand fresh e-commerce carrier, a luxurious model of eBay, whereas being attentive to the pitches of every e-commerce firm that was once attempting for funding and talking to loads of that wanted early-stage CEOs. I continued to hear to non-e-commerce pitches as successfully, merely to present myself a degree of reference for evaluating on-line attempting alternatives.

At Yodlee and Google, I had been lucky ample to work with incredibly orderly and talented folks who shared my values, and I wished to realize the same at my subsequent project.

I wished to work with gargantuan investors, too, and luckily I had the capability either to work with Accel-funded companies, open up my possess or leverage different investor relationships I’d developed. I spent time with a few firm founders to strive to discern who they had been as leaders, as well to to what they had been working on.

By this point in my occupation, I had a pretty sure notion of my possess superpowers and values, so I regarded to get companies that will well fabricate essentially the most of my queer presents and whose founders or senior leaders had strengths complementary to mine.

Particularly, I hoped to hitch a firm with a actually solid engineering and product management culture that wanted a CEO with procedure, vision, commercial style, fundraising and team-constructing skills. Applying these requirements, I modified into down loads of alternatives at companies whose founders had skill gadgets too equivalent to mine, reasoning that this overlap might maybe well result in battle if I ever modified into CEO.

At final, I dilapidated my time at Accel to mediate prolonged and difficult regarding the risks I would soak up becoming a startup CEO and whether or now no longer I might maybe well get the money for to fail. My greatest fret by far was once ego- and repute-linked. Aware of how precarious early-stage startups are, I feared that I would disappear away a a success characteristic as a worldwide govt utterly to endure a actually astronomical and seen failure. But the extra I idea about this, I confronted this ego fret head-on and concluded that my repute as an govt from Google would optimistically be solid ample to continue to exist one failure if it came to that.

The non-public risks of taking on a startup CEO characteristic felt different nonetheless now no longer bigger than those linked to my job at Google. While I knew that serving as a prime-time CEO whereas having one other fresh child at dwelling (my son Kieran) might maybe well be immensely disturbing, I would likely make the most of no longer traveling round the arena for days and weeks on stop and dealing all the way thru a few time zones, as I had beforehand.

Closing, I evaluated the financial risks of likely moves. Although my startup equity would have uncertain price for a actually prolonged time, I judged this a fret worth taking, given how angry I’d with out a doubt feel to have extra impression and responsibility as CEO. While I lost a astronomical financial equipment in choosing to leave Google and switching to a startup salary, I might maybe well pay the bills at dwelling whereas digging into my financial savings utterly moderately. Underneath these conditions, I was once ready to manufacture the soar.

In early 2010, almost a year after I left Google, I at final stumbled on essentially the most moving form different and made up our minds to hitch type skills startup Polyvore as its fleshy-time CEO. A precursor to Pinterest, Polyvore was once per the foundation that ladies folks might maybe well “clip” on-line images to originate type and décor notion boards digitally that had been right away “shoppable.”

Millions of younger ladies folks (including influencers) had been already the utilization of the carrier and cherished it. The founding team was once led by a rock superstar engineer, Pasha Sadri, along with three different product and skills folks he recruited from the likes of Yahoo and Google.

Pasha was once identified for his intelligence, and we had linked informally over time for espresso, whenever having gargantuan discussions about commercial procedure. In actuality, Polyvore twice earlier than had tried to recruit me to change into its CEO, once when I was once at Google and once more when I departed that firm in 2008. Advantage then, I’d spent a productive afternoon with the founding team, serving to them mediate thru their commercial mannequin. I also knew Peter Fenton, one of Silicon Valley’s most a success investors and a main funder of the firm. Peter was once the one who first launched me to Polyvore and who continued afterward to passively court me.

Having spent so worthy time exploring my choices from a few angles, I was once now poised to manufacture a gargantuan resolution. I felt delighted that e-commerce was once starting its subsequent wave of growth, and felt angry to be share of it.

Within that vision, Polyvore was once among the companies most efficient positioned to prevail, and I knew I might maybe well make contributions in predominant ways to constructing a carrier that would delight millions. I was once impressed with the strengths of Polyvore’s founder and investors and anticipated that I might maybe well be ready to enrich 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 get to know them.

Meanwhile, I had confronted my fright demons, taking financial fret nonetheless negotiating my provide aggressively to yarn for downside scenarios I imagined, and coming to grips with my ego fret. With all this work in site, I at final jumped.

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

As we tee up the greater picks in our careers, all of us face extreme moments of resolution. No decision we fabricate will almost definitely be most moving, and the complete frameworks on the planet received’t get rid of fret utterly. But we don’t want perfection or freedom from fret. We factual have to possess the next circulation.

By choosing thoughtfully, the utilization of the complete tools at our disposal to maximise our upside and count on our downside, we will present you with the selection to make your mind up on the alternatives available to us whereas equipping ourselves to residence regardless of challenges actuality throws our way.

Excerpted from “Rep Possibility: Retract 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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