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    My big jump: Sukhinder Singh Cassidy’s CEO journey – TechSwitch

    Sukhinder Singh Cassidy
    Contributor

    Sukhinder Singh Cassidy based theBoardrecord, a premium expertise market that helps various leaders get found for board and government alternatives. A know-how government and entrepreneur, board member and investor, she has 25 years of expertise founding and serving to to scale firms, together with Google, Amazon and Yodlee.

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    After listening to others pitch me a number of totally different job alternatives whereas nonetheless at Google in 2008, it turned clear to me that I might make a greater determination if I might absolutely discover the bigger panorama of latest firms rising in Silicon Valley.
    I had spent the final a number of years specializing in Google’s enterprise exterior the U.S., and I truthfully felt out of contact with the startup world. Beyond my purpose of changing into a CEO of my very own firm, I had two different ambitions: I wished to assist construct a terrific shopper service that might delight individuals (probably in e-commerce) and I wished to construct additional wealth for myself and my household.
    To higher consider my choices, I made the choice to give up Google first and discover a technique to examine the broader ecosystem of firms earlier than selecting the place to go. Resolved to provide myself a “blank slate” earlier than making a closing selection, I left Google after I was three months pregnant and joined Accel Partners, a prime Silicon Valley enterprise capital agency and an investor in my earlier startup, in a brief function as CEO-in-residence.
    In the months that adopted, I helped Accel consider funding alternatives throughout all kinds of digital sectors, with a selected give attention to e-commerce, taking the chance to review these firms I’d be a part of or consider ranging 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 “Choose Possibility,” on Twitter Spaces.
    One of Accel’s key companions, Theresia Gouw, helped me brainstorm, becoming a member of my cadre {of professional} monks. We had identified each other for over a decade (I initially met her as a younger founder at Yodlee) and had been at related phases of our careers, so I knew she might establish personally with my profession quandaries. Like me, Theresia was pregnant along with her subsequent youngster and at the same life stage — one more commonality.
    Image Credits: Sukhinder Singh Cassidy
    While at Accel, I spent a disproportionate period of time testing my macro thesis that on-line buying was about to blow up in new methods. I had seen the rise of e-tailers at Google (many of those firms, similar to eBay and Amazon, had been Google’s largest advertisers on the time), however most of the main e-commerce websites like Amazon and Zappos nonetheless had a utilitarian really feel to them.
    Meanwhile, new style and décor e-commerce websites similar to Rent the Runway, Gilt, Houzz, Wayfair and One Kings Lane had been popping up in every single place and rising quickly. These websites sought to faucet right into a extra aspirational and entertainment-oriented form of buying expertise and transfer it on-line.
    Expert buyers like Accel and others had been funding them, and my very own observations recommended that this space would yield one other large wave of on-line shopper progress. These way of life classes of buying additionally appealed to me personally; I used to be the goal buyer for a lot of of them.
    I began to work on an thought for a brand new e-commerce service, a luxurious model of eBay, whereas listening to the pitches of each e-commerce firm that was searching for funding and speaking to a number of that wanted early-stage CEOs. I continued to take heed to non-e-commerce pitches as properly, merely to provide myself some extent of reference for evaluating on-line buying alternatives.
    At Yodlee and Google, I had been fortunate sufficient to work with extremely good and proficient individuals who shared my values, and I wished to do the identical at my subsequent enterprise.
    I wished to work with nice buyers, too, and luckily I had the power both to work with Accel-funded firms, begin my very own or leverage different investor relationships I’d developed. I hung out with a number of firm founders to attempt to discern who they had been as leaders, along with what they had been engaged on.
    By this level in my profession, I had a reasonably clear thought of my very own superpowers and values, so I appeared to search out firms that might benefit from my distinctive items and whose founders or senior leaders had strengths complementary to mine.
    Specifically, I hoped to affix an organization with a really sturdy engineering and product administration tradition that wanted a CEO with technique, imaginative and prescient, enterprise growth, fundraising and team-building experience. Applying these standards, I turned down a number of alternatives at firms whose founders had talent units too just like mine, reasoning that this overlap would possibly result in battle if I ever turned CEO.
    Finally, I used my time at Accel to assume lengthy and arduous concerning the dangers I might absorb changing into a startup CEO and whether or not I might afford to fail. My largest danger by far was ego- and reputation-related. Mindful of how precarious early-stage startups are, I feared that I would depart a profitable function as a worldwide government solely to endure a really massive and visual failure. But the extra I considered this, I confronted this ego danger head-on and concluded that my repute as an government from Google would hopefully be sturdy sufficient to outlive one failure if it got here to that.
    The private dangers of taking over a startup CEO function felt totally different however not higher than these related to my job at Google. While I knew that serving as a first-time CEO whereas having one other new child at residence (my son Kieran) can be immensely anxious, I might possible profit from now not touring world wide for days and weeks on finish and dealing throughout a number of time zones, as I had beforehand.
    Last, I evaluated the monetary dangers of potential strikes. Although my startup fairness would have unsure worth for a very long time, I judged this a danger price taking, given how excited I’d really feel to have extra influence and accountability as CEO. While I misplaced a big monetary bundle in selecting to depart Google and switching to a startup wage, I might pay the payments at residence whereas digging into my financial savings solely barely. Under these situations, I used to be ready to make the leap.
    In early 2010, nearly a 12 months after I left Google, I lastly discovered the appropriate alternative and determined to affix style know-how startup Polyvore as its full-time CEO. A precursor to Pinterest, Polyvore was primarily based on the concept that ladies might “clip” on-line photos to create style and décor thought boards digitally that had been immediately “shoppable.”
    Millions of younger ladies (together with influencers) had been already utilizing the service and cherished it. The founding staff was led by a rock star engineer, Pasha Sadri, together with three different product and know-how of us he recruited from the likes of Yahoo and Google.
    Pasha was identified for his intelligence, and we had related informally through the years for espresso, every time having nice discussions about enterprise technique. In truth, Polyvore twice earlier than had tried to recruit me to turn into its CEO, as soon as after I was at Google and once more after I departed that firm in 2008. Back then, I’d spent a productive afternoon with the founding staff, serving to them assume by their enterprise mannequin. I additionally knew Peter Fenton, one among Silicon Valley’s most profitable buyers and a number one funder of the corporate. Peter was the one who first launched me to Polyvore and who continued afterward to passively courtroom me.
    Having spent a lot time exploring my choices from a number of angles, I used to be now poised to make a terrific determination. I felt satisfied that e-commerce was beginning its subsequent wave of progress, and felt excited to be a part of it.
    Within that imaginative and prescient, Polyvore was among the many firms greatest positioned to succeed, and I knew I might contribute in vital methods to constructing a service that might delight thousands and thousands. I used to be impressed with the strengths of Polyvore’s founder and buyers and anticipated that I might be capable to complement their efforts properly. Recognizing that my success as a startup CEO hinged on my relationships with the founder and board, I had additionally invested time to get to know them.
    Meanwhile, I had confronted my concern demons, taking monetary danger however negotiating my provide aggressively to account for draw back eventualities I imagined, and coming to grips with my ego danger. With all this work in place, I lastly jumped.
    After managing a multibillion-dollar revenue and loss and main a 2,000-person staff at Google, I turned the newly minted CEO of a 10-person style startup in February 2010.
    As we tee up the larger decisions in our careers, all of us face essential moments of determination. No selection we make can be good, and all of the frameworks on the planet received’t eradicate danger totally. But we don’t want perfection or freedom from danger. We simply must take the following step.
    By selecting thoughtfully, utilizing all of the instruments at our disposal to maximise our upside and anticipate our draw back, we will grasp the alternatives obtainable to us whereas equipping ourselves to deal with no matter challenges actuality throws our manner.
    Excerpted from “Choose Possibility: Take Risks and Thrive (Even When You Fail)” by Sukhinder Singh Cassidy. Copyright © 2021 by Sukhinder Singh Cassidy. Published and reprinted by permission of Mariner Books/Houghton Mifflin Harcourt. All rights reserved.

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