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Sukhinder Singh Cassidy’s CEO journey – TechCrunch


After listening to others pitch me a couple of totally different job alternatives whereas nonetheless at Google in 2008, it grew to become clear to me that I’d make a greater determination if I may totally discover the bigger panorama of latest corporations rising in Silicon Valley.

I had spent the final a number of years specializing in Google’s enterprise outdoors the U.S., and I truthfully felt out of contact with the startup world. Beyond my aim of turning into a CEO of my very own firm, I had two different ambitions: I needed to assist construct an important shopper service that will delight individuals (doubtlessly in e-commerce) and I needed to construct additional wealth for myself and my household.

To higher consider my choices, I made the choice to stop Google first and discover a option to examine the broader ecosystem of corporations earlier than selecting the place to go. Resolved to offer myself a “blank slate” earlier than making a closing alternative, I left Google once 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 deal with e-commerce, taking the chance to review these corporations I would be 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, writer 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 recognized each other for over a decade (I initially met her as a younger founder at Yodlee) and had been at comparable phases of our careers, so I knew she may determine personally with my profession quandaries. Like me, Theresia was pregnant along with her subsequent baby and at an analogous life stage — one more commonality.

Cropped photo a photo of author Sukhinder Singh Cassidy

Image Credits: Sukhinder Singh Cassidy

While at Accel, I spent a disproportionate period of time testing my macro thesis that online procuring was about to blow up in new methods. I had seen the rise of e-tailers at Google (many of those corporations, akin 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 akin 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 sort of procuring expertise and transfer it online.

Expert buyers like Accel and others had been funding them, and my very own observations urged that this space would yield one other large wave of online shopper progress. These way of life classes of procuring 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 effectively, merely to offer myself a degree of reference for evaluating online procuring alternatives.

At Yodlee and Google, I had been fortunate sufficient to work with extremely good and gifted individuals who shared my values, and I needed to do the identical at my subsequent enterprise.

I needed to work with nice buyers, too, and luckily I had the flexibility both to work with Accel-funded corporations, 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 seemed to seek out corporations that would benefit from my distinctive presents 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 corporations whose founders had ability units too much like mine, reasoning that this overlap would possibly result in battle if I ever grew to become CEO.

Finally, I used my time at Accel to suppose lengthy and onerous in regards to the dangers I’d absorb turning into a startup CEO and whether or not I may 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 thought of this, I confronted this ego danger head-on and concluded that my popularity 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 up 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) could be immensely irritating, I’d doubtless profit from 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 value taking, given how excited I’d really feel to have extra impression and duty as CEO. While I misplaced a big monetary package deal in selecting to go away Google and switching to a startup wage, I may 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 yr after I left Google, I lastly discovered the best alternative and determined to affix style expertise startup Polyvore as its full-time CEO. A precursor to Pinterest, Polyvore was based mostly on the concept girls may “clip” online pictures to create style and décor thought boards digitally that had been immediately “shoppable.”

Millions of younger girls (together with influencers) had been already utilizing the service and liked it. The founding workforce was led by a rock star engineer, Pasha Sadri, together with three different product and expertise people he recruited from the likes of Yahoo and Google.

Pasha was recognized for his intelligence, and we had linked informally over time for espresso, every time having nice discussions about enterprise technique. In reality, Polyvore twice earlier than had tried to recruit me to change into its CEO, as soon as once I was at Google and once more once I departed that firm in 2008. Back then, I’d spent a productive afternoon with the founding workforce, serving to them suppose via their enterprise mannequin. I additionally knew Peter Fenton, considered one of 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 an important 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 corporations greatest positioned to succeed, and I knew I may contribute in vital methods to constructing a service that will delight thousands and thousands. I used to be impressed with the strengths of Polyvore’s founder and buyers and anticipated that I’d 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 worry demons, taking monetary danger however negotiating my supply aggressively to account for draw back situations 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 workforce at Google, I grew to become 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 vital moments of determination. No alternative we make shall be good, and all of the frameworks on the planet received’t remove danger completely. But we don’t want perfection or freedom from danger. We simply must take the subsequent step.

By selecting thoughtfully, utilizing all of the instruments at our disposal to maximise our upside and anticipate our draw back, we are able to grasp the alternatives obtainable to us whereas equipping ourselves to deal with no matter challenges actuality throws our approach.

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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