Sukhinder Singh Cassidy’s CEO journey – TechCrunch

After listening to others introduce me to a few different job opportunities while I was 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 emerging companies in Silicon Valley.

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

To better assess my options, I first made the decision to quit Google and find a way to study the larger business ecosystem before deciding where to go. Determined to give myself a “blank slate” before making a final choice, I left Google when I was three months pregnant and joined Accel Partners, one of the leading venture capital firms in the world. Silicon Valley and investor in my previous startup, in a temporary role of CEO -in residence.

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


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

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


One of Accel’s key partners, Theresia Gouw, helped me reflect and join my group of professional priests. We had known each other for over a decade (I originally met her as a young founder at Yodlee) and were at similar stages in our careers, so I knew she could relate to me personally. career dilemmas. Like me, Theresia was pregnant with her next child and at a similar stage of her life – yet another common thread.

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-merchants at Google (many of these companies, like eBay and Amazon, were Google’s biggest advertisers at the time), but many of the major e-commerce sites like Amazon and Zappos still had a utilitarian feel. for them.

Meanwhile, new fashion and home decor e-commerce sites such as Rent the Runway, Gilt, Houzz, Wayfair, and One Kings Lane were popping up everywhere and growing rapidly. These sites were looking to harness a more ambitious, entertainment-focused shopping experience and bring it online.

Expert investors like Accel and others were funding them, and my own observations suggested that this area would see another big wave of online consumption growth. These shopping lifestyle categories also appealed to me personally; I was the target customer for many of them.

I started working on an idea for a new ecommerce service, a deluxe version of eBay, while listening to the arguments of every ecommerce business looking for funding and chatting with several who needed funding. Start-up CEO. I also continued to listen to non-e-commerce pitches, just to give myself a point of reference to assess online shopping opportunities.

At Yodlee and Google, I had been fortunate enough to work with some incredibly smart and talented people who shared my values, and I wanted to do the same on my next venture.

I also wanted to work with large investors and luckily I had the opportunity to work with companies funded by Accel, build my own, or leverage other investor relationships that I had developed. I spent time with several company founders trying to discern who they were as leaders, in addition to what they were working on.

At this point in my career, I had a pretty clear idea of ​​my own superpowers and values, so I looked to find companies that could make the most of my unique gifts and which founders or top executives. had strengths complementary to mine.

Specifically, I was hoping to join a company with a very strong engineering and product management culture that needed a CEO with expertise in strategy, vision, business development, fundraising, and team building. Applying these criteria, I turned down several opportunities in companies whose founders had skills too similar to mine, believing that this overlap could lead to conflicts if I ever became CEO.

Finally, I used my time at Accel to think long and hard about the risks I would take in becoming CEO of a startup and whether I could afford to fail. By far my biggest risk was with ego and reputation. Aware of the precariousness of startups in the start-up phase, I was afraid of leaving a successful role as a global executive only to suffer a very significant and visible failure. But the more I thought about it, the more I faced this ego risk and concluded that my reputation as a Google executive would hopefully be strong enough to survive a failure if it did.

The personal risks of taking on a startup CEO role seemed different but no greater than those associated with my work at Google. While I knew that being a CEO for the first time while having another newborn baby at home (my son Kieran) would be extremely stressful, I would probably benefit from not traveling the world for days and weeks. work across multiple time zones. , as I had done before.

Finally, I assessed the financial risks of potential moves. Although my start-up capital has been of uncertain value for a long time, I felt this risk was worth taking, given how happy I would love to have more impact and responsibility as a CEO. . While I lost a big financial bundle by choosing to quit Google and switch to a start-up salary, I was able to pay the bills at home while only slightly dipping into my savings. Under these conditions, I was ready to take the plunge.

In early 2010, almost a year after leaving Google, I finally found the right opportunity and decided to join fashion tech startup Polyvore as a full-time CEO. A pioneer of Pinterest, Polyvore was based on the idea that women could “clip” images online to digitally create arrays of fashion and decor ideas that were instantly “purchasable”.

Millions of young women (including influencers) were already using and adoring the service. The founding team was led by rock star engineer Pasha Sadri along with three other product and tech specialists he recruited from Yahoo and Google.

Pasha was known for his intelligence, and we had logged in informally over the years for coffee, each time having great discussions about business strategy. In fact, Polyvore had tried twice to recruit me to become its CEO, once when I was at Google and once when I left that company in 2008. At the time, I had an after -productive midday with the founding team, helping them to think through their economic model. I also knew Peter Fenton, one of Silicon Valley’s most successful investors and one of the company’s main backers. Peter is the one who first introduced me to Polyvore and then continued to passively court me.

After spending so much time exploring my options from multiple angles, I was now on the verge of making a great decision. I was convinced that e-commerce was entering its next wave of growth and I was excited to be a part of it.

In this vision, Polyvore was among the companies best positioned to succeed, and I knew I could make a significant contribution to creating a service that would delight millions of people. I was impressed by the strengths of Polyvore’s founder and investors and anticipated that I would be able to complement their efforts well. Recognizing that my success as a startup CEO rested on my relationships with the founder and the board, I had also invested time in getting to know them.

During this time, I had faced my demons of fear, taking financial risks but aggressively negotiating my offer to accommodate the negative scenarios I was imagining, and facing my ego risk. . With all of this work in place, I finally jumped in.

After managing a multibillion-dollar profit and loss account and leading a 2,000-person team at Google, I became the new CEO of a 10-person fashion startup in February 2010.

As we make bigger choices in our careers, we all face critical decision moments. No choice we make will be perfect, and not all frameworks in the world will eliminate risk entirely. But we don’t need perfection or the absence of risk. We just need to take the next step.

By choosing wisely, using all the tools at our disposal to maximize our advantages and anticipate our disadvantages, we can seize the opportunities available to us while equipping ourselves to meet all the challenges that reality has in store for us.

Extract of “Choose the possibility: take risks and thrive (even when you fail) ” by Sukhinder Singh Cassidy. Copyright © 2021 by Sukhinder Singh Cassidy. Published and reprinted with permission from Mariner Books / Houghton Mifflin Harcourt. All rights reserved.


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