My Big Leap: 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 startups emerging in Silicon Valley.

I had spent the last few years concentrating on the Google business outside of the US, and honestly, I felt out of touch with the startup world. Beyond my goal of becoming CEO of my own company, 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 generate more wealth for myself and my family. . .

To better evaluate my options, I made the decision to leave Google first and find a way to study the broader ecosystem of companies before choosing where to go. Determined to blank out before making a final decision, I left Google when I was three months pregnant and joined Accel Partners, one of Silicon Valley’s leading venture capital firms and investor in my previous startup, in a temporary position. as CEO. -in residence.

In the following months, I helped Accel evaluate investment opportunities in a wide variety of digital sectors, with a particular focus on e-commerce, taking the opportunity to study the companies I could join or think about starting from scratch.


Thursday, August 19 at 2 pm PDT / 5 pm EDT / 9 pm UTC

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


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

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-retailers on Google (many of these companies, like eBay and Amazon, were Google’s largest advertisers at the time), but many of the leading e-commerce sites like Amazon and Zappos still had a feel. utilitarian. to them.

Meanwhile, new fashion and decor ecommerce sites like Rent the Runway, Gilt, Houzz, Wayfair, and One Kings Lane were popping up everywhere and growing fast. These sites were looking to take advantage of a more aspirational and entertainment-oriented type of shopping experience and move it online.

Savvy investors like Accel and others were funding them, and my own observations suggested that this area would produce another big wave of online consumer 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 e-commerce service, a deluxe version of eBay, while listening to the pitches of all the e-commerce companies seeking financing and speaking with several that needed early stage CEOs. I continued to listen to non-eCommerce releases as well, simply to give myself a benchmark for evaluating online shopping opportunities.

At Yodlee and Google, I was fortunate to work with incredibly smart and talented people who shared my values, and I wanted to do the same in my next company.

I also wanted to work with large investors, and fortunately had the ability to work with Accel-funded companies, start my own, or take advantage of other investor relationships that I had developed. I spent time with various company founders to try to discern who they were as leaders, as well as what they were working on.

At this point in my career, I had a pretty good idea of ​​my own superpowers and values, so I looked for companies that could make the most of my unique gifts and whose founders or senior leaders had complementary strengths to mine.

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

Finally, I used my time at Accel to think carefully about the risks I would take in becoming CEO of a startup and whether I could afford to fail. My biggest risk by far was related to ego and reputation. Aware of how precarious early-stage startups are, I feared leaving a successful position as a global executive only to suffer a very large and visible failure. But the more I thought about this, the more I faced this selfish risk head-on and concluded that my reputation as a Google executive would hopefully be strong enough to survive failure if it came to that.

The personal risks of taking on a startup CEO role felt different, but not greater, than those associated with my work at Google. While I knew that serving as CEO for the first time while having another newborn at home (my son Kieran) would be immensely stressful, it would probably benefit me from no longer traveling the world for days and weeks and working in multiple time zones. , as he had done previously.

Finally, evaluate the financial risks of possible movements. Although my initial capital would be of uncertain value for a long time, I considered this a risk worth taking, given how excited I would be to have more impact and responsibility as CEO. While I lost a huge financial package by choosing to leave Google and switch to a starting salary, I was able to pay the bills at home while digging into my savings just a little bit. In these conditions, he was ready to make the leap.

In early 2010, almost a year after leaving Google, I finally found the right opportunity and decided to join fashion tech startup Polyvore as its full-time CEO. A forerunner of Pinterest, Polyvore was built on the idea that women could “crop” images online to create digitally “shoppable” fashion and decorating idea boards.

Millions of young women (including influencers) were already using the service and they loved it. The founding team was led by a rock star engineer, Pasha Sadri, along with three other technology and product people he recruited from companies like Yahoo and Google.

Pasha was known for his intelligence, and we had informally hooked up over the years for coffee, and each time we had great discussions about business strategy. In fact, Polyvore had tried twice before to recruit me to become their CEO, once when I was at Google and again when I left that company in 2008. Back then, I had spent a productive afternoon with the founding team, helping them think through its business model. I also met Peter Fenton, one of the most successful investors in Silicon Valley and one of the main funders of the company. Peter was the one who first introduced me to Polyvore and who continued to passively court me afterward.

Having spent so much time exploring my options from multiple angles, I was now ready to make a big decision. He was convinced that e-commerce was starting its next wave of growth and he was excited to be a part of it.

Within that vision, Polyvore was among the companies best positioned to succeed, and it knew it could make a significant contribution to building a service that would delight millions. I was impressed by the strengths of the Polyvore founder and investors and anticipated that I could nicely complement their efforts. Recognizing that my success as the CEO of a startup depended on my relationships with the founder and the board, I had also invested time to get to know them.

In the meantime, I had faced my demons of fear, taking a financial risk but aggressively negotiating my offer to account for the negative scenarios I imagined and taking my ego risk. With all this work in place, I finally jumped.

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

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

By choosing carefully, using all the tools at our disposal to maximize our advantages and anticipate our disadvantages, we can take advantage of the opportunities available to us while equipping ourselves to handle whatever challenges reality throws at us.

Taken from “Choose the possibility: take risks and prosper (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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