Sukhinder Singh Cassidy, my big leap: My CEO journey

While I was still working at Google, in 2008 I heard several different opportunities and it became obvious to me that I’d make better decisions if I had the opportunity to explore all of Silicon Valley’s new businesses.

I felt disconnected from the startup community after spending the past several years solely on Google’s U.S. business. My goal was to become a CEO for my company. I also had other goals: To help create a fantastic consumer service, which would delight others (potentially through e-commerce), and to increase my wealth for my family and me.

In order to better assess my options, the first thing I did was to leave Google and go to work studying the larger ecosystem before making a decision on where to move. In order to have a blank slate before I made a decision, I quit Google while I was pregnant with my third child. I joined Accel Partners as a CEO-in residence at a leading Silicon Valley venture capital company.

The months following, Accel helped me evaluate investment opportunities in a variety of digital sector, with a special focus on ecommerce. I also took the time to examine companies that I may join, or consider starting.

This Thursday, August 19, at 2:05 p.m. PDT/5:45 p.m. ET/9 p.m. UT

Danny Crichton, Managing Editor of The Guardian will be interviewing Sukhinder S. Cassidy on Twitter Spaces.

Theresia, one of Accel’s most important partners, was a key player in helping me to brainstorm and join my group of priests. Our friendship lasted over 10 years. I first met Theresia at Yodlee as a young founder. We were both at the same stage in our careers so it was easy for me to identify with her career problems. Theresia, like me was also pregnant and in a similar stage of her life — another commonality.

Image Credits: Sukhinder Singh Cassidy

My macro thesis about online shopping was in rapid development, which I tested while at Accel. Although I was able to see the growth of etailers at Google, many of these companies (such as eBay and Amazon) were Google’s biggest advertisers at that time, most of the top ecommerce websites like Zappos and Amazon still felt utilitarian.

New e-commerce websites for fashion and décor such as Rent The Runway, Gilt and Houzz were appearing all over the place and expanding rapidly. These sites sought to tap into a more aspirational and entertainment-oriented kind of shopping experience and move it online.

They were funded by experts like Accel, as well as others. My own observations suggest that there will be another surge in online customer growth. This lifestyle category of shopping appealed to my personal tastes; many of these were targeted at me.

While listening to pitches from every ecommerce company looking to raise capital and speaking to many that were seeking early-stage executives, I began to develop an idea for a new online e-commerce platform. To give me a reference point for online shopping, I also listened to pitches from non-ecommerce companies.

Yodlee, Google and other companies, I was fortunate enough to have worked with people who were incredibly talented and shared my values. I wanted the same for my next venture.

Working with top investors was something I wanted. Fortunately, I could either work with Accel-funded businesses, create my own company, or use existing investor relationships. To learn more about the founders of different companies, I met with them to get a sense for who they were and what they were doing.

At this stage in my career I was pretty sure of what my superpowers were and my values. I began to look for companies that would make the best of me and have founders or leaders with complementary strengths.

I was looking for a company that had strong product and engineering management cultures and needed a leader with vision, strategy, team building, fundraising, and business development expertise. These criteria were used to reject several offers from companies with founders who had similar skill sets to my own. I feared that the overlap could lead to conflicts if I became CEO.

I spent my time at Accel thinking long and deeply about what risks I’d take as a CEO of a startup and whether or not I was able to afford failure. Ego- and reputation-related risks were my biggest concerns. Knowing how fragile early-stage startups can be, I was afraid that my role as global executive would end in failure. The more I considered this issue, the more I realized that I would be able to endure one failure as a Google executive.

My personal risk of being a CEO at a startup was different from my work at Google. Although I was aware that being a new CEO and having a newborn (Kieran), would prove to be extremely stressful, it would also mean I wouldn’t have to travel around the globe for weeks and work in different time zones.

The financial risk of possible moves was last. In spite of the fact that my startup equity was likely to lose value over time, this seemed like a worthwhile risk given my excitement about being a CEO and having more responsibility. Although I did lose a significant financial package by leaving Google to switch to a startup income, I was able to pay my bills from home and only dip into my savings. These conditions were favorable and I felt ready to take the plunge.

Nearly a full year ago, after leaving Google, I decided to take up the role of CEO at fashion startup Polyvore. Polyvore, a precursor to Pinterest was founded on the notion that women could “clip” online photos to make fashion and decor boards that were digitally “shoppable”.

The service was loved by millions of young girls, including influencers. Pasha Sadri (a rock star engineer) was the founder of the team. He also recruited three technology and product people from companies like Yahoo and Google.

Pasha was well-known for his intelligence. We had a long and informal relationship over coffee. Each time we discussed business strategy, Pasha was a great conversationalist. Polyvore had twice tried to hire me as its CEO before, once while I was working at Google, and again after I left that company. The founding team had spent an afternoon working with me to develop their business plan. Peter Fenton was also a successful investor and major funder in Silicon Valley. Peter introduced me to Polyvore, and he continued to court me passively afterward.

After spending so many hours exploring all options, it was time to finally make the right decision. It was clear that ecommerce was on the cusp of its next great wave of growth and I felt pleased to have been a part of it.

Polyvore, based on that vision, was one of the most well-positioned companies to succeed. I believed I had an important role to play in building a service that delights millions. Polyvore’s investors and founder impressed me and I knew that I could complement them well. Knowing that success for a startup CEO was dependent on the relationships I have with founders and boards, I took time to get to understand them.

I was facing my fears and taking financial risks. I also aggressively negotiated my offer to cover any potential downsides. I came to terms with my ego risk. After all of this, I was finally ready to jump.

In February 2010, I was re-elected as the CEO of a fashion startup with 10 employees.

We all have to make difficult decisions as we attempt to make the best choices for our career. There is no perfect choice, and there are many frameworks that won’t completely eliminate risks. We don’t have to be perfect or free from risks. It’s enough to move on.

We can maximize our upside by choosing wisely and anticipating our downfall. This will allow us to grasp all that is possible while also equipping ourselves for dealing with any challenges we face.

This excerpt is from Sukhinder S. Cassidy’s “Choose Possibility”: Take risks and thrive (Even when you fail) Copyright (c), 2021 Sukhinder S. Cassidy This article was published and reprinted with permission from Mariner Books/Houghton Mifflin Harcourt. All rights are reserved.

Publited at Sun, 15 August 2021 16:44.35 +0000

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