My Big Jump: Sukhinder Singh Cassidy’s CEO Journey

Navigating Career Transitions: A Strategic Approach

While still employed at Google in 2008, after considering several job proposals, it became apparent that a comprehensive evaluation of emerging companies within Silicon Valley was necessary for making an informed career decision.

Having dedicated recent years to Google’s international operations, I felt somewhat disconnected from the startup environment. Beyond my aspiration to eventually lead a company as CEO, I harbored two further objectives: to contribute to the creation of a compelling consumer product – potentially within the e-commerce sector – and to enhance my financial standing for myself and my family.

A Period of Exploration and Evaluation

To effectively assess my options, I resolved to resign from Google and dedicate time to studying the broader company landscape before committing to a new role. Determined to approach this with a fresh perspective, I departed Google during my third month of pregnancy and accepted a temporary position as CEO-in-residence at Accel Partners, a prominent Silicon Valley venture capital firm that had previously invested in one of my ventures.

During the subsequent months, I assisted Accel in evaluating potential investments across diverse digital industries, with a particular emphasis on e-commerce. This provided a valuable opportunity to analyze companies I might consider joining or potentially launching independently.

On Thursday, August 19th at 2:00 PM PDT / 5:00 PM EDT / 9:00 PM UTC, Managing Editor Danny Crichton will host an interview with Sukhinder Singh Cassidy, author of “Choose Possibility,” on Twitter Spaces.

Seeking Counsel and Perspective

Accel partner Theresia Gouw proved instrumental in my brainstorming process, becoming a trusted advisor. We had maintained a professional relationship for over a decade – initially connecting when I was a founder at Yodlee – and found ourselves at comparable career stages, allowing for a shared understanding of my professional challenges. Notably, Theresia was also expecting her next child, adding another layer of commonality.

My time at Accel was largely devoted to validating my belief that online retail was poised for significant expansion. I had observed the growth of e-commerce businesses while at Google – companies like eBay and Amazon were major advertisers – but many established sites still lacked a sophisticated user experience.

The Rise of Aspirational E-commerce

Simultaneously, emerging e-commerce platforms specializing in fashion and home décor, such as Rent the Runway, Gilt, Houzz, Wayfair, and One Kings Lane, were gaining traction. These businesses aimed to deliver a more engaging and aspirational shopping experience online.

Leading investors, including Accel, were actively funding these ventures, and my own analysis indicated substantial potential for further growth in these lifestyle categories. Furthermore, these areas aligned with my personal interests, as I identified as a target consumer for many of these services.

While evaluating investment opportunities, I began developing a concept for a new e-commerce service – a luxury marketplace akin to eBay – and engaged with numerous e-commerce companies seeking funding or early-stage leadership. I also continued to assess opportunities outside of e-commerce to maintain a broader perspective.

Throughout my career at Yodlee and Google, I had consistently collaborated with exceptionally talented individuals who shared my core values, and I sought to replicate this dynamic in my next role.

I also prioritized working with reputable investors and had the flexibility to collaborate with Accel-backed companies, launch my own venture, or leverage existing investor relationships. I dedicated time to assessing the leadership qualities of various company founders.

Defining Personal Criteria for Success

By this stage, I had a clear understanding of my strengths and values, and I aimed to align with organizations that could maximize my contributions and benefit from complementary skill sets within their leadership teams.

Specifically, I sought a company with a robust engineering and product management culture that required a CEO with expertise in strategy, vision, business development, fundraising, and team building. Consequently, I declined opportunities at companies where the founders possessed skill sets too similar to my own, anticipating potential conflicts.

My time at Accel also prompted a thorough assessment of the risks associated with assuming a startup CEO role, and my capacity to withstand potential setbacks. The most significant risk centered on my professional reputation. I acknowledged the inherent instability of early-stage startups and the possibility of leaving a successful executive position only to experience a public failure. However, I concluded that my established reputation from Google would likely endure even if a venture did not succeed.

The personal risks associated with a startup CEO position were comparable to those at Google. While leading a company as a new mother would be demanding, I anticipated a reduction in extensive global travel and work across multiple time zones.

Finally, I carefully evaluated the financial implications of potential moves. Although accepting a startup salary would represent a significant financial adjustment, I determined that I could comfortably manage expenses while utilizing my savings.

Joining Polyvore

In early 2010, nearly a year after leaving Google, I identified a compelling opportunity and accepted the position of CEO at Polyvore, a fashion technology startup. Polyvore, a precursor to Pinterest, enabled users to create digital fashion and décor idea boards with directly shoppable links.

The company already had a substantial user base of young women and influencers. The founding team, led by engineer Pasha Sadri, comprised talented individuals recruited from Yahoo and Google.

Pasha was highly regarded, and we had engaged in informal discussions over the years. Polyvore had previously attempted to recruit me as CEO, both during my tenure at Google and immediately after my departure in 2008. During those conversations, I had contributed to refining their business model. I was also acquainted with Peter Fenton, a successful Silicon Valley investor who had initially introduced me to Polyvore and continued to express interest in my involvement.

Having meticulously explored my options, I felt confident in my decision. I believed that e-commerce was entering a new phase of growth, and I was eager to contribute to that evolution.

A Calculated Leap

I was convinced that Polyvore was well-positioned for success, and I was confident in my ability to contribute significantly to building a service that would resonate with millions of users. I was impressed by the strengths of Polyvore’s founder and investors and anticipated a productive collaboration.

Having addressed my concerns and negotiated my offer, I embraced the opportunity. After overseeing a multibillion-dollar profit and loss and leading a 2,000-person team at Google, I assumed the role of CEO at a 10-person fashion startup in February 2010.

As we contemplate significant career choices, we inevitably encounter critical decision points. No decision is without risk, and no framework can guarantee perfection. However, we do not require perfection or the elimination of risk; we simply need to take the next step.

By carefully considering our options, leveraging available resources, and anticipating potential challenges, we can capitalize on opportunities and navigate the inevitable obstacles that arise.

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.