Sukhinder Singh Cassidy: Taking Risks and Catalyzing Change
How Sukhinder took a series of incremental, measured risks to become one of the most innovative leaders in Silicon Valley
Sukhinder Singh Cassidy is a leading technology executive, entrepreneur, and venture capitalist with more than 25 years of experience scaling companies like Google, Amazon, and StubHub. As the founder of theBoardlist, a company that connects exceptional female and underrepresented talent to board and executive opportunities, Sukhinder has been a force for greater gender parity and diversity in corporations across the globe. I have looked to Sukhinder as a role model for some time, so I’m very excited to share her insights.
1. Learning to Sell is Just as Important as Learning to Code
Around Stanford, the constant focus on product-led growth and highly-technical founders can leave students with the impression that engineers single-handedly built the valley. However, Sukhinder points out that this is only one part of the story: The valley was built by engineers and people who can create demand. For entrepreneurs, knowing how to generate revenue is the counterpoint to knowing how to build a product. Regardless of what you are building, dedicating resources to the revenue engine — marketing, sales, expansion, and customer success—will pay you back in spades.
During our conversation, Sukhinder recalls how some of her early roles were centered around sales; the agility and confidence she developed from having to bounce back from rejection contributed to her success as a business development executive at Google and Amazon.
2. Winners Take Multiple Shots on Goal
One of my key learnings from Sukhinder’s book Choose Possibility was the “myth of single choice,” the belief that choice is binary and either results in massive success or epic defeat. The idea that one choice will “make or break you” breeds inaction — for fear of not making the perfect next move, we stay put where we are. The truth is that winners take multiple shots on goal, and success is an iterative, incremental process. The path between risk and reward is the result of hundreds of choices, meaning that there are plenty of chances to succeed.
Sukhinder’s advice to aspiring entrepreneurs is to take small risks early and often. Some of these risks won’t materialize, but you can learn more from failure than success. Most notably, people realize that they have the ability to move forward in the face of adversity and, as a result, have a smaller fear of failure going forward.
Similarly, many college students feel pressure to figure out what they want to do with their lives, but this also should be an iterative process. There is no perfect plan when it comes to your career; rather than trying to figure out the exact industry and role you are best suited for, just choose for the next two years. Maximize your impact in those roles, and the experiences will give you the information to make your next choice.
3. Startups are a High Contact Sport
Sukhinder notes that it’s easy to fall in love with the what of a startup, but it’s much more important to pay attention to the who. Early-stage companies will almost inevitably go through a series of pivots, so it’s critical to focus on the team — their abilities, vision, values, and drive.
In particular, consider who you are going to learn from and whether he or she is what Sukhinder calls a “superboss”. These are managers who attract and retain A-players, teach you through a combination of one-on-one coaching and osmosis, and provide thoughtful, actionable feedback. They don’t have to be the nicest people in the world, but they are magnets of opportunity.
Lastly, aim for value overlap. At small companies, you can learn a lot about a culture by simply asking. As startups are characterized by a series of ups and downs, Sukhinder suggests asking how the team reacted to the most recent crisis. Not only is this a good indicator of long-term success, but it is also important to see how a manager treats employees when things get tough.
4. Leaders Reframe Problems and Take Action
While many people acknowledge that there is not enough female representation in tech, few are willing to dedicate time and energy to change that. One of the things I admire most about Sukhinder is that, despite being in an extremely demanding period of her career, she reframed an important problem and took action to solve it.
In 2016, Sukhinder challenged the prevailing belief that the lack of representation was a pipeline problem, meaning that the culture at tech startups wouldn’t change until the pipeline of women in STEM increased. She did this by creating theBoardlist, crowdsourcing a list of exceptional talent and helping CEOs identify female candidates for their boards. Today, theBoardlist is a powerful SaaS platform that allows founders, CEOs, and recruiters to tap into a diverse network of 35,000+ members for their board or C-Suite. It has been a force for positive change in Silicon Valley and beyond, and it originated from Sukhinder’s bias toward action and willingness to go beyond herself.
Sukinder’s closing piece of advice: “There are infinite permutations to the end goal. Stop stressing, take the next step, and knock it out of the park.”
To hear the entire conversation, check out the Seed Stage Stories podcast! If you have any feedback or questions about this podcast and blog, you can reach me at emcasey@stanford.edu
