The Lavin Agency Speakers Bureau
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Sukhinder Singh Cassidy
In a volatile world, our biggest opportunity lies in revolutionizing our relationship with risk.
Founder of theBoardlist | Former president of StubHub | CEO OF XERO | Author of Choose Possibility
Sukhinder Singh Cassidy is one of the most well-respected female tech executives in Silicon Valley. Named one of Fast Company’s Most Creative People in Business, she’s the CEO of software company Xero and former president of StubHub. She’s helped scale companies like Google and Amazon, and founded theBoardlist: a premium talent marketplace for leaders. But despite her many successes, she’s the first to admit her path hasn’t always been linear. In her bestselling book Choose Possibility, Sukhinder reveals the many poor choices, misfires, and unexpected headwinds she’s encountered along her path—providing a thoughtful new perspective on risk-taking: what it is, what it isn’t, and how to master it to achieve lasting success.
“Sukhinder is one of Google and Silicon Valley’s most successful and well-respected leaders. In Choose Possibility, she brings her unique style of authenticity, optimism, and hustle to help anyone unlock their career potential.”— Eric Schmidt, Former Chairman & CEO, Google
Sukhinder Singh Cassidy is the CEO of Xero, a leading publicly listed provider of cloud accounting software to small businesses and their advisors in over 180 countries globally. She is also an experienced CEO, global leader, entrepreneur and board member with more than 25 years’ experience building and scaling global companies including Google, Amazon, Yodlee, Stubhub and Joyus.
Sukhinder joined Xero in November 2022, and is responsible for the company’s multi-channel, multi-product, global business. Under her leadership over the last 2 years, the company has transformed its global leadership team and operations, achieved Rule of 40 profitability alongside high growth, and more than doubled in value to $27bnAUD. In that time it has also outperformed both the EMCloud Index of the best performing cloud companies globally, and the AXS Index, becoming a top 20 company on the exchange.
From 2018-2020, Sukhinder served as the President of StubHub Inc (a subsidiary of eBay), a leading global ticketing marketplace for live entertainment with US$5B in GMV, and over US$1B in global revenues. Sukhinder was responsible for Stubhub’s global business and also served as a member of eBay’s global executive leadership team. In 2020, Sukhinder and her team successfully helped lead and execute the sale of StubHub to Viagogo for $4bn, and then the immediate COVID crisis response thereafter.
Prior to Stubhub, Sukhinder was the founder, Chair and CEO of Joyus from 2011-2017, an early video commerce pioneer, where she grew revenues from 0-$20m, built patented video commerce technology, and distributed shoppable video across the web’s leading publishing sites. From 2003-2009, Sukhinder was President, Asia Pacific & Latin America at Google, where she successfully built its operations from less than US$100 million in revenue into a multi-billion dollar business, spanning 103 countries.
Prior to Google, Sukhinder co-founded fintech pioneer Yodlee in 1999 and served as SVP of Sales and Business Development during its first 5 years, where she established its business model and leading market share as a data aggregator to the US financial services industry. A Canadian native and graduate of the Ivey School of Business Administration at the Univeristy of Western Ontario, Sukhinder started her career in investment banking with Merrill Lynch in New York and London. Sukhinder currently serves as lead independent director of AI lending platform Upstart (UPST), and has previously served on leading tech, consumer and retail boards including Ericsson, TripAdvisor, Urban Outfitters, Stitchfix, and J. Crew.
She is also the author of the Wall Street Journal bestseller, Choose Possibility, which offers advice on how manage and optimise risk-taking for professional growth, and founder of theBoardList, an online talent marketplace connecting CEOs with over 40,000 qualified diverse board candidates, which merged with BoardProspects in 2023.
For her work in the tech industry, Sukhinder has been profiled in numerous publications globally, including Fortune, Forbes, Wall Street Journal, Business Week, The New York Times, Bloomberg, Vanity Fair, Vogue, Techcrunch, AllthingsD, Ad Age, CNBC, the AFR, and several leadership books, including: The Money Hackers, How Good Leaders Learn, Innovation Nation and Geek Girl Rising.
Speech Topics
Change ManagementRead more
Choose PossibilityTake Risks and Thrive (Even When You Fail)
The pandemic may have made many of us more risk-averse, but ironically, it’s also taught us an essential lesson about the role risk plays in our lives: whether we embrace it or shy away from it, in an increasingly volatile world, we will continue to encounter risk everywhere. Our biggest opportunity is to become agile and adept at taking risks to grow—treating it like a repeatable process we can practice, not a one-off event.
Sukhinder Singh Cassidy is no stranger to risk. One of the most well-respected female tech executives in Silicon Valley, she has taken hundreds of personal and professional risks throughout her career. And what she’s come to realize is that success does not come from making one singular “correct” or “big” decision; rather, it comes from tackling a series of small choices, aimed at optimizing future possibilities.
What the world needs is a new paradigm, says Sukhinder. A risk-taking framework that can help each of us have a healthy, proactive, and ongoing relationship with risk in order to unlock our own impact. In this fascinating presentation, she shows us how we can build that paradigm, using deeply personal stories alongside a simple set of frameworks anyone can understand. Audiences from every walk of life will leave this talk inspired to rethink their relationship with risk and find new growth: whether it’s managing change, reimagining work, or taking their careers to the next level.
InclusionRead more
Building a Culture of Belonging Starts With Leadership
As the highest decision-making body in an organization, a board must reflect the values of its company. But having a range of perspectives in leadership isn’t enough. An inclusive culture that supports each member’s unique lived experiences, celebrates their difference, and ensures everyone is equally heard is critical—both for galvanizing support for inclusion and belonging initiatives, and for creating a healthy, equitable workplace in general.
Sukhinder Singh Cassidy knows first-hand the challenges of working in largely white, male-dominated spaces. A first-generation Indian immigrant, she navigated her way to becoming one of the most highly regarded women in tech—working for companies like Google, Amazon, and StubHub over the course of her 25-year-career. Today, she’s the founder and chair of theBoardlist: an organization connecting exceptional talent from a range of backgrounds with global board opportunities. “Our ultimate goal is to help companies create full and true representation in their leadership, so that they can better serve their customers, employees, and communities,” says Sukhinder. This talk is an extension of that mission—debunking the myth of the “pipeline problem” to help companies build more equitable boards, leadership, and cultures.
Filled with exciting and personal stories gleaned from years of on-the-ground experience, this talk reveals how Sukhinder has built companies, scaled businesses, and thrived as a leader—and how you can apply these strategies to your own organization, deepening your brand’s impact from the inside out.
LeadershipRead more
Diary of a CEOSecrets to Scaling Yourself and Your Teams
There is a notion of the journey from founder to CEO. But on-the-ground, this journey rarely pans out in a linear fashion, says Sukhinder Singh Cassidy: a leader with over 25 years of experience founding, scaling, and advising companies like Google, Amazon, and StubHub. What she’s discovered along the way is the conventional leadership wisdom we so often hear doesn’t necessarily serve executives hoping to take themselves, their teams, and their organizations to the next level.
In this powerful presentation, Sukhinder debunks overly simplistic business advice with no grasp on reality. In its place, she offers an actionable roadmap for how to become truly multifaceted leaders who can attune to their companies’ needs—even if that means venturing outside their comfort zone.
With credentials running and scaling teams from day one—running multi-billion dollar, global organizations with thousands of employees—Sukhinder has unique insight to what makes a great leader. She offers her wealth of experience in a way that is fresh, engaging, and most of all, motivating for anyone hoping to maximize their growth.
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