#244 Sukhinder Singh Cassidy: Xero's CEO on Intensity as Superpower + Kryptonite, Father’s Influence & Xero's 3×3 strategy in the AI era episode artwork

EPISODE · Feb 17, 2026 · 1H 3M

#244 Sukhinder Singh Cassidy: Xero's CEO on Intensity as Superpower + Kryptonite, Father’s Influence & Xero's 3×3 strategy in the AI era

from The High Flyers Podcast with Vidit Agarwal · host Vidit Agarwal

Episode #244 features Sukhinder Singh Cassidy, CEO of Xero — the publicly listed small business platform serving ~4.6 million subscribers across 180+ countries.In conversation with Vidit Agarwal, Sukhinder reflects on her journey from growing up in a deeply values-driven Sikh household in Canada to leading global teams at Amazon and Google, founding three companies, and now steering Xero through its focused 3×3 strategy, US expansion, and AI transformation.She speaks with rare candour about intensity as both her superpower and her kryptonite, taking time off before every job and how lessons from banking, Google and her founder missteps now shape her leadership at Xero. Sukhinder also unpacks Xero’s focused 3×3 strategy, the secret to unlocking further growth in the US, Building product in the AI era, filtering customer insights and more.Please enjoy exploring your curiosity!________To support this podcast, check out our some of our sponsors & get discounts:→ $1,000 off Vanta: Your compliance superpower — vanta.com/high→ Find out more about the Law Firm Allens and how they can help your company today at www.allens.com.auIf you're keen to discuss sponsorship and partnering with us or recommend future guests, email us at [email protected] today!Join our stable of commercial partners including the Australian Government, Google, KPMG, Vanta, Allens, Notion and more.________Show notes and more episodes hereFollow us on Instagram, LinkedIn or TwitterGet in touch with our Founder and Host, Vidit Agarwal directly hereContact us via our website________The High Flyers Podcast features in-depth interviews with the world’s most influential figures in business, tech, finance, government and sport. Launched in 2020, it has ranked in the global top ten for past three years, with listeners in 27 countries and over 200+ episodes released, and featured in Forbes, Daily Telegraph, and at SXSW.Our guests include -- Malcolm Turnbull (Prime Minister of Australia), Anil Sabharwal (Global VP, Product at Google), Jason Collins (Head of BlackRock, Asia Pacific), Stevie Case (Chief Revenue Officer, Vanta), Brad Banducci (CEO, Woolworths), Jean-Michel Lemieux (CTO, Shopify + Atlassian), Sweta Mehra (EGM, NAB; ex CMO, ANZ), Bowen Pan (Creator, Facebook Marketplace), Sam Sicilia (Chief Investment Officer, Hostplus), Craig Tiley (CEO, Tennis Australia), John Haddock (CBO, Harvey), Niki Scevak (Co-Founder, Blackbird Ventures), Mike Schneider (CEO, Bunnings), Trent Cotchin (3x Premiership Winning Captain, Richmond FC), Peter Varghese (Secretary of Foreign Affairs, Australian Government), Jack Zhang (CEO, Airwallex), Matteo Franceschetti (CEO, Eight Sleep) and more.

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Episode #244 features Sukhinder Singh Cassidy, CEO of Xero — the publicly listed small business platform serving ~4.6 million subscribers across 180+ countries. In conversation with Vidit Agarwal, Sukhinder reflects on her journey from growing up in a deeply values-driven Sikh household in Canada to leading global teams at Amazon and Google, founding three companies, and now steering Xero through its focused 3×3 strategy, US expansion, and AI transformation. She speaks with rare candour about intensity as both her superpower and her kryptonite, taking time off before every job and how lessons from banking, Google and her founder missteps now shape her leadership at Xero. Sukhinder also unpacks Xero’s focused 3×3 strategy, the secret to unlocking further growth in the US, Building product in the AI era, filtering customer insights and more. Please enjoy exploring your curiosity! ________ To support this podcast, check out our some of our sponsors & get discounts: → $1,000 off Vanta: Your compliance superpower — vanta.com/high If you're keen to discuss sponsorship and partnering with us or recommend future guests, email us at [email protected] today! Join our stable of commercial partners including the Australian Government, Google, KPMG, Vanta, Allens, and more.

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#244 Sukhinder Singh Cassidy: Xero's CEO on Intensity as Superpower + Kryptonite, Father’s Influence & Xero's 3×3 strategy in the AI era

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This episode was published on February 17, 2026.

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