The secret to landing a job as CEO of an $18b company

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Xero’s Sukhinder Singh Cassidy endured a wave of rejections when hunting for her first job after university. Her solution to cast a wider net has served her well since.

Sukhinder Singh Cassidy learnt a valuable lesson early in her career: always have multiple options on the table before making a big choice.

Before that call, the Silicon Valley-based executive had kept busy by writing a book on leadership and sitting on boards such as retailer Urban Outfitters and fintech Upstart. The entrepreneur and investor was also a manager at Amazon when it was just an online bookstore. She was Google’s president of Asia Pacific and Latin America between 2003 and 2009.Founded in New Zealand in 2006, Xero is an $18 billion software company that makes cloud-based accounting tools for small and medium-sized businesses. Sold as a subscription, its products allow bookkeepers to replace spreadsheets with a suite of digital tools to manage processes such as payroll and invoicing.

“My parents ran a medical practice in East Africa and they left late in life because of instant political instability. My dad started over in Canada when he was 49 years old and my mum was 42.”Settling in the small city of St Catharines, Ontario, Singh Cassidy was a studious child whose first experience of business was helping her father do the taxes for the family medical business when she was about seven.

“Xero is a pretty unique company. It’s at scale, growing nicely, it has macro tailwinds [the digitisation of small business], a diverse culture, large TAM [total addressable market] and the CEO job was available,” she says. The Polyvore experience wasn’t all bad. Singh Cassidy came out of it with a lesson in humility and a mantra she’s carried throughout her career: go where your values fit.

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