Xero CEO Sukhinder Singh Cassidy has founded three businesses and formerly led Google's Asia-Pacific operations. Photo / Getty Images
Xero CEO Sukhinder Singh Cassidy has founded three businesses and formerly led Google's Asia-Pacific operations. Photo / Getty Images
Sukhinder Singh Cassidy has many identities; she’s a Canadian Sikh, mother, best-selling author, entrepreneur, investor and Xero’s third chief executive.
Whichever roles she’s juggling in whichever time zone she’s in, she says there’s always one emotion she’s feeling — guilt.
“Mostly, I just spend my time feeling guilty that I’mnot at home to feed my son pancakes, or if I’m home feeding him pancakes, somebody can’t do a call with me when they need me,” she told the Herald this week.
“You just get used to feeling guilty all the time.”
For such a high achiever, Singh Cassidy is quite open about failure and feeling like one. She even wrote a book about it — now a Wall Street Journal bestseller.
“For you to have success, in fact, inevitably there’s failure in it.”
Reflecting on her own, she recalled her first chief executive role, which lasted six months.
In 2009, she left Google as its president of Asia-Pacific operations to lead a fashion startup. But when she and the founder had different visions for the company, the board did not side with her.
“I thought it would sink me. I thought no one will ever hire me again.”
Obviously, that fear didn’t come to fruition.
Sukhinder Singh Cassidy was named Xero's new chief executive in 2022. Photo / Xero
The San Francisco-based executive began leading one of the world’s fastest-growing software companies in November.
Xero has 3.74 million subscribers in 180 countries using its accounting software, totalling almost $1.4 billion in annual revenue. It has staff in New Zealand, Australia, the United Kingdom, the United States, Canada, Singapore, Hong Kong and South Africa.
At the company’s annual result in May, Singh Cassidy announced a $34.7 million restructure to reduce headcount by 15 per cent, affecting up to 800 roles, and $126.4m of write-downs on two businesses.
It blew out the company’s annual loss to $113.5m, from a previous loss of $9.1m.
At the time Singh Cassidy phrased the decision as short-term pain for long-term financial gain.
“This gives us greater ability to deliver better value for all stakeholders and take advantage of the significant opportunity ahead,” she said in May.
Xero is an accounting software service founded in Wellington.
This week, she acknowledged those decisions were difficult to make.
“We made some hard choices early to really get ready for that future, I would say, in a more nimble and effective way.”
Xero’s future was focused on convincing 45 million small business owners globally to use its software to manage their finances and payroll.
Singh Cassidy said that’s the “opportunity” that attracted her to the role.
It also ticked many boxes for her; scale, macro tailwinds, attractive unit economics, healthy gross margins, a customer she loved to serve and a culture of diversity and inclusion.
“It’s that unique combination.”
Not to mention, she understood its customers deeply because she was one.
Her company theBoardlist — a talent listing platform to promote women and underrepresented minorities on company boards — started using Xero eight years ago, after being introduced to the service by its accounting firm in Denver, Colorado.
“We manage our small amount of cash very tightly ... and Xero is a pretty essential part of that journey for us.”
TheBoardlist is one of three businesses Singh Cassidy has started and exited.
She co-founded Yodlee, a financial data aggregating platform, almost 20 years ago, and Joyus, a video shopping channel, which she later sold to an e-commerce company.
“I think what I wear proudly as a badge of honour is I have lived the life of a founder and entrepreneur.
“So I feel very personally the journey of our customers.”
But, being a chief executive is a job she says she wouldn’t trade for any other in the world.
As a woman of East Indian heritage, she knows she’s a minority to take that seat.
“I hope that as a leader I walk the walk,” she said.
“I just believe that diverse perspectives build better outcomes. I mean, period.”
So, how would she measure the success of Xero’s outcomes under her leadership?
Her predecessor, Steve Vamos, who led Xero for five years, grew its subscriber base from 1.4 million to 3.5 million, with annualised monthly recurring revenue tripling to $1.5 billion.
Former Xero chief executives Steve Vamos and Rod Drury, who founded the company. Photo / NZME
Singh Cassidy says she can’t pick one measure, nor should she because she’s ultimately responsible for it all.
“Think of it as the whole enchilada. Your job is to balance and optimise the whole, and hope you’re doing a good job for your employees and all your stakeholders at the same time.
“I’ll feel like I’ve done my job if ... we become an even higher-performing global SAAS (software as a service) company.”
Her own advice to those navigating their careers: “Just stay focused on having impact, and somehow, in hindsight, it all works out.”
