Xero CEO Sukhinder Singh Cassidy on having a founder's mentality and her biggest career regret

How do you get ahead as a finance professional when you work for a large company?

In this week's edition of the Finance Wrap-Up newsletter, we chat to Xero CEO Sukhinder Singh Cassidy about having a founder's mentality, her biggest career regret and the top qualities she looks for when hiring staff. Earlier this year, the accounting software company revealed it hit the 'Rule of 40' milestone — a combined revenue growth rate and profit margin that is used to judge the success of a software as a service (SaaS) company.

Sukhinder, you’re an entrepreneur who founded three companies before joining Xero. How do you bring a founder's mentality to your career when you’re working for a large company?

The first thing I always say is to treat anything like your own. So having been a founder where literally the company's fate does rest or die on your decision, you have both an appreciation for how hard it is to start something, but also the carry you need to put into it.

So I think the way you bring a founder's mentality to anything you do is put a level of care into anything like it's your own. And in a large company, that looks like people who don't quit, go the extra mile, or log in at 11pm at night to send you something. And those extra inches — they add up.

Xero CEO Sukhinder Singh Cassidy uses 'pipelining in parallel' to make better decisions. Watch the video below.

What’s your biggest career regret — and what can others learn from it?

I started companies that were often too early for their time. My second company [JOYUS] is maybe one of my bigger regrets. It was an early video commerce platform online.

Now, today the idea of shopping on Instagram or TikTok is pretty well known. But I started that company in 2010 and I drove it to about US$20 million in annual revenues and then I couldn't find anyone to fund it. And I gave up and we sold it for a very small sum. And sometimes I have a regret that I just didn't ride it out, that I didn't persevere long enough because it turns out that video shopping came a couple of years later. So I was right, I was just early.

When hiring people, what qualities and skills do you look for?

I think the number one skill people need is adaptability. I think people are looking for those who can flex and adapt to different circumstances and situations because almost every category, industry, job is changing right now.

Number two, you want people to have that owner's mindset — people who, when you call and ask for their reference check, what you'll hear back is, "This person cares deeply. They go the extra mile. They do the things that others are unwilling to do, even if it's grunt work." Flexibility and owner's mindset — that is a killer combination.

What qualities do finance professionals need in their career? Share your thoughts in the comments.

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