Squishy conversations? Retain staff and challenge the status quo with Carla Caldwell
Carla Caldwell didn’t follow the same path as the rest of her family. Medicine just didn’t appeal to her. But accounting and education did.
Summary
Working while putting herself through college was her first exposure to accounting and business administration. The company she worked for went through a software implementation that went unexpectedly poorly, but it led to an epiphany.
“I realized all of my accounting knowledge and my nerdy techie knowledge could combine together as a big superpower,” she says.
Her passion for tech education and accounting led her to education roles at Sage and Xero. But in 2015, she struck out on her own with Caldwell Consulting and Training. There, she helps accounting firms with tech implementations, process improvements, and education.
Carla also operates Candella Accounting & Advisory Services, a group of nine women who do accounting and bookkeeping for nonprofits and small businesses.
Carla joins her old friend and Karbon co-founder Stuart McLeod on episode 68 of the Accounting Leaders Podcast, where they reminisce on the pre-Karbon days and talk about tech innovation. Plus, Carla shares why accounting leaders should be asking “squishy questions”.
Battling the status quo
At Xero, Carla worked on the leading edge of converting accounting to the cloud.
And in the early days of cloud accounting, it was more than just one company vs. another. It was a non-growth mindset and resistance to change that brought the biggest battles.
“It was exciting to explore something new and talk about different ways of doing things,” she says. “I will never forget having a sign-on sheet on an iPad for people to use to check in for their CPE. It was a PDF on an iPad—it was the coolest thing. And it was so different and we said ‘Okay, we’re embracing this technology and we’re really going to do things differently and think differently’. It was exciting to be in the early stages of that.”
Not only was she at the forefront of the cloud accounting revolution, she was also a pioneer of remote work in the US. After she had her son, she petitioned Xero to let her work from home like her colleagues in New Zealand.

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