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Becoming head of product in a male-dominated field

After taking a job to earn some extra cash during university, this legal software provider head of product found a passion for tech she didn’t know existed.

user iconLauren Croft 24 May 2024 Big Law
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Tobi Heskett was studying to be a history and political science teacher in the United States when she took on a job as a software trainer for extra money when she “fell in love with technology”.

Now, she works at legal software provider Dye & Durham in Australia as head of product – and has spent the last 25 years within the male-dominated technology sector learning how to identify what makes a good technology product.

“We build things to make people’s lives easier, full stop,’’ she said.


“If I can create something that makes someone’s life easier, makes their job more efficient so that they can spend more time doing whatever it is they need or want to be doing, then I’ve been a success.

“We bring customers in at the very beginning to answer questions and discover what we can do to solve problems. We ideate it, then circle back to our customers with our concepts, inviting their input to refine our ideas further.”

Having started in her role at Dye & Durham in June last year, Heskett said she was excited to continue to build on the company’s product focus.

“I’m very competitive, and it’s an opportunity for me to take this business ahead of everybody else. I’m very excited to be able to take the business on that journey,” she said.

“I was able to take my scale-up experience into an established, profitable, and secure business, and still be able to build everything from the ground up.”

In developing the product team, Heskett aimed for diversity and emphasised the importance of a “healthy debate”.

“Diversity brings people questioning the why,” she said. “Instead of everybody following like lemmings to the sea, you’ve got people coming from different angles saying, ‘Why are we doing this?’

“I don’t want five people thinking the same thing. I don’t care where you are from [or] what gender you are. If you all think the same thing, nobody is going to innovate because nobody is going to challenge the status quo.”

However, Heskett has had to navigate her career with resilience, changing the way she dressed and raising her chair in meetings to be eye level.

“When I was a consultant, I was working in higher education and worked with a lot of chancellors and deans. I would walk into a room and people would take one look at me and assume I didn’t know what I was talking about,” she said.

“So, I had to fight extra hard to prove my capabilities. I also lied about my age for almost my entire 20s. Because, for some reason, ageism plays a factor, but I was always 10 years older than I actually was.

“I took some hard slogs along the way, but it also gave me resilience.’’

Finally, Heskett said if she had some advice for her younger self, it would be “don’t take things personally” and that the only constant in the technology industry was change.

“You have to be willing to accept that change is coming and be flexible and open to it,” she said.

“I’ve watched this industry change a million times, and you have to change with it.”