Why Rajini Carpenter made the leap from corporate finance to VP of Engineering at Deputy

Bronte McHenry
October 22, 2021
Deputy VP of Engineering Rajini Carpenter
Deputy's VP of Engineering Rajini Carpenter

Rajini Carpenter moved from corporate finance to workforce management startup Deputy because she wanted to experience the rollercoaster that is startup growth.

“I've been in financial services for 20 years. It’s been a long time working for banks and big corporates,” Rajini tells me.

“I've experienced how big organisations work, listed on the stock exchange and whatnot. I know how to navigate and get things done in a big organisation with red tape.

“The reason I took the role at Deputy is I’ve never experienced a company going from startup to IPO. The thing about startups is that they never stay startups. I wanted to experience that.”

But while she joined the team ready for an exciting ride, the reality of startup life has been better than she imagined. 

In addition to experiencing rapid growth firsthand, she has taken to doing customer discovery interviews on the fly, flourished as a “people engineer” and found her feet as a leader. This is her story. 

A feedback loop-the-loop

Rajini was immediately excited about Deputy’s value proposition, but it is the connection she now has to their diverse and everyday customers “Shift workers” that gets her out of bed in the morning.

“Deputy’s product-market fit is absolutely spot on in terms of helping end-users as well as the managers,” Rajini says. 

“Before lockdown, I saw my physio, and she told me she uses Deputy. Of course, I asked her what we can do better and she said: ‘I often forget to clock out because my phone's always in my bag and my job is always in and out’.”

This was an insight Rajini took back to her team, who then pushed an update that enables users to clock-in/clock-out on their Apple Watch easily.

“When I go to cafes or meet people randomly, I ask them for feedback. That’s how engaged the end-users are,” Rajini tells me.

“It’s really incredible to hear from the customer, how they are using the product and how it's helping their lives.”

Becoming a “people engineer”

When Rajini was employed as an engineer, she was very shy, never used to talk with colleagues, and spent the majority of her time working with her headphones on.

“I was relatively isolated as a result of my introverted nature,” she admits.

“But being in a leadership role demands you to talk to people and listen to them. 

“As a CTO or Senior VP, you can't just sit in your box and keep doing the technology thing. You also need to be a people engineer. After all, how people work together is how you achieve greatness.”

These days, Rajini approaches leadership in the same way she approaches engineering. 

“If you think about engineering and how you bring different components together and make it work, the same principles apply to people and how they collaborate,” she tells me.

“Nowadays, people come from different skill levels, age groups and backgrounds. Enabling people to work well together, it's a skill and an art in itself.

“It's a journey that most people who are aspiring to be leaders have to go through.

“In my experience, individually understanding what makes people tick is very important to creating high-performing teams. I enjoy that most about my job.”

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