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The Job-Sharing Economy With Roleshare Co-Founder and Co-CEO Sophie Smallwood

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On this episode of Redefining Work, I’m joined by Roleshare co-founder and co-CEO Sophie Smallwood. This podcast is about examining the new world of work and the leaders, like Sophie who are reshaping the how, when, what and where work happens. 

In this conversation, Sophie and I talk about the importance of mentorship, how her company Roleshare came to be, and what the job-sharing model looks like in today’s workplaces. In the effort of full disclosure, I am on the advisory board for Roleshare.

Before starting Roleshare, Sophie worked for some of the biggest names in tech, such as Meta and TripAdvisor. Sophie also worked at ‌software company Magento, which was acquired by eBay in 2011. Since then, Sophie has influenced many people’s thinking about the future of work while helping freelancers and working parents pursue their career goals.

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Ep 154: The Job-Sharing Economy With Roleshare Co-Founder and Co-CEO Sophie Smallwood Redefining Work

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The Importance of Mentorship

Sophie and I worked together at Magento — I was there for nine months and Sophie for a few years. We both connected with one of the leadership team executives, who became a mentor to both of us. 

What stuck with Sophie about this leader was that he was charismatic and passionate about his work and his team, which showed in every interaction. “When I left Magento, I stayed in touch with him. He was always helpful in trying to boost visibility of the things that I was working on and I think that kind of leadership transcends,” Sophie says.

However, this mentor wasn’t the only person from Magento who inspired Sophie. Her manager was “the textbook example of what a great leader is” and gave Sophie an unforgettable piece of advice. 

“She said, ‘You're still early in your career. And always remember, you never know where connections will come from in the future, you need to treat everybody the same,’” she says. “So you treat the CEO of a company the same way you would treat the person who is delivering the copier. Everybody's the same human. You treat them like friends.”

What Inspired Roleshare?

Sophie’s long path to co-founding Roleshare and evangelizing job sharing began early in her career during a volunteer opportunity. Sophie met a woman who was a senior marketing professional, served on a charity board and had young twins. When Sophie asked how the woman managed it all, she credited job-sharing — splitting her job duties with someone else.

This concept fascinated Sophie and got her thinking about why more companies weren’t adopting this model. So, when Sophie was looking for a change after having her first child, she saw there were few good opportunities that reflected her experience and provided stability.

“I wanted to make sure that this was something that existed. It's something that I felt that I would've used if it existed, and I decided to just make the leap,” Sophie says.

What Does Job Sharing Look Like at Work Today?

As work continues to evolve, HR and business leaders are increasingly curious about new ways of working. Importantly, job sharing isn’t just a variety of flexible working for Sophie. 

“So the way we think about it is it's a category of its own that can really support companies in helping to drive retention, as well as attracting a new category of talent who aren't looking to work full time,” Sophie says. 

Job sharing is popular among multiple demographics, including working parents, independent contractors and freelancers, and people looking to hold mid- to senior-level strategic roles without the full-time commitment. Having two people sharing the role means they’re working as a team on shared goals, and helping each other grow, too. “There's a tremendous amount of knowledge transfer and diversity of thought when people are working this way,” Sophie says.

Roleshare takes that movement and brings it together under one platform.

“Companies can leverage the Roleshare platform to match employees together to share full-time positions or match them with our own community of people who want to work this way,” Sophie explains. “In essence, retaining employees, helping to move them together and to mobilize them in a less-than-full-time capacity.”

People in This Episode

Sophie Smallwood: LinkedIn, Twitter, Roleshare