We Are Rosie’s CEO Stephanie Nadi Olson Creates Flexible Work for Women

we are rosie

Stephanie Nadi Olson, founder and CEO of We Are Rosie, joined Cheddar to discuss her commitment to diversity in the workplace as part of our Women Who Roar series. Read on to learn about the opportunities her organization is creating, how the pandemic is affecting women in the workplace, and why financial literacy is a critically important part of independent work.

We Are Rosie provides access, opportunity, and wealth to independent marketers  

We Are Rosie is a thriving community of independent marketing experts, available on-demand to augment, complement, backfill, or accelerate in-house teams and capabilities. Stephanie started the company in 2018 to support extraordinary people while providing a workplace that treats everyone with dignity and gives access to opportunities for growth. 

A marketing technology veteran, Stephanie recognized foundational issues in traditional work structures — nine to five schedules, mandatory in-office settings, and an insistence that workers live in major markets. She realized these expectations countered diversity and inclusion goals. 

Determined to facilitate positive change, Stephanie built We Are Rosie to create a home for people longing to work in a more flexible way while helping them attain the careers they desire. Over the past three years, We Are Rosie has built a network of over 7,000 freelancers, and the organization maintains a strong commitment to inclusion. 

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Stephanie’s diverse upbringing inspired her to create opportunities for marginalized workers 

The daughter of a refugee and raised in a mixed-race and mixed-religion household, Stephanie grew up with an appreciation for different backgrounds. Her childhood helped her recognize “the magic that can happen when we allow people to come together in a diverse way.”

Stephanie fostered this magic as she moved forward in her career and made it her mission to create opportunities for people who are “traditionally left out of the room when opportunities and wealth are being handed out.” Now that world is in a COVID recession, millions of people are being forced to leave the room, and she’s determined to help.

The pandemic set back women’s progress in the workforce, but there is a silver lining

The COVID-19 pandemic has driven 2.5 million women out of the workforce, amplifying pre-existing gender gaps. They are being disproportionately impacted with furloughs and layoffs, and many mothers are quitting jobs to care for children. 

This has certainly set equal rights movements back, but Stephanie sees a silver lining. She said, “We are at a moment in history where we are being forced to reconsider the way work happens. We are being asked to reconsider a lot of the notions we accepted as mandatory, in terms of how people have to show up at work. I think if we use this collectively as a time to rebuild a much more inclusive and flexible system of work, we’ll be able to retract and retain not just women but all the people who have been marginalized out of the rigid way work happened.” 

Creating a more inclusive and flexible workplace is half the battle. Independent workers also need financial literacy in order to thrive.

Financial literacy is critically important to independent workers

Many of the people in the We Are Rosie community came from traditional nine to five workplaces. Stephanie often hears about how jarring it is for first-time independent workers to embrace the idea that they are now business owners (whether it’s one person working freelance or a small team that started an LLC). 

She said, “All of the sudden you have significant responsibility for your own finances, even things as basic as putting money aside to pay taxes in a proactive way as a business owner. So, financial independence, literacy, and empowerment are critical components to the success of independent talent and to continue working in a way that makes sense for their lives.”

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