The Strategist: Rebekah Stephens

As the business development manager with Common Wealth Development for nearly three years, Rebekah Stephens used her own experiences and strategic skillset to uplift startup business owners.
Rebekah Stephens

Rebekah Stephens is the kind of person who sees the silver lining in everything. Photo by Paulius Musteikis

There is so much that could have broken Rebekah Stephens’ spirit. At 33, she lost her job, was evicted from her apartment and had her car repossessed all within a few months. But Stephens is the kind of person who sees the silver lining in everything. “In people, in jobs, in situations, even the thing that sucks the most, there’s always something — some type of glimmer of hope and happiness,” says Stephens.

She was dealt another series of blows in 2019 when she experienced a season of loss. She held an ill friend’s hand as the woman took her last breath in hospice. Then her father died after multiple health issues, as did the woman who was like an aunt to her. Then she lost her best friend to suicide. “It left me really numb,” she says.

To cope, Stephens clung to small bits of joy and leaned into her instinct to help others. As the business development manager with Common Wealth Development for nearly three years, Stephens used her own experiences and strategic skillset to uplift startup business owners. Her role entailed overseeing the day-to-day operations and well-being of Madison’s two oldest incubators, The Madison Enterprise Center and Main Street Industries. At any one time, these incubators house about 30 small businesses at accessible downtown locations with office space, and Stephens helps the entrepreneurs with whatever they need, pointing them in the right direction to secure loans, apply for grants, find accountants or just talk through business strategies.

“She’s so excellent at identifying the things that people don’t necessarily see,” says Megan Diaz-Ricks, the director of economic development at Common Wealth. “So when we’re having conversations about, ‘How do we pivot?’ or, ‘How do we make our programs better?’ she’s always constantly identifying things that we may not have thought of.”

Diaz-Ricks says that during the pandemic, Stephens had the incredible idea to connect the tenants of Common Wealth’s 140 affordable housing units for low- to middle-income households with business-starting resources. “For a lot of those folks, they didn’t really think that small business ownership was in their reach,” Diaz-Ricks says. But Diaz-Ricks has seen it done often — it’s just a matter of making the connections, like those that Stephens facilitates. “Rebekah has been a ‘low-key’ force in the incubation world,” Diaz-Ricks says, adding that she’s been an advocate for more resources, education and funding opportunities for women- and BIPOC-owned businesses in particular.

Stephens has since been competitively recruited to become a talent supply chain consultant at Kelly Services, where she’ll help secure talent for an agriscience company. Her ability to see more than what might appear on a resume means that in her new role, she’ll still be able to support people who might be traditionally overlooked. “There’s so much talent in women and in people of color and underrepresented populations,” she says. “It’s there, but sometimes they don’t necessarily have all the tools that they need, be it opportunity, be it education, whatever it is. They may not have that strong business background on paper, but they know what they’re doing. They have to get their foot in the door somewhere to be able to make it happen.”

This is the kind of strategic thinking reminiscent of Amy Gannon’s work. Stephens met and came to know Gannon through the Social Good Accelerator, a program that works with BIPOC and women-led business founders who want to make a social impact. Stephens has two business concepts of her own that she’s currently developing, both in honor of her best friend who died by suicide — one is a children’s book about sharing and navigating emotions, especially for children of color; the other is a website and live events that will help people find for the first time or rediscover joy.

“Rebekah is an emerging and shining star in the start-up/entrepreneurial world,” Diaz-Ricks says.

Read more about The Amys here.

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