Entrepreneurs / Finance / Women in tech

‘Knowing your numbers can change your life’: How this entrepreneur is redefining the role of CFO

Denai Wolfe, founder of The Chic CFO, offers high-level financial strategy services to businesses that otherwise can't afford to hire a chief financial officer.

Denai Wolfe. (Courtesy photo)

Two years ago, Denai Wolfe was working 50 to 60 hours a week as a chief financial officer for a large company, and five months pregnant with her second child.

“I really didn’t want to do it anymore,” said Wolfe, in an interview with “I decided I needed to to start my own company.”

She had the skills to do freelance bookkeeping from home, but while listening to financial podcasts during a beach vacation, she discovered the existence of the virtual CFO. An alternative to a traditional CFO — a full-time executive with an executive salary — a virtual CFO offers the same high-level financial strategy services to businesses that otherwise can’t afford it.

“It’s a new concept, this idea of a virtual CFO,” she said. “A lot of people have accountants, a lot of people have bookkeepers, but your average small business owner doesn’t really have a financial coach. They don’t have somebody looking at their finances and talking to them on a weekly basis. Being a bookkeeper is number crunching. I want to strategize with them and talk about what these numbers actually mean.”

She started small, with one or two clients as a side hustle. By her ninth month of pregnancy, she quit her job, confident that the business would allow her to make enough money working from home.

After taking a couple of months off, she got the business, The Chic CFO, going in earnest.

“Initially, I really thought it would stay a side thing,” she said. “We planned to have a nanny come in one day a week so I could work.”

Today, 18 months later, the nanny is on hand five days a week, and she’s just hired three new employees to handle a growing number of clients. She still works 100% from home.

Now, Wolfe is continuing to reach out to other women entrepreneurs — not least of all professional women looking to change the landscape of their careers as they enter motherhood and other stages of their lives.

Entrepreneurship is not new for Wolfe.

“I always had this entrepreneurial spirit,” she said. “I had started a photography business, then I opened two restaurants, all while working full-time.” She launched the restaurants — two Primo Hoagies locations, one in Wilmington and the one in Bear — in 2012. At 24 years old, that made her the youngest 100% owner of a brick and mortar in Delaware at the time.

“To make a long story short, after the first year I was so broke I had to [refinance] my loan,” she said. “And I was like, ‘I’m working seven days a week, why am I broke?’ And I realized it was because I wasn’t in touch with the numbers.”

It was a realization that would alter her entire trajectory.

“That was how I started the journey of diving into accounting and learning what you could do to turn a business around,” she said. “I went to my boss and said I wanted to move from operations to the finance team, because that’s what I was passionate about, and in three years, I paid off $160,000 worth of loans for the Primo Hoagies.”

That success inspired Wolfe to spread the word to other entrepreneurs. “I started volunteering at the Women’s Business Center to talk to female entrepreneurs about the empowerment that comes with knowing your numbers, and how you can change your life and change your company,” she said.

Through those classes, Wolfe met Kelly Jones, founder of The Cleaning Girl, Inc., and the 2018 Delaware Small Business Association’s Woman Owned Business of the Year. “Kelly was one of the first ones to sign up” as a Chic CFO client.

Jones also encouraged Wolfe to start a LinkedIn profile, which would turn out to help with her other businesses.

“When my younger son was one week old, I got a message on LinkedIn at midnight,” she said. “A guy had reached out saying, ‘I see you have two Primos, I’m buying locations, I want to talk to you about your store.’ So I call my corporate office the next day [to confirm it was legit]. So a couple of days later, my husband and I meet with him at Iron Hill Brewery, we visit both of the stores, and by the time we pull back into our driveway, we an all-cash offer, 30-day close for him to buy those stores.

“I’d had no plans to sell, but it was a very aggressive offer,” she said. “Later he said to us, ‘I had met with so many stores, and none of them showed up to the meeting with financial reports and knew their numbers the way you do, and that told me that you had a well-run store. And that’s why I moved so fast.’ And I looked at that as another example of how knowing your numbers can change your life.”

As The Chic CFO’s business is booming, with nearly two dozen clients around the country, Wolfe is continuing to reach out to other women entrepreneurs — not least of all professional women looking to change the landscape of their careers as they enter motherhood and other stages of their lives.

“I’m in the process of creating an online course for other women like myself who come from working full time, doing that grind serving customers in their finance department, and saying, ‘Listen, you can do this on your own,’ Wolfe said. “I’m in the process of working on that.”

In the meantime, you can catch Wolfe’s new weekly podcast, “The Profit Factor,” on standard podcast services.

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