Women in the Workplace//

The Making of a Female CEO

These women were not “born” to be CEOs.

Courtesy of one line man/Shutterstock
Courtesy of one line man/Shutterstock

I’ve spent the past 18 months researching, interviewing, writing about and, yes, social media-stalking female CEOs for my just-published book, Girls Who Run the World: 31 CEOs Who Mean Business. In my search for the set of 31 to profile I talked to over 50 female founders and CEOs. 

Here are the 11 things that struck me most about the making of a female CEO.

1. These women were not “born” to be CEOs. They aren’t the offspring of entrepreneurs and rarely were on some deliberate trajectory with all the proper training. Most founders were flying blind and figuring their concept out along the way, knowing little to nothing about green energy/fitness/personal genetic tests before diving in. Many attended “University of YouTube” as they say, to learn flower arranging or simple coding. They are not overwhelmingly extroverts, mathletes, or prodigies. Soul Cycle co-founders Julie Rice and Elizabeth Cutler had never run a gym or taught spinning; Sara Blakely was selling fax machines when she snipped her pantyhose and invented Spanx. 

2. Passion and conviction about your idea is a prerequisite. Lisa Sugar followed pop culture obsessively growing up in Maryland. POPSUGAR started as her hobby blog for pure fun which she circulated to friends — and soon thousands and then millions were reading along. Diane Campbell of The Candy Store was selling blow pops and Hershey bars out of her locker way back in middle school. RewardStyle founder Amber Venz has been telling others what to wear since first grade, and worked in fashion even in high school. Jesse Genet who founded Lumi, a printing business, used up every birthday present acquiring screen printing supplies until she had a basement full. It was her obsession with printing processes that led her to start her company.

3. Pitch competitions provide a powerful jump-start. Maci Peterson of On Second Thought entered a South by Southwest business competition on a whim and took first prize. Her idea to enable impulsive texters to take back their screeds wasn’t even worked out, but winning propelled her to enlist an engineer and develop the technology. Emily Nunez Cavness won her first-ever pitch competition while at Middlebury College, before ever sewing a single bag from recycled military gear. This emboldened her to enter Harvard’s Pitch for Change event, which she also won. Now Sword & Plough has repurposed 30,000 pounds of military tents, uniforms, and parachutes.

4. They aren’t above any task, an ethic shaped by tedious teen jobs. In the 90s, Lisa Sugar was the best jeans-folder Urban Outfitters had ever seen. As CEO, she built her company’s first desks and still stuffs event goody bags. Growing up, Christina Stembel worked breakfast at Arby’s and the late shift at Burger King. In the early days of Farmgirl flowers, she regularly got carpal tunnel from making 80 to 100 bouquets a day. She once logged 26 miles on her Fitbit racing around helping in the warehouse.  

5. These can-do women treat no as a word, not an edict. When Jenn Hyman of Rent the Runway was headed to meet Diane Von Furstenberg in New York City, Diane’s assistant called to cancel. Jenn cunningly pretended the cell phone was cutting out. She shouted into the handset she’d be right there — then just showed up.  Beverage industry veterans told Kara Goldin that preservatives were essential for maintaining product shelf-life. She refused this notion and found a way to make her HINT flavored water preservative-free. A professor told Katrina Lake that Stitch Fix would be “an inventory nightmare.” Thirty out of 30 of her first pitches for venture funding produced no’s. But she trusted her gut and persevered. Now her business is valued over $1B.

6. They twist being underestimated into an advantage. As Rachel Haurwitz, CEO of Caribou Biosciences, says, she uses her great poker face regularly to endure slights. “I’m fine just to be the ditzy girl everybody thinks I am, and then to walk away with all their money.” This is a pervasive attitude.

7. Moxie is their superpower. Risk-taking challenges many women.But not these brazen gals.  Beatriz Acevedo of Mitu, a content provider serving the Latino market, early on told a studio executive 26 episodes of her show were ready to roll. She actually had just two. After signing the deal, she jumped to action. On the very day Melania Trump wore her green jacket emblazoned with “I Don’t Care, Do You?” to the Mexico border, Emma Mcilroy and her Wildfang gang got a mimic jacket up on their site which read “I Do Care, Don’t You?”. They sold out in hours, with all profits going to refugee relief. 

8. They stay in the game. Birchbox CEO Katia Beauchamp says, “Ninety percent of the game is staying in it.” She endured a split with her co-founder, financial turmoil, and conducting CEO business from a hospital bed while on months of bedrest with her fourth child. Anne Wojcicki’s company 23andMe basically got shut down by the FDA, all her genetic tests pulled. She worked with regulators to address concerns, and ultimately got most tests reinstated. A partnership that was going to provide Jane Chen’s business Embrace Innovations global distribution imploded at the final minute when the CEO there championing the deal got fired (she read about it in the Wall Street Journal). This forced her to ask Salesforce honcho Marc Benioff for help, someone she had met at a meditation session at the World Economic Forum. He said yes!

9. It all begins with a personal problem. After receiving multiple phone messages, Maci Peterson sent a horrifyingly embarrassing text to her ex. “Sorry I keep missing your balls…” No question why she invented an app to take back texts. Kara Goldin at HINT hated herself for drinking 10 cans of Diet Coke a day while unsuccessfully trying to shed her baby weight. Amber at RewardStyle was giving away all her advice for free. Shouldn’t she be getting paid for her fashion expertise? Jessica Matthews had her a-ha moment experiencing the lights blacking out on her aunt’s Nigerian wedding, and the nasty polluting generators coming out. Before long she had a solution to produce power from kinetic energy produced by kicking a ball.

10. They have mastered the art of the cold call and cold email. This skill may seem basic but its critical — and tricky. How did Katia Beauchamp sign Benefit Cosmetics as her first partner to provide samples for her initial subscription boxes? She honed her subject lines into click-bait. In the email itself, she made tiny asks that were hard to refuse like could you spend five minutes on the phone with me answering one or two questions? The made sure her messages were short, so the reader never had to scroll beyond a single screen. Spanx CEO Sara Blakely called Neiman Marcus, asked for the hosiery buyer, and finagled a 10-minute meeting. Soon, they were stocking her product.

11. They act like women. These CEOs cry at work. They bring nursing babies to the office. They fill their ranks with women. They excel at communicating and prioritize company culture.

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