Nothing Artificial About Her Leadership: Tech CEO on Leading With Empathy
Perhaps the writing was on the wall from the time she was a teen.
At 16, Heather H. Wilson was a national officer for Future Business Leaders of America as a student at James Wood High School in Winchester, Virginia, where her mother was a teacher. Her father was an art teacher at an elementary school in town.
“I was raised by two educators who set very high barress and standards,” says Wilson, CEO of CLARA Analytics, the leading provider of artificial intelligence technology in the commercial insurance industry.
“Going to the high school where my mother taught, I was always on my best behavior,” says Wilson, who also played on basketball and volleyball teams and participated in gymnastics as well as music.
Her best was enough to put her on a trajectory for C-suites in some of the largest corporations and entities in the world.
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A faith-based, well-rounded upbringing “taught me about cause and effect and consequences. I learned you can have a great IQ, but if you don’t have a great work ethic, and a heart of service, it’s not going to come back to you,” says Wilson, who joined CLARA (named after its location in Santa Clara, Calif.), in June 2021.
Graduating high school in 1989 with a class of 650 students, Wilson went to local Shenandoah University, “because I wanted to craft my own curriculum and I wanted to be multilingual,” says Wilson, who also serves on Equifax’s Board of Directors on the Audit Committee and Technology Committee.
As the first Rotary Club Scholar from her area, Wilson studied in Tokyo, was introduced to the then mayor of Moscow, and arranged to study at the University of Moscow. Fluent in both Japanese and Russian, she graduated college in 1993, after four and half years, which she says disappointed her parents because of the extra semester.
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That year she and a fellow Russian student started an import company for U.S. businesses shipping consumer products from Russia and Japan. While she had other job offers, Wilson says, “I wanted to do something I had never done and where there were not a lot of women.”
It turns out there were not a lot of women in any of the industries where she has worked in her career. Joining Andersen Consulting in 1994, Wilson was later appointed to the U.S. Treasury Financial Research Advisory Committee in Washington, D.C., where she stayed for six years.
“It was an ‘aha’ moment, there were not very many women there. I loved figuring out what the problem was and how to solve the problem,” she says.
Working in data and analytics next at Deloitte, Wilson then worked at Kaiser Permanente 2007 to 2010 as Global Head of Innovation and Advanced Technology, responsible for overseeing the strategies and implementation of leading-edge, data-driven analytical programs. She also launched the Kaiser Permanente Women in Technology group, focusing on mentorship and retention for women in math, technology and science.
“I came in and developed algorithms to see how someone would get health concerns like diabetes or hypertension. We started to think about prevention when you looked at people’s health. We worked on medication adherence in innovative ways,” says Wilson. And she was key in the creation of the Kaiser Permanente Center For Total Health that opened in Washington, D.C. in 2011.
From there, Wilson was Chief Data Officer at Citigroup and Global Head of Decision Management, responsible for spearheading new analytical capabilities companywide from 2010 until 2011. It is also where she was an Executive Member of Citi4Women at Citigroup, leading predictive analytics around retention.
Joining AIG as Chief Data Officer in 2012, Wilson says, “They had great vision around data and what to do with data for claims, and how to make it customer centric.”
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At AIG where she worked until 2016, she launched Global Women in Technology and served as Executive Sponsor of Girls Who Code.
After her twin sons were born, Wilson says she took time off to move back to Virginia, where she could be near her parents. From 2016 to 2020, she was executive vice president, chief data scientist at L Brands, Inc., Les Wexner’s company that includes Victoria’s Secret and other retail stores.
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“They probably have the largest database of women consumers in the country,” Wilson says. So she went about building algorithms for marketing.
“There were not a lot of people in the boardroom who looked like me,” Wilson says. “So just like who my parents were, I decided I’m going to be an educator and a mentor. I walk the talk,” she says.
Indeed the talk recently is about the paucity of women CEOs and leaders in tech.
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The World Economic Forum reports, “The technology industry is booming – in the first quarter of 2021, global venture investments reached $125 billion (a 94% year on year increase). But if a rising tide lifts all boats, why has the inclusion and participation of women in tech not also shot up? According to the most recent Global Gender Gap Report, it will now take 135.6 years to reach gender parity, up from about 100 years in 2020.”
Built In concurs in a new report, “As the percentage of employed women across all job sectors in the US has grown to 47%, the five largest tech companies on the planet (Amazon, Apple, Facebook, Google and Microsoft) only have a workforce of about 34.4% women. While controversial technologies or flashy CEOs get most of the negative airtime, it’s the lack of women in the tech industry that seems to be the largest problem looming overhead.”
The statistics on women in tech are discouraging, Built In reports: Almost half, or “48% of women in STEM jobs report discrimination in the recruitment and hiring process. Black and Hispanic women, who majored in computer science or engineering, are less likely to be hired into a tech role than their white counterparts. In tech, 66% of women report that there is no clear path forward for them in their career at their current companies. Due to COVID, women in the tech industry were twice as likely to be furloughed or laid off than their male counterparts. More than half, or 54% of women say that the pandemic is making it harder for them to break into the tech industry.”
As a rare C-suite female-identifying leader in tech, Wilson says she has specific advice to give other women entrepreneurs and early career visionaries.
“It’s important to find your inner strength and inner courage,” she says. “When working in technology, engineering, math—STEM—you may not see ourself out there. But keep going at it. You have got to work hard and find your voice, your courage and raise your hand.”
She adds, “Before I became a CEO, I was an innovator and an entrepreneur. In the last four to five years I found, yes, I can be a brilliant CEO, and can constantly innovate. But having EQ, empathy and compassion,” is crucial.
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In her first six weeks as CEO of CLARA, that has 60 employees and is in a hyper growth phase, Wilson says she came up with two new products for the company whose products apply “image recognition, natural language processing, and other AI-based techniques to unlock insights from medical notes, bills and other documents surrounding a claim.”
“The biggest lesson is to stop and pause and make sure everyone understands the analytics and the AI and we are all together on this.”
She adds, “There are very few female CEOs in this field. I’m an anomaly.”