Kimberly Wood, CIO, Guardsquare
“When I went into the military, they thought I’d be good for the Signal Corps and that’s where I was introduced to information technology. It was something I knew how to do and did well, and I wanted to do it.” I enjoyed it,” says Wood, who admitted after earning a bachelor’s degree in computer technology.
Wood rose quickly through the IT ranks after leaving the military and entering the civilian workforce. She says she knew early in her career that she wanted to pursue an executive position.
“I wanted a seat at the table, and I realized that I could make decisions as good or better than the people I was working for,” she explains. “It was also about being in an executive role because I love leading people.”
As CIO, Wood draws on her military experience to drive her IT operations. “I run my shop very tightly like a military command. Here’s what you do, how you do it, when you do it. Here’s how you communicate, here’s how we empower the team,” she says, noting that her leadership style isn’t as rigid as the military’s, but still provides structure. that is necessary to help all workers in their roles.
But being a woman in a profession where women are statistically under-represented has not been an issue for Wood. She says, “I can’t say that there is any obstacle in front of me.”
In addition, she sees more women applying for technical positions, especially on the product side.
As CIO Wood is focused on “supporting GuardSquare’s growth, enabling it to scale in an effective and secure way” while ensuring all employees can be their best. “I’m working to build empowered teams that can thrive with or without me. I guess that’s how you define success,” she says.
make way forward
S. Yvonne Scott is another female IT leadership pioneer who looked to technology early in her career as a way to fuel her career ambitions. Scott began his professional life as an IT auditor, an emerging discipline at the time he entered the workforce after earning a bachelor’s degree in general management and accounting.
S. Yvonne Scott, CEO, CIO Concierge LLC
CIO Concierge LLC
“I thought [the work] would tear me apart, and it proved to be true,” she says.
At the same time Scott developed an aspiration to become a business leader: “I wanted to be in a position that would influence the direction of the company. I wanted my work to be meaningful. And I wanted the opportunity to work on strategy.
Recognizing that “you won’t become an executive as an auditor,” Scott leaned into his tactical skills, forged ahead and eventually moved into a technical position. The timing was good, she says, at a time when technology was becoming “more and more important to strategy for companies”.
She worked for the railcar company GATX for 17 years in a series of increasingly high-level roles. She eventually became Vice President and CIO of GATX Rails and then Senior Vice President and CIO of GATX. The latter was a new position, the company’s first venture CIO focused on providing operational excellence and competitive differentiation. Scott was the first person to hold the title.
Scott acknowledges that gender has been a factor at points in her career. Initially she faced men who said they did not want women in leadership roles. On the other hand, they have worked with officials committed to creating greater gender equality and bringing women into leadership roles.
Scott is reflective and honest about how the timing of his career affected his ability to succeed. “If I had been born 10 years ago it would have been highly unlikely that I would have ended up in the position that I have,” she says. “Some of your career is determined by the circumstances in which you find yourself. You can only control it so much. You may be equally talented but not exposed to the right people or present for the right opportunities.
Scott left GATX in 2007 to become CIO of Crowe, an accounting, consulting and tech firm. She retired from that position in 2020. She is now the CEO of her own business, CIO Concierge LLC, a niche consultancy that provides executive-level coaching as well as IT branding and strategic planning services. “It’s a way of paying it forward and helping the next generation of technology leaders,” she says.
ready for the challenge
Monica Caldas, executive vice president and CIO of Liberty Mutual Insurance, credits a passion for technology and an early interest in problem-solving for setting her on the path to the executive suite.
She also credits determination.
Monica Caldas, EVP and Global CIO, Liberty Mutual
“As a child of immigrants, I learned that we are in charge of our own destiny,” she says. “I came to this country when I was young, and when we first arrived, my dad told me that America is a place of opportunity for those who work hard. That moment and many others helped motivate me.
After earning a bachelor’s in information systems management, Caldas joined General Electric, where she completed its technology leadership training program.
“Through that program I learned how to push the boundaries of problem-solving with technology,” she says. “It was a path that really kept me traveling and one that led to a 17-year career at General Electric in roles with increasing levels of responsibility, global perspective and leadership. [including CIO positions],
Caldas moved to Liberty Mutual in 2018, accepting a Business Segment CIO role to help the Retail Markets division accelerate a broader transformation effort. She explains: “I was blown away by the opportunity to help transform the insurance industry with technology and data in a very meaningful way.”
Caldas assumed the role of global CIO in January 2023, joining the company’s executive leadership team and overseeing a team of more than 5,000 engineers. She is the first woman to head the technology division of the company. None of this bothered him.
“Throughout my career, I’ve had roles that dealt with big, complex problems in different industries and parts of the world,” she says. “All the different roles I’ve taken on have been about pursuing the art of the possible and not settling for the status quo.”
Yet at the same time Caldas, like other female CIOs, recognizes the gender imbalance that persists in IT. She points to studies that show only 26% of technology jobs are held by women.
“As I step into the role of CIO as the first woman leading technology at our company, I think about how I approach the role. The demands of the job don’t care what gender orientation you are, she says. “However, as first lady, I also know that I have an incredible opportunity to inspire others, whether they are immigrants of different genders or if they are women who are unsure that they have Technology has a place. As such, my mission is first and foremost to continue to support the inclusive culture that we have for all people from all backgrounds to succeed in their own individual career aspirations.
Lucilla Rastelli’s CIO ambitions began early in her career, starting when she took a job at South African Airways right out of high school. She says company executives recognized her aptitude for math and computer science and offered her a position in the IT training program.
Lucilla Rastelli, CIO of Global Service and Supply Chain, GE HealthCare
“I quickly realized that I was focused on solving problems and helping people. And I fell in love with it, and the ability to solve problems,” Rastelli says. “I quickly recognized that technology It can also be very helpful in driving change, driving business results and helping people. So early on I knew I wanted to reach the top spot. I wanted to occupy the seat where I could have the most influence.
She achieved that objective in 2019, when she took her first CIO position at GE HealthCare. She moved on to her second CIO position at the company two years later and then became CIO of the company’s global service and supply chain in February 2023. She is the first person in the newly created position and is one of five CIOs at GE Healthcare.
Rastelli acknowledges some challenges as she built her career.
When she graduated from high school in her native South Africa, she could not afford college. However, she earned her undergraduate degree in the United States through GE’s tuition reimbursement program.
And she says she experienced some self-doubts. “One of the first obstacles I faced was my own impostor syndrome,” she says, explaining that when there’s a lack of female talent in the leadership ranks, you wonder if you belong. But I’ve also encountered some pretty strong support, and that’s enabled me to be fearless.”
Today as CIO, Rastelli is focused on “being able to deliver great business results for GE Healthcare, through technology aligned and enabling strategy. My focus will always be on how we can help GE Healthcare achieve its goals.” What can you do to help achieve that?”
She says she’s also focused on creating a workplace where her team can help achieve those objectives “in a way that brings people the most joy and most reward in their careers.” She strives to create an environment where employees can be their best selves and contribute to their maximum.
Rastelli says she is also aware of the need to bring more women into the profession and to retain those who enter but leave just as quickly as they do. And she challenges others to do the same. She recalls a recent networking event where she was the only female CIO among dozens of attendees. When it was her turn to speak, she presented a challenge to those present: “The next time we get together you have to bring someone who looks like me.”