Women IT leaders on their climb to the top

Three accomplished women share their experiences charting paths to the C-suite and the insights they’ve learned about changing the equation for women CIO aspirants in a male-dominated field.

For women who aspire to leadership roles in IT, the climb to the top can be particularly arduous — and lonely. Just 28% of IT leadership roles are filled by women, according to DDI’s 2023 Global Leadership Forecast, and many women end up leaving IT careers due to workplace culture, pay equity, microaggressions, and a lack of forward growth and promotion, among other uphill challenges.

As a result, making it to the top as a woman in IT requires more than just the right skills and experience. It requires confidence, mentorship, and a continued commitment to remaining open to new challenges and opportunities — despite at times difficult odds. For those women who do break through to the top ranks of IT, many feel compelled to help change the equation for those rising behind them, as well as women and girls who might otherwise not feel a career in IT is for them.

Here, three accomplished women leaders in the tech industry share their experiences, shedding light on what it takes to advance into a leadership position in a male-dominated field, as well as insights they’ve learned along the way that can help change the norms that work against women seeking to advance their careers in IT.

Inspiring an interest in tech

To foster more women in leadership positions in the tech industry, there needs to be an early focus on showing girls and young women that technology is a viable potential career path, says Lorrissa Horton, senior vice president and chief product officer for Webex at Cisco.

Horton herself drew inspiration from her mother, who went back to school to become a computer programmer after their family moved to Canada from the Philippines at a time when the ratios of women to men in IT were even worse than they are today — especially in mainframe computing.

Lorrissa Horton, SVP and CPO for Webex, Cisco

Cisco

Horton gained exposure to early technology through her mother’s career, and she recalls giant cell phones and modem-connected laptops as some of her earliest memories of tech. For Horton and her three sisters, watching their mom take on a full-time career in IT made an impression, as they all now work in technology careers. After completing a degree in computer science, Horton went on to work for Microsoft for 13 years, later moving on to Cisco, where she has now been for five years.

For Horton, getting ahead in IT has required being open to a wide range of challenges and experiences.

“I’ve done a little bit of everything,” she says. “I’ve owned the AI teams, the client teams, service teams, and I’m GM for two businesses — the calling and contact center businesses — and I’ve managed teams upwards of 4,000 people across developers, designers, PMs, etc.”

Tamecka McKay, CIO for the City of Ft. Lauderdale, had an early interest in tech as well — she was known in her neighborhood for beating Ms. Pac-Man, something she attributes as laying an early groundwork for her career. McKay didn’t originally intend to pursue IT — her plan was to attend law school, but while working at a law firm in her early 20s, she met a colleague who “saw where technology was going before everyone else did,” she says.

This colleague, and early mentor, advised McKay to explore a career in technology, so McKay enrolled in a Microsoft certification program, planning to work a service desk job while completing law school. But as IT and technology took off, so did McKay’s passion for tech, and while she “didn’t have the extensive technical background” of her colleagues, she had “book knowledge, excellent organizational skills, and customer service skills,” which helped her on the path to executive leadership.

Tamecka McKay, CIO, City of Ft. Lauderdale

City of Ft. Lauderdale

The path to leadership

Debbie Stephens, deputy CIO of the USPTO, started her career on the business side, where she learned how important it is to engage team members, fully understand processes, and see how technology can help improve business outcomes.

After moving up to associate commissioner for the patent information management team, Stephens helped assist the digital transformation of the USPTO, becoming a liaison between the CIO and the business side, guiding IT implementation. And it’s this experience, she says, that allowed for a “natural transition to my current deputy CIO role,” as she understood what makes a team function, knew the tools being implemented, and had a strong sense of the business side of things.

Debbie Stephens, deputy CIO, USPTO

USPTO

Ft. Lauderdale’s McKay says she didn’t have her sights on a CIO role when she started working for a local government agency in 2001; she simply wanted to “do a good job.” There, however, she fell in love with public service and technology, inheriting a team she describes as “disparate, disgruntled, and unstructured,” with a poor culture and environment for success. She was wary, but she’d learned from her master’s degree program in public administration that the key to building a strong team was “putting people first, being compassionate, being transparent, sometimes being vulnerable,” she says.

Within four years her team became one of the highest-performing teams in the IT department, giving her the confidence she needed to see herself as a strong IT leader.

“As woman, and I can’t speak for everyone, but as someone who’s struggled with insecurity, sometimes imposter syndrome, wondering if people think if you’re good enough — that growth really helped me believe in myself and gave me that confidence to step into a leadership role and consider myself a true leader,” she says.

That job as IT manager for the Town of Davie, Florida, led McKay to her next role with the City of Ft. Lauderdale, where she started out on the infrastructure side, “building that trust, empowering and setting people up for success, and making sure that they know that they’re valued and that they’re trusted.”

Her success in growing this team led to her being offered the CIO position.

McKay faced significant challenges starting three months into the role, when her team experienced a major file server outage, “putting the departments literally at a standstill,” followed by a citywide network outage three months later. As if that wasn’t enough, not long after that, Ft. Lauderdale experienced historic flooding, “rendering the entire city hall inaccessible.”

“I can truly say that I now accept and embrace what I bring to the table — that may be different than your typical CIO, who probably doesn’t look like me, probably doesn’t sound like me, and probably doesn’t think like me. But I realized that’s exactly what we need,” says McKay of her experience persevering through those early challenges.

USPTO’s Stephens notes that mentorship is vital both to supporting women in the technology industry and encouraging them to embark on the path to leadership. As she’s mentored other women in IT, Stephens has noticed a stark difference in how men and women perceive their qualifications for job openings.

The women she’s mentored often undervalue their own capabilities, shying away from job opportunities that might feel out of reach or require a few skills they don’t have on their resume. Whereas men often feel the opposite — quite confident about their qualifications for a role, and less likely to focus on the qualities they feel they lack. She advises women not to undersell their own abilities, and to “be confident in their ability to provide value.”

Stephens also regularly asks for feedback from her employees, checking in to gauge how her tone and communication style are received. She welcomes constructive criticism and is eager for “stretch moments” as a leader, seeing it as a chance to learn and grow to become an even stronger, more effective CIO.

Along with mentorship, sponsorship is important for paving a path to leadership for women in IT. McKay remembers a moment as a manager when, in a room full of CIOs and directors, she was asked to take notes. The CIO at the time stood up for her, denying the request and reminding others that McKay was not an administrative assistant. That moment has stuck with McKay, showing how important it can be for women and underrepresented groups in technology to have an advocate and sponsor in the room.

“That was a poignant moment for me where I realized it’s very important to have those advocates and sponsors to keep everybody in check. And again, it’s not that people are bad or ill-willed. I’m good at taking notes. I’m good at organization. I think it was just natural that he did that. But I wasn’t there for that — I was managing an enterprise infrastructure team, which was a key component to the initiative. We were moving forward. And that’s how I should have been viewed,” she says.

Authenticity and transparency in leadership

Stephens is sensitive to her employee’s lives outside of work — understanding that there’s a delicate balance and that women are often tasked with additional childcare, homecare, and eldercare responsibilities outside of work.

“I’m very conscious of our team members who are balancing family — so often that falls on the woman in the relationship,” she says. Despite progress in society, Stephens says she still finds that the women in her office are typically the ones to handle home-related duties and are often juggling extra responsibilities such as childcare and eldercare.

She encourages her employees to take breaks, whether it’s 5 minutes at the end of a 30-minute meeting or 10 minutes after an hour meeting. She also encourages her employees to take longer breaks during their days, and to get outside and pursue the things they love. Stephens herself sets that example for her team by taking 30 minutes to an hour during the day to practice her hobby of inline skating — it’s her time to get fresh air and exercise and to unplug from the workday for a bit.

As a leader, Cisco’s Horton makes it a point to normalize being a working mom, and “dispelling myths that executives have perfect lives,” devoid of children, family emergencies, or just home-lives in general. Horton tries to be transparent about the priorities in her life — her family being first, followed by her responsibilities as an executive.

She wants her employees to feel comfortable bringing their whole selves to work and doesn’t want employees to think they have to hide their personal lives. She has brought her children to conferences out-of-state, even bringing them along on work dinners. At a recent dinner in Norway, colleagues were welcomed to bring their children along, noting it was the first time many of them had done so.

Horton’s perspective is that if she’s asking people to take time away from their children and families — especially after work hours — it’s only fair to let them bring their families along. She says it helps “drive a higher level of empathy,” connecting with coworkers and their families, and helps put things like family emergencies into perspective when they crop up in the workplace.

“We’re really starting to change some of those norms — it’s not uncommon for my kids to interrupt in the middle of a meeting when they come home after school. And my team knows it’s going to be a five-minute disruption and they’re going to leave. As long as we’re not disrupting or stopping the flow of actual work, I think it’s perfectly fine. And we see it from other people on my team and we completely welcome it,” she says.

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