How Chief’s CTO, John Higginson, Leverages Technology to Create a More Equitable World

John Higginson, CTO, Chief

When John Higginson took on the role of CTO at Chief this past November, he became the first male executive at the private network dedicated to bringing more women into leadership roles by offering a platform to connect with other women executives. John may seem like a somewhat surprising choice for the role until you understand his journey.

Chief’s goal is to change the face of leadership—to have women fully represented, from VPs to board seats—by offering a network, tools, and programming that allow women in executive roles to connect across the country. As CTO, John leverages both his tech skills and his dedication to creating greater equity—a purpose firmly located, as Pete Wilkins frames it in Purpose First Entrepreneur, at the intersection of John’s strengths, his passions, and his commitment to using his power and influence to help others.      

According to John, his new role represents the culmination of a purposeful journey that started in his childhood. John sees his career trajectory as having been shaped by two driving factors—a childhood obsession with technology and its promise and the perspective gained from having been raised by a working mother.

At a young age, John fell in love with coding and all the things computers could do and make possible. He explains, “It was one of those rare historical inflection points. Mine was the first generation to know and use this technology, and that shaped my life.” When it came time to pick a course of study in college, John chose computer science and English. But in what would become a recurring pattern of following his instincts, he dropped the formal computer science major, which he saw as merely rehashing things he’d learned on his own, and instead focused on a degree in literature and storytelling.

In spite of dropping his computer science coursework, his first job out of college was at Applied Systems, then a technology start-up that sought to leverage the power of the personal computer to allow small insurance agencies to make use of technology in ways that had previously been prohibitively expensive. He started as a software engineer, then later took on his first leadership role and scaled to running multiple teams. When the technical co-founder retired, John stepped into the role of running tech at the company.

As he grew into these roles, he learned how much of leadership was about cultivating connections—learning to be a conduit for effective communication and brining stakeholders together. It was about technology, but it was also about storytelling. He recalls,

“One thing I found out about myself is that I really enjoyed being at the nexus of what the tech folks were creating and what the folks on the “business side” were interested in. I found that often those groups couldn’t communicate with one another; they just didn’t have a common vocabulary. So I could talk to the business folks and understand what they were trying to get to and explore possibilities, and then I could go back to the tech team and talk about what we needed to do, what we needed to build. That bridge-building was my first foray into leadership.”

While the very causal start-up environment might not have been the professional setting his mother envisioned for John, who was the first college graduate in his family, he says that many of the leadership lessons he implemented across his career came from watching his mother at work.

John grew up in the south suburbs of Chicago, the only child of a single mother. Having a mother who worked outside the home made John’s family dynamic unique within his peer group. His mother worked in the restaurant industry, a completely male-dominated field, as a restaurant manager. John worked for his mother throughout high school and college, though he points out, “My mom was hands down the hardest boss I’ve ever had—she didn’t want anyone to think she played favorites.”

Watching his mother’s example gave him a unique perspective on leadership. From an early age John saw women as leaders, breadwinners, and decision-makers. During his time working for his mother, he saw firsthand the challenges and inherent biases women in leadership positions faced. He recalls male customers demanding to speak to the manager and, when they discovered that she was the manager, turning to the male maître d’ for help.

He also saw how his mother acted as an advocate for women in the workplace. At the time, the dominant belief was that pregnant women needed to come out of the workforce—that they were either too fragile to too much of a liability. The policy at most restaurants was simply to let them go. That could have a devastating impact on their family finances. Many servers and hosts were women, and the nature of their jobs meant that they couldn’t afford to take time off, let alone step out of the workforce completely for the duration of their pregnancies. John watched his mother go to bat to change this policy at her restaurant, going so far as to quit when the owner initially refused. He eventually relented, and the policy changed.    

John wanted to take those lessons into the tech world—which was an equally male-dominated field—and use his leadership positions to leverage fairness in practices. When he became an executive, he made it his focus. He recognized that he had some measure of power in these roles and could use that to not only change the company but also to the change the industry and bring more women to tech. John explains, “I want to build great products, but I also want to build them with a team that is reflective of the world outside.”

He found that one avenue for creating more diverse teams was changing hiring practices at the companies where he worked. John shares that he’s focused on “making the way we recruit for technical roles less reliant on pedigree and years of experience and just more open because that’s a gateway to bringing more women into the team. It is helping women in tech organizations get off the ground and prosper.” In his last year at FTD, for example, all of his direct reports were women, some of whom were promoted into those roles and others who were hired into VP roles, a first for the company.

John also recognized that his leadership positions opened opportunities to advance greater gender diversity outside of his companies as well. One example is the role he played in helping launch the first Chicago Women in Tech conference during his time as CTO at Enova. The women on his team had an idea for organizing a conference that would bring together women in tech from across the city. That would be no small feat, especially since they were building the event from the ground up.

While they had plans to get sponsors and anticipated earning back some of the investment in ticket sales, they needed someone to underwrite the first event—with the understanding that the investment may or may not be repaid. John recalls, “They’d gone around and around, and I was sitting there talking to them about it at the company. And I said, ‘You know what? We’ll underwrite it, Enova will,’ because I had the power to write the check.” The event is now in its seventh year.

For John, that committed focus creates not only a framework for greater diversity but also better performance and results for companies. He explains, “Plenty of studies that show that gender-diverse teams and gender-diverse companies run circles around teams that are not diverse.”

John tells people there are three arguments for prioritizing diversity in hiring practices. Of course, there’s the moral argument—that it’s the right thing to do. But John points out,

“If all you care about is P&L, diverse teams outperform non-diverse teams when it comes to revenue and profit. If all you care about is problem-solving and the strength of the team, there’s plenty of studies that show that diverse teams are better at problem-solving because of that diversity of thought.”

In his new role at Chief, John sees the opportunity to leverage his skills and his purpose-driven beliefs about creating a more diverse tech community to help create that kind of change at scale. While networking opportunities are typically locally driven initiatives, Chief’s success has demonstrated the power of technology to open opportunities for acceleration and for creating a wider community of support and mentorship.

For John, that mission offers a powerful point of alignment with his own deep sense of purpose: “As I look back on my life and the things that drove me, the things I wanted to see change in the world, this fundamental need for equal opportunities, it culminates now in taking all the tech skills I’ve learned and this passion I have for that ‘better world,’ all in one job. So now my job is to build the network and the products that will make the world a more equitable place.”