by Charlotte Pinckney
Some leaders are born. Others are made through resilience, hard work, and an unshakable commitment to learning. Penny Collins, Insight Global’s IT Chief of Staff, is the latter. Her journey from a single mother struggling to make ends meet to a technology executive and advocate for women in tech is nothing short of extraordinary.
Penny’s career began in a place many wouldn’t expect—as an assistant at a technology company. Why unexpected? Penny knew nothing about technology at the time, let alone how to even turn on a computer. But she was determined to learn everything she could about the technology and her new company. Every day, if she heard a word in a meeting that she wasn’t familiar with, she wrote it down. Later that same day, she would rush to the library after work to check out books on technology and read while her daughter played on the playground. Penny immersed herself in the world of technology, absorbing every lesson like her future depended on it—because, in many ways, it did.
She faced relentless obstacles, including being close to homelessness. She had to make choices of whether to pay the electric bill or rent. But no matter how difficult life became, Penny showed up—every single day. Her consistency, resilience, and hunger to learn did not go unnoticed. A female leader at her company saw Penny’s potential and gave her the opportunity to be promoted to lead carrier relations. This role marked the beginning of Penny’s rise in technology leadership, and it certainly wouldn’t be her last.
From there, she kept pushing forward. When her company was bought out by a major telecom carrier, she transitioned to another telecom company, where she took on the challenge of building the company’s first Internet Operations Center. She didn’t have a background in project management or network operations, but that didn’t stop her. She went back to her roots—reading, researching, and teaching herself everything she needed to know to lead the team to success. Her work was noticed by the CIO of Security and Technology, who became her mentor and helped propel her career forward.
Over the years, Penny climbed the ranks, moving from manager to director, then VP, before eventually moving to London and becoming the Retail COO for the largest telecom company in London. She took on massive business transformation initiatives, proving time and again that her relentless work ethic and ability to lead people set her apart. But despite all her success, Penny never forgot the struggle of starting out as a single mother with no formal tech background.
It was at a major financial services company, where she served as Chief Technology Control Officer, that Penny found her true calling: helping women rise in their careers. She helped establish the company’s Women’s Leadership Council, which grew to over 5,000 members globally in its first year. During this time, she was also approached by a non-profit, Women in Technology (WIT) to become an executive sponsor and later dedicated five years outside the corporate sector serving as its President & CEO. Under her leadership, WIT grew from 20,000 to 58,000 members, raising over $3 million in sponsorships in the first year and launching initiatives that changed lives.
One of Penny’s proudest achievements is the Single Mothers Program, which she created at WIT. This initiative provided single moms who are living in poverty with technical training, childcare, transportation, meals, and mentorship to help them build careers in tech with all costs being covered through grants and fundraising activities. Thanks to the program, over 68 women—many of whom were once homeless—now have corporate jobs, earning six-figure salaries with benefits for their families.
Today, at Insight Global, Penny continues to lead with the same passion and purpose. She championed a scholarship through Insight Global for the WIT Single Mothers Program, awarding $10,000 to a woman demonstrating academic excellence and community impact. Even more inspiring, Penny hired last year’s scholarship recipient to work at Insight Global, bringing her story full circle.
Penny’s motto is simple: “You never leave a woman behind.” Her career is proof that with resilience, a hunger for knowledge, and a commitment to lifting others as you climb, there are no limits to what you can achieve.
Penny catching up with Allie Hunter, last year’s WIT Single Mother of the Year recipient, over lunch at Insight Global’s HQ in Atlanta.
by Jade Gilley 
by Julia Koslowsky 
