Humans of Tech | Shawna Stewart

Getting to Know Shawna

Shawna Stewart is the VP of People and Operations at Railz (acquired by FIS), a DMZ Advisor, executive coach, and speaker. In the tech world, she operates at the intersection of people and business strategy. 

Her work is hyper-focused on aligning talent with outcomes and empowering those on the ground floor to bring big ideas to life. It’s not just about managing operations or leading teams. It is about connecting the dots between vision and execution, helping individuals understand how their day-to-day work supports the broader goals of the business. Shawna ensures people have the clarity, tools, and support they need to deliver meaningful results.

“I work in HR,” she’ll say with a smile at dinner parties. “But it’s a fairly strategic role. I work closely with CEOs and founders on business operations and strategy, and I translate that vision to the people doing the work so they can see how they fit into the bigger picture, buy-in, and move things forward.”

What most people do not expect is just how strategic her role is. In many companies, HR is seen as either culture-focused or compliance-driven. Shawna bridges both worlds. She is a rare kind of leader who manages performance and values while also sitting at the executive table and helping drive outcomes.

A Career Built on Curiosity

Some careers follow a carefully mapped-out path. Shawna’s took a more unconventional route. Driven by curiosity and a hunger for growth, she built her journey by seizing the kinds of opportunities others might hesitate to take.

Prior to tech, Shawna was wearing many hats at an insulation company: managing inside sales, coordinating the office, and overseeing operations, all while running a teaching clinic for chiropractic interns. (Wears many hats, much?)

Tech drew her in with the tone and approachability of the job descriptions. Unlike traditional industries with rigid roles, tech offered evolution. “It wasn’t ‘this is the job forever,’” she recalls. “It was ‘this is where you start, and if you’re the right fit, you’ll grow.’” That sentiment was matched by her recruiter, who didn’t see the move as a leap into the unknown, but as an arena where Shawna’s skills could thrive. That spirit of possibility hooked her, and she has been growing ever since.

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Navigating the Unknown

One of Shawna’s defining career moments came when a new CEO arrived with sky-high expectations, assuming she already knew how to deliver on his ambitious vision. She could have panicked. She could have made excuses.

Instead, she met his asks with, “I’ll get that to you by Friday.”

Then she did what she does best: she figured it out. She researched, asked questions, and dove in headfirst. In that trial by fire, she emerged sharper, stronger, and more confident in her ability to navigate the unknown.

The biggest test came when that same CEO decided to step away from the business. The board turned to Shawna and a colleague and said, “You’re running the company… until we find someone else.”

All Shawna heard was: “You’re running the company.”

Together, they dissected the business, connected with customers, and turned chaos into momentum. Their leadership was not just about keeping the lights on. It was about building something stronger. The company was acquired under their leadership. 

That experience of turning uncertainty into action is one of her proudest career moments. And when she and her former team reunite, they always say, “Remember when we ran a whole company for a year and crushed it?”.

Showing Up Fully: Belonging, Identity, and the Power of Being Yourself

If Shawna could offer one piece of advice to her younger self, it would be this: “Don’t shrink to fit in.” She shared that early in her career, that is what she did.

She muted her curiosity. She softened her quirkiness. “I was avoiding standing out as a person of colour, especially as a Black woman,” she reflects. “I wanted everyone around me to feel comfortable - especially a board made up entirely of white men. I’d say things like, ‘We’re not putting lipstick on a pig,’ just to match the tone. But the truth is, I was shrinking. I was trying to fit into an environment at the expense of who I really was.”

Shawna confronted how much of herself she had been suppressing at work after the murder of George Floyd. The day after Floyd’s death, as her company continued with business as usual, she could not stay silent.

“I don’t understand how we’re going about business as usual.”

Shawna followed up with what needed to be said:

“Hold on a second. It’s not just about me,” she continued. “There are team members who identify as Black, who will feel discouraged by this silence. If my experience can be disregarded, how will you treat those who don’t have the same platform?”

She wasn’t looking for pity or sympathy, just honesty and recognition.

“I’m in a weird place right now, and it needs to be acknowledged,” she said. “I’m not here to tell you exactly how to respond. We need to figure it out together. But what we can’t do is pretend this isn’t happening.”

That conversation was not easy. It took vulnerability. It took courage. And it became a turning point, not just for the company, but for Shawna herself.

She realized she was done minimizing. Done making herself smaller so others could feel at ease. She began showing up fully and unapologetically. Not just for herself, but for her team, for the next generation, and for anyone who has ever felt pressure to hide who they are.

“This is who I am. This is my heritage,” she says. “I can communicate without thinking ‘Oh, no they’re going to see that I am Black.’ It got me out of my comfort zone but back into my comfort zone that is me.”

Today, she is intentional about creating that same space for others: a culture of psychological safety where people are not just seen, but celebrated for who they are. And while she remains cautiously optimistic, she is encouraged by what she sees, especially in the next generation.

“A lot of effort has been put in place to make sure we’re more aware. Even though DEI is being diminished in some spaces, the pause still happens because people are more informed,” she says.

Shawna co-owns a dance studio for youth and sees firsthand how passionate Gen Alpha is about justice and equity. “I love Gen Alpha’s attitude about social issues and how they’re activists. We are in good hands going forward. The knowledge is out there, and it’s being sought after. The momentum is real. The change is here to stay.”

Her hope is that more people find the courage and the support to stop shrinking and start showing up as their full, brilliant selves. As Shawna says: “There’s a reason you’re here. There’s a reason you pushed yourself to be here. Don’t doubt yourself. Pave that way for yourself.”

Navigating Tech Leadership

Shawna’s leadership philosophy is simple: “clear the path so others can do their best work.”

To her, leadership means removing bottlenecks, streamlining inefficiencies, and creating an environment where people can thrive. It is about clarity, trust, and purpose.

And when it comes to hiring, she looks beyond the resumé. The trait she values most: curiosity.

“I want to hear about a time someone built something from scratch, or spotted a problem and took initiative to fix it,” she says. “That tells me they’re thinking beyond what’s in front of them.”

When things start to feel stagnant, she shakes things up with hackathons, SWOT sessions, or collaborative brainstorms. Because in tech, it is not just about execution. It is about solving problems, pushing boundaries, and staying two steps ahead.

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The Future of Tech and Shawna's Big, Hairy, Audacious Goal

If Shawna could build one piece of tech today, she would not hesitate: an AI-powered, fully accessible app builder.

“A tool where I can describe what I want to build, and AI just creates it, no gatekeeping, no hidden fees, just creation,” she says. To her, the future of tech is about democratizing innovation and putting power into more hands.

As for her legacy, she has a BHAG: a Big Hairy Audacious Goal to help 50 people advance to their dream career. So far, she is at 11 and counting.

The ripple effect is real. Once, she heard someone on a podcast say, “One person who helped me get here was Shawna Stewart.” That is what drives her. Lifting others as she climbs.

At its core, Shawna’s journey is about showing up when it matters, staying curious, embracing discomfort, and helping others rise alongside her.

🔗 Connect with Shawna on LinkedIn: Shawna Stewart