Celebrating 2026 SaaS Trailblazers: The Women Redefining Leadership in the Next Era of Software

While the gender gap in technology remains wide, women continue to push the software industry forward with clarity, conviction, and a willingness to lead through uncertainty.

Their stories reveal not only how leadership is changing, but also how the next era of SaaS, defined by AI, speed, and constant reinvention will reward adaptability, customer obsession, and a commitment to building companies that last.

For our annual celebration of International Women’s Day, we asked our 2026 trailblazers how they’re making today’s rapidly changing world of software their own.

How has your definition of success changed as you’ve grown as a leader?

Business success is often defined by numbers in a spreadsheet. But SEG’s Trailblazers are moving toward a more holistic perspective grounded in long-term impact.

It’s a shift April Stiles, CEO of Perspecta, LLC, has embraced.

“Early in my career, success was largely defined by financial metrics, such as growth rates, revenue targets, and profitability. Those measures still matter, but over time my perspective has expanded,” she said. “Today, I define success by long-term, sustainable impact. Growth without durability isn’t real success.”

For Allison Yazdian, CEO of Uscreen, the definition of success has become “much more personal.” “It’s no longer just about outcomes or milestones. It’s about how present I feel, how clear I am on what truly matters, and whether I’m spending my time intentionally, both at work and with my family.”

Rachel Tipograph, CEO and founder of MikMak, echoed that intentionality. “I used to be obsessed with the end goal, and now I have shifted to simply enjoying the journey.”

Learning is also a part of success for many, including Laurie Smith, co-founder of Studycast. “Success is more about failing daily. Learning from others and enabling others to find the solution is where the reward lies.”

“In its simplest form, to me, success means being able to have an impact every day and being invited to come back the next day,” said Nathalie Garcia, CEO and founder of Practice Better. “It essentially means earning the right to be there, whether that’s for your customers, your team, your partners, or your family and friends. And I’ve been incredibly lucky to love it and to do it with incredible people and with wonderful support.”

What’s a leadership lesson you learned the hard way that still shapes how you lead today?

Becoming a trailblazer isn’t easy. “Every day you can experience the highest highs and the lowest lows in a matter of moments, and you just have to be ready for it,” Garcia said. “You have to be ready for everything and anything, and it tests you. Because you have to handle it, whatever it is, for your customers, for your team, for your partners, and there isn’t a lot of space to deal with it for yourself in those moments.”

Several of this year’s trailblazers talked about the importance of trust in the leadership equation.

“When I first stepped into leadership roles, I was focused on solving the problem directly in front of me as quickly and efficiently as possible,” Stiles said. “That mindset can absolutely drive short-term wins, but what I learned over time is that being purely transactional doesn’t build lasting trust.”

“Don’t skip the relationship work,” Yazdian said. “I learned that trust built early becomes your greatest leverage later. When the foundation is strong, you can move quickly and navigate hard moments with far more ease.”

That includes honest feedback. “More often than not the person already had a sense of what’s not working, and getting the issue out in the open allows for a much quicker and more productive path forward,” said Leigh Sevin, CEO and co-founder of Endear.

And ultimately, being a strong leader also includes being honest with yourself.

“One of the lessons I’ve learned is that leadership is not about having all the answers, it’s about being ruthlessly honest about what you don’t know,” Kathleen Barrett, CEO of Backlight, said. “If you’re slow to recognize your own gaps, or the gaps on your team, the organization slows down with you.”

Meet the 2026 Female Trailblazers of SaaS

Can you share a moment when you had to advocate for yourself, and what you learned from it?

“Unconscious bias is real, as a woman. You need to know your market worth and hold firm with it,” Tipograph said.

That requires some comfort with risk, Stiles said. “Putting yourself out there means accepting that not every idea will land perfectly, but growth only happens when you’re willing to raise your hand and say, ‘I’m ready.’”

Stiles stepped into executive leadership at a relatively young age, including serving as a vice president and later as president in her 20s. She quickly learned that advocating for herself wasn’t just about speaking up.

“I never wanted to stay confined to one ‘lane’ and that meant learning across functions, asking questions other might not ask, and developing a foundation that connected strategy, operations, finance, and product,” she said.

For Garcia, advocating for herself means also asking the questions that feel “silly” and saying, “I don’t know” so she can better understand all perspectives and leave space to be wrong and learn. “It’s also communicating my non-negotiables around making the time to take care of my mind and body during an already busy week and sharing confidently where I need help or how I work best.”

What customer insight most meaningfully changed your product, strategy, or company direction?

The conversations you have with your customers can reveal whether your strategy is aligned with expectations. “My biggest insight came from truly listening to our customers,” Stiles said. “I’ve consistently heard they want us to be consultative partners, not just salespeople.”

Customer feedback also led to a big revelation for Barrett, who leads an AI-powered software for managing and monetizing media. “One of the most important insights we heard from customers was that media can no longer sit in a system of record alone. It has to become a system of action, and increasingly, a system of intelligence,” she said. “The real value of content depends on how easily it can be seen, accessed, understood, and reused across the organization.” What once looked like flexibility in the form of offering separate tools and workflows now creates friction in the eyes of customers. She said that changed the company’s direction.

Garcia has had a similar experience. “We’ve typically been pulled into our biggest opportunities rather than needing to force them. Staying close to these signals and building trust and a strong relationship with our community of customers is what has made that possible.”

Has AI meaningfully changed your product, roadmap, or how your team works? If so, how?

“The use of AI permeates through everything we do,” Tipograph said.

It’s a sentiment echoed by the other Trailblazers, whose companies are using AI to understand complex data, provide additional context to customers, and speed product to market.

“Usually there’s a tradeoff between time vs. quality, but if you use it right, AI can improve both at the same time,” Sevin said. “Our product helps our customers more quickly identify the right customers to reach out to and guides them on what to say.”

Its deployment is similar at Perspecta. “Our AI strategy is tightly aligned with our clients’ priorities. We’re not pursuing AI in isolation, we’re advancing the same use cases and responsible-AI principles they are, ensuring our roadmap directly supports their future state,” Stiles said.

AI has raised the stakes for Barrett’s customers. “Many of the media organizations we serve are trying to balance two priorities at once: moving faster through AI-driven workflows without compromising editorial integrity or the creative judgment that defines their brand. That tension has meaningfully shaped our roadmap.”

The one idea all our trailblazers agree on is that AI is no longer optional.

“We believe, ‘If you’re not at the table, you’re on the menu,’ so we’ve gone full speed ahead to ensure we’re ahead of the curve on AI,” said Kam Phillips-Sadler, CEO of KidKare. “My team demoed something they’ve been working this week with AI that we’ll roll out to customers, and I actually teared up on the call. We’re at a critical inflection point for mind-blowing development.”

When you look ahead, what do you see as the biggest challenge or opportunity for software leaders?

The blazing pace of change is top of mind for our trailblazers; AI is the culprit.

“Being ‘ahead’ today can feel like being behind tomorrow,” Garcia said.

AI has changed the nature of competition, according to Tipograph. “AI has lowered the barrier to entry to building software, which means the hardest part of the game is going to be customer acquisition and servicing customers. Software leaders better get great at that.”

While disruption can be uncomfortable for some, it “has always been a constant in technology,” Stiles said. “The productivity gains are real, but AI has no judgment, no ethics, and no accountability on its own. The challenge is turning it into a trusted capability through strong governance, clear guardrails, and human oversight.”

Phillips-Sadler offered advice: “To run your own race, block out the noise and get diligently focused on the things that matter, while upskilling and not getting left behind.”

What do you want to do next as a leader, builder, or operator?

“I love every aspect of building and running a business, and I’m far from ready to retire. The future is full of opportunity,” Stiles said. For Perspecta, that means continuing to focus on “transforming healthcare technology in ways that truly impact patients and providers.”

Barrett also highlighted the desire to have a broader impact. “In the near term, I’m focused on building Backlight into a durable, sustainable business at scale. That kind of work is deeply motivating to me, not just because I love to build, but because I care about building something that has real impact.

“More broadly, I’m driven by the idea of leaving things better than I found them.”

Yazdian wants to help others achieve their dreams. “It’s the through line of my career,” she said. “As work changes, more people will bet on themselves. The opportunity ahead is to equip this next generation of builders with the tools, support, and leverage they need to create meaningful, lasting businesses. That’s the work I’m excited to keep doing.”

Thank you to the women who shared their experiences and to everyone who took the time to nominate them. Their leadership, insights, and impact continue to push the SaaS industry forward.

Nominate a Female Trailblazer in Tech

Join us as we celebrate International Women’s Day every March! We are always on the lookout for incredible female trailblazers in software, SaaS, and AI. If you know a woman who’s making waves in the industry, nominate her for next year’s submissions. Help us shine a spotlight on the inspiring women shaping the future of technology.