Rebuilding Legacy Brands: How O’Reilly Reinvented Itself for the AI-Powered Future

When you think of O’Reilly, chances are you think of the iconic tech books—the ones with the animals on the covers that taught generations of developers to code. But behind that beloved brand is a company that has undergone a remarkable transformation. Twice.

In our recent Game Changers session, we sat down with Allison Gillespie, VP of Marketing at O’Reilly Media, to talk about what it takes to evolve a legacy brand into a modern SaaS business—and what’s next as AI reshapes the learning landscape once again.

Here are some of the top lessons from her 19-year journey of leading through change.

From Books to SaaS: The Power of a Clear “Why”

O’Reilly’s pivot from publishing to a learning platform began in 2017. The company had already built trust over decades in the tech world—but that trust was tied to physical books and conferences. As the world moved online and learning behaviors changed, the team knew it was time to shift.

The solution? A subscription-based platform that offered not just books, but live trainings, videos, interactive tools, and curated content.

But the transformation wasn’t just about product. It was a cultural shift—from transactional selling to long-term value. And from Allison’s perspective, the success of the transition hinged on one thing: a deep understanding of the audience’s “why.”

“The audience is still the same. They’re still learning. Their needs just shifted—and so we did too.”

Content for Humans (Not Just Buyers)

O’Reilly’s marketing strategy didn’t rely on hype. Instead, Allison and her team focused on what their technical audience actually wanted: real, usable content.

“Instead of telling people how great our content is, we let them experience it. Ungated. Hands-on. No fluff.”

They ditched the jargon. Embraced education. And let prospects sample the learning platform through live training sessions, not just whitepapers. It’s marketing by way of value—not volume.

AI Isn’t a Trend. It’s a Transformation.

O’Reilly has been investing in AI for years, but unlike many companies, they’ve avoided the “spray and pray” approach. As Allison puts it:

“Everyone was slapping ‘AI-powered’ on everything. But we wanted to be thoughtful—what’s actually helpful to our users?”

Today, AI is driving O’Reilly’s product roadmap. From surfacing the right content at the right time, to building custom experiences based on user behavior, AI is shaping the next evolution of learning. And internally, it’s enabling the team to experiment, automate, and even rethink tools they previously relied on.

Leading with Trust, Curiosity, and Candor

Perhaps the most powerful theme of the conversation was leadership. Allison’s take? Be transparent. Stay curious. And empower your team to experiment—even if they fail.

“You don’t have to have all the answers. But you do have to create a space where people can try new things. That’s how you keep your team—and your business—growing.”

Through massive pivots, the rise of AI, and constant change, Allison has stayed focused on people. The result? A team with incredible tenure, a culture of trust, and a brand that’s still evolving without losing what made it great.

Final Takeaway: Legacy Is Not the Enemy of Innovation

O’Reilly’s story proves that legacy brands can thrive in fast-moving markets—if they stay grounded in their audience, their values, and a willingness to evolve.

For anyone leading a team through change, experimenting with AI, or trying to shift brand perception, Allison’s advice is simple:

“Get outside your bubble. Stay curious. And don’t be afraid to say, ‘We don’t know—but we’re going to figure it out.”