Podcast Summary “Reshaping L&D Through AI and Social Learning with Topher Olson of RealPage, Inc.”
From Classroom to Corporate: Topher’s Unexpected Journey
Topher Olsen didn’t set out to be a corporate learning leader, he set out to be a school principal. After years as a classroom teacher and earning a second master’s degree in educational administration, Topher found himself on an alternate path when Texas froze school administrator hiring. But in what he now sees as a fortuitous turn, he discovered the corporate training world, where he could merge his love for education with a new passion for upskilling adults in the workforce. Now the Vice President of Training and Enablement at RealPage, Topher leads a global team responsible for customer training, internal enablement, content development, and even managing a learning management system they license externally. It’s a big job, and one that reflects the depth and versatility of his experience.
The AI Shift: A Defining Force in L&D
When asked about the biggest changes in L&D in recent years, Topher doesn’t hesitate: “AI.” After attending an Artificial Intelligence (AI)-focused LinkedIn conference, complete with a self-driving car experience, he came away convinced that artificial intelligence is transforming how people learn, work, and absorb information. He’s bullish on the power of new AI tools, but also cautious. “If we dismiss it as a fad,” he warns, “we’ll be left behind.” He’s focused on how his team can use AI thoughtfully: to reduce cognitive overload, deliver just-in-time learning, and personalize content delivery, especially within RealPage’s own software.
Learning at Work Should Look Like Learning in Life
Topher posed a powerful question during the conversation: “Why do we learn at work differently than we learn in life?” We live in a world of TikToks, YouTube how-tos, and bite-sized content. But traditional workplace learning often still looks like long eLearning modules or clunky LMS experiences. Topher wants to change that. He envisions more dynamic, just-in-time learning, served up when it’s needed most and embedded in the flow of work. He shared that RealPage is investing in embedded AI tools to make this vision a reality, and he emphasized that training must be more than a one-time event. “Taking a course doesn’t mean you can do the thing. It has to translate to performance.”
On Metrics, Mentors, and Multifaceted Talent
A key theme in Topher’s approach to learning is impact. He insists that training should be tightly aligned with performance metrics. “If we’re not changing behavior or improving results, it’s a waste of time.” And to meet those demands, he’s building a team of Swiss Army knife L&D pros, people who can design instruction, facilitate in-person and virtual training, and understand how to use tools like AI to enhance their work. His reasoning? Budgets are tightening, and the days of having separate people for every task are fading.
He credits much of his leadership philosophy to a former mentor, Stephanie Nascimento. When he nervously approached her about leaving her team to pursue a national training role, she responded with, “What do we need to do to get you there?” That spirit of support and empowerment left a lasting impression, and it’s one Topher now tries to replicate for others in their own L&D career journeys.
What Every Learning Leader Should Read
Topher recommends The Power of Moments by Chip and Dan Heath. While not an L&D-specific book, its message resonates deeply with him: learning experiences are often people’s first impression of a company, a product, or a team. “We get to create those moments,” he says, “so let’s make them meaningful.”
He also embraces continuous, informal learning, favoring LinkedIn Learning, TikTok, and YouTube for quick-hit insights and inspiration. He’s currently following AI expert Allie K. Miller and thinks learning leaders should spend less time worrying about books and more time curating bite-sized, actionable insights.
Final Thoughts
Topher Olsen is a grounded, thoughtful leader who’s helping to redefine what modern learning looks like. From championing AI to insisting on performance alignment to modeling mentorship, he’s pushing the industry forward while staying true to his roots in education. His vision is clear: learning should be accessible, relevant, and transformational, not just a checkbox on a to-do list.
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