When uncertainty swirled amid the evolution of AI several years ago, AI-powered skills development platform Udemy didn’t back away — it leaned in.
The company aspired to show its employees what AI could do for them, igniting a shift in perspective that has carried the organization to where it stands today.
“[Our employees] saw that AI wasn’t here to replace them; it was here to support them in doing their work more effectively,” Chief People Officer Karen Fascenda explained.
Team members across the company use AI to optimize the ways in which they collaborate, experiment, and, ultimately, find solutions. According to Fascenda, it’s not just limited to technical teams; HR team members, business partners, and administrators are reaping the technology’s benefits, changing how quickly they accomplish their work — and how well it turns out.
“Speed and efficiency are part of the story, but they’re not the whole story,” she said. “We’re looking at how AI is influencing the way people think and the quality of their work.”
As AI reshapes Udemy on an internal level, it’s also enhancing the company’s ability to help those who use its platform learn new skills and put them into action.
“We’ve embedded AI throughout our product ecosystem to deliver more value to customers,” Senior Director of Learning and Organizational Design Rebecca Stern said.
At Udemy, AI isn’t just a catalyst for temporary success. As Chief Information Security Officer Chad Kalmes put it, the company’s technologists are building new ways to create sustainable value with every tool they make.
“As a team, we’re taking a sprawling, complex operational landscape and turning it into a streamlined launchpad for acceleration,” he said. “Through our AI and automation work, we’re replacing slow, brittle, manual processes with intelligent systems that can anticipate needs, reduce drudgery and toil, and create clarity.”
How AI Unlocks Opportunity for Udemy’s People
As AI continues to transform how we live and work at an unprecedented pace, Udemy’s people must keep up. That’s where Fascenda’s team comes in.
“Learning has always been core to who we are at Udemy, and now AI is helping us personalize that experience in meaningful ways,” Fascenda said.
She and other people leaders at the company are looking ahead as they embrace AI as a partner rather than a tool, harnessing its power to create tailored development opportunities, identify talent needs before they become critical, and reimagine performance development. They even use the technology to model different future states, enabling them to develop proactive strategies for workforce development.
Fascenda noted that it’s also critical for her team to ask important questions like, “How do we ensure our systems reflect our values around inclusion? And how do we stay transparent when AI is influencing decisions?”
“These are big questions, but they’re the right ones,” she said. “They keep us focused on building systems that support people in fair and intentional ways.”
Additionally, Udemy’s Learning & Development team engages in monthly AI experimentation hours, during which they explore AI tools using safe data to evaluate potential applications, focusing primarily on the company’s existing approved technology stack.
“We’ve only scratched the surface of its full capabilities, so this time gives us space to safely test out what else our tech stack can do and what we want to cascade to the organization,” Stern said.
Stern, Kalmes and their cross-functional team applied their AI knowledge to roll out a companywide reskilling initiative. The initiative, composed of four distinct phases, began with foundational AI fluency work and has now progressed to the second phase, which consists of experimentation.
According to Stern, monthly “UDays” give employees space to learn about AI and apply their newfound knowledge to conduct experiments. Her team even gamified the experience by offering cash prizes to employees with noteworthy experiments, further encouraging team members to hone their AI skills.
Stern said they’re now preparing to advance to the third phase focused on functional-specific use case identification and development, which involves deeper collaboration with business units to identify existing workflows that could benefit from AI integration or complete transformation. To conclude the initiative, team members implement these new ways of working and take part in more reskilling efforts as their roles evolve.
These efforts stem from what Kalmes considers a “very deliberate philosophy” regarding the intersection of AI and data.
“We build intelligence into the core of our operations, not the edge,” he said.
“We build intelligence into the core of our operations, not the edge.”
Kalmes shared that the company aims to ensure its people can innovate with AI safely and quickly. That’s why every employee receives a professional development stipend and has access to AI platforms like Toqan, OpenAI, and Cursor. Leaders also encourage team members to experiment and share their knowledge with others across the organization.
“We firmly believe AI is a capability every team should be able to wield,” he said.
An Education in AI
To ensure its employees had the knowledge needed to embrace AI, Udemy created the “Generative AI Foundations Academy,” which was designed to establish a common baseline of AI literacy across the company. “Rather than treating this as just another training program, we approached it as a seismic cultural shift,” Fascenda said. “We wanted every ‘Udemate’ to understand not just what AI can do, but how it might reshape their roles and how they could proactively guide that evolution.”
To bring this initiative to life, Fascenda’s team worked with other departments to find a way to balance standardized learning with function-specific applications. She recalled how challenging it was to incorporate new AI developments in real time, which felt like “building the plane while flying it.” Nevertheless, all of that hard work was worth it, as it’s setting employees up to thrive long term. “We are becoming a skills-first organization,” Fascenda said. “‘Generative AI Foundations Academy’ accelerated that transition by helping us map emerging AI-related skills, identify gaps, and create targeted development opportunities.”
AI’s Impact on Learners
“Here, you don’t just ship algorithms; you literally shape how millions of people learn, grow and reinvent their careers,” Kalmes said.
Udemy’s employees have been transforming how people learn for more than a decade. And now, with the continuous evolution of AI, team members have created even more solutions with the potential to change people’s lives.
According to Stern, several of Udemy’s offerings reflect this AI-driven innovation. Udemy’s Skills Mapping feature, for example, allows learning and development teams to specify desired skills and automatically draft customized learning paths. Additionally, the platform has an AI Assistant that can help users navigate content, or provide real-time guidance and clarification on complex concepts within a course. Recently, the company launched an innovative, AI-powered Role Play feature, enabling learners to practice skills in simulated scenarios, reinforcing knowledge as part of the learning journey in an interactive environment.
Whether it’s a global enterprise upskilling thousands of employees or a professional trying to pivot careers, Kalmes explained, the AI features help surface the right content at the right time. With personalized learning paths, skills-based assessments, and dynamic, interactive upskilling experiences, these features take the company’s offerings much further than just a course library.
“For our customers, AI transforms what could be a static content catalog into a living, breathing learning and reskilling ecosystem,” Kalmes said.
“For our customers, AI transforms what could be a static content catalog into a living, breathing learning and reskilling ecosystem.”
As Udemy continues to keep up with AI’s evolution, the company is eager to lean into agentic AI and orchestration. Kalmes shared that the company is focused on learning how to stitch data, applications, and large language models together into secure, multi-system workflows that eliminate complexity for internal teams while driving better outcomes.
“That’s still largely uncharted territory, and it’s motivating to innovate and have impact where there isn’t necessarily a prescribed formula for success,” he said.
Kalmes noted that the company is also focused on AI observability, trust and policy enforcement, motivated by the notion that “innovation without governance is just chaos with better branding.”
With a focus on responsibility and experimentation, Udemy’s approach to AI is designed to foster long-term success for the business, filling in the gaps left behind by less powerful forms of technology.
“Without AI, we’d still be delivering impact, but at the ongoing and less-scalable costs of human bandwidth, innovation velocity and team morale,” Kalmes said. “With AI, we’re scaling clarity, empowerment and progress through Udemy.”
What Lies Ahead
AI isn’t just enabling Udemy to succeed here and now — it’s preparing the company to tackle what lies ahead.
“Whether it’s workforce planning or identifying shifting needs across the business, AI allows us to stay proactive and flexible,” Fascenda said. “We’re still early in this journey, but every step forward shows us more of what’s possible when we use AI to support, not replace, the people at the heart of the work.”
Stern is equally excited about Udemy’s path to becoming an AI-powered company. This AI-powered directive empowers team members to bring their creativity and passion to work every day to improve the lives of the organization’s customers, instructors, and employees.
“No matter what function you sit in, AI will be part of your work,” she said. “Someone who embraces AI and is excited about the potential it unlocks in the ways we work as well as the ways we learn would be a fantastic fit for our company.”
From Kalmes’ perspective, Udemy wouldn’t be where it is today without AI; the impact would still be there, but the “clarity, empowerment and progress” would not. Nevertheless, that doesn’t remove the need for human intelligence — rather, it demands it.
“We know that the future isn’t purely technical; it’s inherently human,” Kalmes said. “Teams who understand both will build the most transformative AI solutions.”
“We know that the future isn’t purely technical; it’s inherently human.”
For him, the work currently being done with AI is akin to “rebuilding the nervous system of the company.” Prior to this newest phase in the company’s AI journey, teams often acted as isolated limbs, moving independently yet out of sync. But through process redesign, embedding AI, agentic workflows, and unified data orchestration, the company is creating coordinated reflexes powerful enough to send it across the finish line.
“The organization can instinctively respond like a trained athlete, rather than just react — that’s a sea change,” Kalmes said. “I am very proud of the craftsmanship and thought involved in everything we’re doing, as we’re making sure we are doing things right, not just fast.”
