Reskilling and Upskilling for the AI Age
Real-world lessons from Udemy and Zapier on reimagining talent and building skills-based organizations
Check out the brief show notes following today’s lead column!
While most companies are still wading through AI hype, Udemy and Zapier are busy transforming how work gets done. Their secret? A concerted effort on two fronts: skills-based talent development paired with practical AI integration. The non-negotiable first step? Leaders rolling up their sleeves and mastering these tools themselves before asking teams to change.
"What we learned from our external research is that employees don't feel like their leaders have the skills they need to lead through the transition to using AI," Karen Fascenda, Chief People Officer at Udemy, explained during a recent Work Forward Forum discussion. "We've had a ton of focus on how to get leaders comfortable with AI and really build their skills to be change leaders."
Meanwhile, at Zapier, customer support teams have dramatically transformed their operations through AI, creating what Chief People Officer Brandon Sammut calls "elite teams with elite skills" that deliver higher performance – while also increasing pay and providing a better long-term career path for employees.
Both companies have discovered a powerful truth: as AI rapidly changes the nature of work, organizations need a skills-based approach to identify, develop, and deploy talent. Their journeys offer valuable lessons in how to navigate this shifting landscape while bringing employees along as partners rather than casualties.
Karen Fascenda, Chief People Officer at Udemy, and Brandon Sammut, CPO at Zapier
Rethinking Jobs from the Ground Up
Over the past year, Udemy has been systematically dismantling traditional hiring approaches focused on degrees and credentials, replacing them with skills-based evaluation. This shift didn't come easily.
"We switched all of our job descriptions last year to be skills-based and we made few exceptions," Fascenda shared. "It was hard to get many of our leaders to move off of degrees. We had conversations about the skills that a degree represents: let's break it down. Let's really talk about when you think about someone who has a computer science degree, for example. What does that mean to you? How can we interview for those skills?"
The transformation extended far beyond job descriptions. Udemy redefined how they evaluate talent:
"In the past, HR professionals talked a lot about competencies. I rarely hear people talk about competencies much anymore," Fascenda explained. "The way we define it, competency is the overarching job family. And then within competency, there’s knowledge, skills and abilities. Knowledge—how do you do it? Skill–can you be observed doing it? Ability–do you have the capacity to do that?"
This clarity allowed Udemy to make concrete assessments of what skills really mattered for each role. The impact was immediate and dramatic in hiring and internal mobility.
The Internal Talent Revolution
One of the most significant outcomes of this skills focus has been a transformation in how Udemy views its own talent pool.
"We shifted from 'it's my employee' to 'it's our employee'," Fascenda noted. "We had someone on the recruiting team last year move into a compensation role. They were doing all the recruiting for the sales team. They understood sales comp better than anyone in the compensation team. They also had a degree in economics. They've made the transition over to compensation, and they're like one of our best, highest performing employees now."
This wasn't an isolated success. "Last year, 37% of our internal jobs were filled through internal transfers, like really looking at the skills people had and how we moved them into our organization," Fascenda proudly shared.
The approach extended to how Udemy develops and rewards its people. Each month, the company holds "U-Day"—a dedicated day without meetings where employees focus on skills development. Recent curriculum has included "writing engineering prompts for AI" with significant rewards for the best performers.
"One of the winners got a cash reward...They wrote a prompt to do a better job of doing executive business reviews with all of their customers that then someone else took and made it the template for our executive business reviews," Fascenda explained. "We mapped all of those awards to a small cash incentive and gamified it. Then we also mapped it back to our core values."
Leading Through AI Transformation
Perhaps most enlightening was Udemy's discovery about what employees truly need from their leaders during this period of AI transformation.
While Udemy research found that 88% of employees felt effective leadership was critical for generative AI initiative success, only 48% felt executives were ready to lead those efforts. Given that external data, "We've had a ton of focus on how do we get leaders comfortable with AI, how do we help enable them to lead through this transition to using AI more, and helping really build their skills to be change leaders."
The approach is refreshingly practical. Udemy's leaders learn the basics of AI tools themselves, removing the mystery while establishing clear guardrails. This includes understanding ethical AI use, preventing data leakage, and enabling confidence. They enable learning through individual personalized modules, cohorts, and group classes.
"The first phase has been how to help them use it in their workflow. The next phase will be how to enable their teams to use it," she explained. "We're asking leaders to also start thinking about how they can automate the work with their team to help their team use AI into their flow of work as well."
Each function at Udemy has found its own applications – from marketing using AI for better SEO and personalized campaigns to HR automating cumbersome processes. They're even exploring AI-assisted interview analysis, though they're carefully navigating the legal considerations.
The Future of Work is Reskilling (not Downsizing)
With AI rapidly changing job requirements, the big question looms: what happens to existing employees?
"The biggest thing that we've been saying is that AI can help take some of the menial tasks out of our work and help work with us. We have to learn how to use it. If we don't, we're going to fall behind. But we believe in re-skilling," Fascenda emphasized.
This philosophy aligns with approaches at other forward-thinking companies. At Zapier, a similar transformation is underway. Their customer support leader took a remarkably transparent approach with her team:
Eighteen months ago, Lauren Franklin, Head of Support, told the team that “We’re raising the bar to become a high-performing Support Org—scaling efficiently while delivering even better customer support.”
Lauren was empathetic, but also candid. Performance expectations were rising, including for herself. She was clear that the plan to meet these higher expectations was about smarter tooling, upskilling, and AI, rather than about overwork or compromises in support quality.
She also led by example: Lauren was in the support ticket queues first thing every Monday, helping customers directly to understand firsthand the tooling and process improvements that her team needed to adopt and see what was really working, and what wasn’t.
Zapier CPO Brandon Sammut shared the results: "And guess what? Lauren and the team figured it out. Metrics like average ticket handle time are meaningfully improved, and the team's employee engagement scores are up by 20 to 30 percentage points in many areas. It's amazing," Sammut reported. "Zapier's support team is becoming truly elite, and Lauren pays her team top decile salaries to reflect that excellence."
Zapier’s thoughtful approach where leaders get elbows-deep in the reality of AI-enabled tools and process change has led to 89% of employees using AI in their day-to-day work.
Their approach echoes Shopify CEO Toby Lütke's recent memo, which made an explicit promise not to cut jobs due to AI but made clear that employees needed to embrace these new tools. As Fascenda noted, "It makes sense, right? How do we think about building our own skills first?"
Looking Ahead: The Personal AI Revolution
The future Udemy envisions is one where everyone has their own AI assistant, tailored to their role and needs. They're using an enterprise solution called Toqan to enable this transformation while maintaining data security.
"We use Toqan to help everyone create their own AI assistant," Fascenda explained. "The great thing about Toqan is it's within our platform, within our own company instance, so there are certain levels of information... that stays all within our own company walls, and it doesn't go out to feed the broader kind of AI machine."
This approach – with clear guardrails around AI use – has been crucial for adoption. As other participants noted during our discussion, clarity around what's permissible doesn't stifle creativity but rather enables it by removing uncertainty.
The changes underway at Udemy offers a blueprint for how organizations can navigate the AI transformation – not by replacing people, but by reimagining how we work, learn, and grow together. The path forward isn't about substituting humans with technology, but rather creating a new partnership where both can thrive.
"I always tell my team, 'I want you to be at Udemy, but no matter where you go, you're going to need these skills,'" Fascenda concluded. "You're going to need to know how to use AI, feel comfortable with it, and adopt it. That is going to help you no matter where you are in your career, no matter where you're working."
In a world where the only constant is change, that might be the most valuable skill of all.
How do you see the shift to skills-based organizations and generative AI playing out in your organization?
Show Notes
First off, if you’ve made it this far thank you! Brevity isn’t my strong suit. Two quick notes:
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I’m all for hiring within as long as you’re building skills. I worked in higher ed, and they did it for years. But it got so insular and stifling they eventually pivoted and primarily hired externally, which created a whole new mess.
Hope you're having an amazing week Brian 😊
I used gen AI for smallish tech docs and drawing once. Definitely saved some of my time. But, using it needs some time to become a habit.
Then my company announced to double check whether we really need the latest LLM from open AI, as it is too costly. -- Hello?!
Those who hesitate exploiting AI will first lose money for chat bot licenses, before losing business.