From Learning To Measurable Enablement in the Age of AI with Rob Rosenthal, Udemy Business

The Future of Learning: Turning Training into Performance with Rob Rosenthal, President of Udemy Business

The ground is shifting under every team — and the biggest winners are the ones treating learning not as a checkbox, but as a performance system that fuels growth, agility, and innovation.

In this in-depth episode of the HRchat Podcast, host Bill Banham sits down with Rob Rosenthal, President of Udemy Business, to explore how learning and development is being redefined in an era shaped by AI, hybrid work, and rapid skills transformation.

Together, Bill and Rob unpack how AI, executive sponsorship, and measurable enablement can dramatically shorten ramp times, sharpen skills, and deliver business outcomes that leaders can trust. Rob shares what he’s seeing across industries and regions: a growing expectation for L&D to partner directly with technical teams to lead AI readiness while also proving ROI to the C-suite.

Listeners will discover a practical framework for building what Rob calls a “skills operating system” — one that starts with clear assessments and gap discovery, moves through curated learning paths, and lands on deliberate practice powered by AI. Rob explains how AI-based role play and virtual coaching can help new skills take hold faster, and how Udemy implemented this internally to reduce new-hire ramp time by 30% for account executives through structured enablement, not just new tools.

The conversation also explores what skills truly outlast the hype. Rob highlights the continued importance of communication, change management, resilience, and leadership, especially as automation accelerates and teams face constant reinvention. 

Finally, Rob describes how private LLM integrations can deliver targeted, role-specific content at the exact moment of need — whether an engineer is debugging code or a manager is preparing for a tough conversation — turning learning from an occasional event into an everyday habit.

Chapters

• 0:00 Setting The Stage: AI And L&D
• 2:52 Rob’s Path And Udemy’s Mission
• 3:52 Global Event Insights: AI Frontlines
• 4:42 The New Mandate For L&D
• 6:16 From Learning To Workforce Performance
• 7:32 Breaking Barriers With Executive Sponsorship
• 9:02 Measuring ROI: Assessments And Outcomes
• 11:26 Future Skills Beyond AI Hype
• 12:46 Trends: Skill To Fill And Faster Ramps
• 15:40 The Skills Operating System Explained
• 18:22 Human In The Loop And AI Safety
• 19:56 Learning In The Flow Of Work
• 22:18 Connect With Rob And Udemy
• 23:30 Closing And Subscription Reminder

Transcript

SPEAKER_00: 0:02

Welcome to the HR Chat Show, one of the world's most downloaded and shared podcasts designed for HR pros, talent execs, tech enthusiasts, and business leaders. For hundreds more episodes and what's new in the world of work, subscribe to the show, follow us on social media, and visit hrgazette.com.

SPEAKER_03: 0:25

Hello and thanks for tuning in to this episode of the HR Chat Podcast. I'm your host today, Bill Bannham, and in this episode, we're going to dive into one of the biggest shifts shaping the modern workplace. How learning is being redefined in an age of AI, hybrid work, and constant skills disruption. Upskilling isn't just a nice to have anymore, it's a business critical. To help us unpack how organizations can stay ahead, I'm thrilled to be joined today by Rob Rossenthal, president over at Udemy Business. Rob stepped into the role last year after serving as chief revenue officer, and he brings over 25 years of experience driving global growth and transformation at companies like Bloomreach, Adobe, and SAP. Rob spent his career at the intersection of tech learning and performance, helping teams adapt faster and leaders make smarter, data-driven decisions about talent development. Listen as we explore how learning is evolving, what's next for LD in the world of AI, and how Udemy is helping thousands of organizations turn learning into a true growth engine. Rob, how are you doing? Welcome to the show today.

SPEAKER_01: 1:42

Thanks, Bill. Doing great. Really looking forward to our conversation.

SPEAKER_03: 1:47

Me too, me too. So beyond the reintroduction just a moment ago, maybe you can take a minute or two, please, Rob, and introduce yourself to our listeners and tell them also about the mission of Udemy.

SPEAKER_01: 1:59

Yeah, so uh based in Denver, Colorado, uh my my career has been on uh transformation of one flavor or another. And uh in most cases that's meant um digital transformation and tech uh companies like Adobe and SAP. And this is the first time that I've really been on the people side of the business uh and learning and enablement. And uh I'll just say I I kind of knew we weren't doing a great job as uh tech providers on the enablement side of the equation. Now that I am on this side, uh I can confirm that we really haven't been doing a great job. And it's it's just such a big opportunity. So I'm I'm thrilled to be at Udemy and uh helping to helping to transform people, not tech.

SPEAKER_03: 2:48

Okay, we've come to the right place because we love talking about people and people processes. So Udemy hosted the Forward London event uh last week as we record this in the middle of November 2025. Tell me about the event series because it's not just in London, is it? It's all over the world. Uh, and some of the the highlights from the London edition for you.

SPEAKER_01: 3:08

Yeah, the forward event is really important to us. We know that um, you know, people like to come together and and uh trade best practices and learning people in particular, it's it's I've really observed how they like to come together. And uh we we did just that uh last week. It was an amazing event, it was uh quite well attended, much larger than the prior year, which we held in the Gherkin. We we outgrew the Gherkin and uh we had several hundred people. And I think the um everyone uh of course, of course, everyone's talking about AI, right? And uh the the buzz in the room really was um, you know, okay, we've been through the first wave to try an AI enablement. How'd that go? Where's this thing going? And what does it mean uh for the learning and development professional or even the the head of people? What where's this, you know, what what are the implications? So we are doing this all over the world, and we are quite a global company. 60% of our revenue comes from outside the US. So it's really important to get out there and see what these themes are all over the world. I can I can confirm that you know it's a similar story uh in different regions where people are wrestling with the same thing. They might be by industry a little um more advanced or or lagging, but it's the same conversation.

SPEAKER_02: 4:25

Thanks for listening to this episode of the HR Chat Podcast. If you enjoy the audio content we produce, you'll love our articles on the HR Gazette. Learn more at hrgazette.com. And now back to the show.

SPEAKER_03: 4:42

Okay, so we are about two minutes into this particular episode of the HR Track Show listeners, and already we are talking about AI. You can't get away from AI, and let's talk about it even more now. Uh, I'd I'd love to get your feelings, Rob, you in terms of your experience. How have you seen the role of learning and development evolve within organizations over the past few years, specifically in the context of ways that AI has impacted it?

SPEAKER_01: 5:08

Well, well, given that my tenure here is uh you know not even quite two years, I can tell you it has changed a lot since I started at Udemy. And uh the the key change is uh there's a spotlight on LND right now. And that spotlight is uh this the CEO and the board understand that uh LND can be quite strategic, and and they have been given this mandate to enable the team on AI, typically a dual mandate. Uh I'm experiencing it's not just LND, but they have another stakeholder. It could be the CTO or chief AI officer or whatever it is, and this is in the larger companies, the enterprise. So LD has to has no choice but to get really comfortable with what the business outcomes are of this learning and enablement that they're doing. And um that that's where I think the the biggest challenge is is to prove the business value. And uh it's a org-wide challenge in the topic of AI, but L and D has to has to really um help help everyone see the value.

SPEAKER_03: 6:16

We'll talk about it a bit more in my next question for you, but um uh in a when I'm wearing another hat, I'm on the board of a of an L and D uh network of about 500 L and D professionals here in the UK, Rob. Uh and uh I frequently hear from them that uh it shouldn't be HR taking their case to the top table, it should be LD professionals. Just want to get your take on that.

SPEAKER_01: 6:40

Yeah, the uh it's how you look at learning um in general, right? So I completely agree with it. And uh I actually am not a big fan of the word learning. Uh learning, so it's in the title, but I don't like the word. Uh it's like, you know, carrots, it's vegetables, it's nice, but um it can be ignored. And uh we're in an era now where that's not the case, cannot be ignored. So I actually think the LD person, I think Udemy uh itself, we're we're really in the business of enabling the workforce. Um, so it's workforce readiness and ultimately workforce performance. So I don't see L and D as LD, I see it as workforce performance. And if the the LD stakeholders change their title and start lining up against workforce performance, they'll they'll uh I think that that's where this is all going.

SPEAKER_03: 7:32

What are some of the biggest barriers the companies face when trying to create a strong learning culture? And and how can how can how can HR leaders help to overcome them?

SPEAKER_01: 7:42

Yeah, Bill, it's similar to what I just said prior, which is if it's about learning and it's considered a vegetable, the the barrier is no one's gonna do it because it's it's not as clear what the benefit is, and there's no cost of inaction. If I don't eat my carrots, nothing bad happens, right? So the the reality though is um the it needs exec sponsorship. So I I would change the word of learning to enablement. Enablement is more of a business term, and uh enablement has real ROI, real outcomes. I uh the C-suite must get involved. If any of this stuff is really going to matter, uh the C-suite has to help uh push. It has to be a top priority for the company. So um I but I do believe that the majority of LD professionals out there are being asked right now by the C-suite to go figure out AI and enable everyone on it. LD has to ask in return, great, we'll do that, but uh you have to sign up for exec sponsorship promotion, and you actually have to be the first one to go through the program. And uh that that that will overcome this obstacle of inertia. That's the obstacle.

SPEAKER_03: 8:55

Okay, so you've just addressed the why. But what about the how, Rob? How can organizations better measure that ROI or business impact of their of their LD, their engagement initiatives? Um what are some what are some approaches there?

SPEAKER_01: 9:11

Yeah, so this has always been the hardest part uh is measuring uh the ROI and the business outcomes. There's no one way to do it, so it's it's multi-flavor, multi-threaded. Uh engagement is part of it. So I do often see in the office of a chief people officer, often they'll bring us in because some employee survey showed that engagement was off. They want to invest in their people. Uh, investing in something like Udemy is a good way to do that. So you can do a pre and post-engagement, that's just part of it. Um, uh we like to look at assessments. Uh, and let's take AI as the relevant example. Uh, let's do an assessment uh on everyone uh pre-enablement. Uh let's run the enablement and then let's do a post-assessment uh and use you know different tools and techniques. We have assessment capabilities, and there are other ways to do it as well. But let's let's show what what skills were gained and then you know how can we quantify a business value to those skills. In many of our um customer bases, I'll give you a real easy one in professional services, which is an industry we serve, it's a big chunk of our customer base, it's a very clear ROI. Because if someone has gained a skill, then they're then uh more valuable to their end customer. They can bill more per hour or they can fill a job that goes unfilled. So the this um the ROI is black and white, but it's not always that clean. Uh often there are gray areas. We actually have invested in resources called value engineers that we we uh provide. We deploy these value engineers to our customers to help them map out the ROI because it is a bit of a consulting project, uh, and then ultimately be able to articulate and defend the ROI to the C-suite and the board. So that that's how um how important it is to us, and we're right in the boat with our LND and people stakeholders.

SPEAKER_03: 11:06

Rob, we are living in a world where AI is rapidly replacing us or augmenting us and uh making us think about new ways to work. Uh as you as you look ahead from your perspective, which skills, technical or otherwise, are most critical for employees to thrive in in the future workplace?

SPEAKER_01: 11:26

Yeah, I uh I do have a strong point of view. I have a personal point of view, but also what we see in the data. Uh obviously, we can see what what skills are are are um are trending and peaking right now. So uh take AI aside, right? AI can be quite noisy. There are some things that will always be needed, no matter the AI flavor of choice or whatever the wave is 10 years from now. Things like communication skills, things like uh change management, um, things like dealing with adversity. Uh, these are these are critical. The the younger generation really values communication skills right now. So the younger generation entering the workforce, uh, and we we have to serve them. Um I personally am big on leadership skills. I also think um uh as crazy as this sounds, uh writing skills and even handwriting capability uh is important. So um, because you have to go the other way from AI to be relevant as well and stand out and differentiate. You know, what what can what cannot chat GPT not replace? A handwritten note is one example. So uh that's an example I've I've seen in my network that I completely agree with. Uh we should lean into the things that um aren't AI and develop those skills to say about stay balanced.

SPEAKER_03: 12:46

So Udemy works with thousands of organizations around the world. Uh you guys are a pretty well-known brand. Uh, what are some of the emerging trends that you're seeing in how global companies are approaching skills development and continuous learning? Any particular use cases that you'd like to highlight? You mentioned professional services as a sector earlier, but you know, are there are there some particular use cases that you can point to?

SPEAKER_01: 13:11

Uh yeah, in in um professional services, but others as well, it's uh it's it's how do you ramp uh how do you ramp an employee quickly to meet a need? So in professional services, um we've heard the term skill to fill, and uh it's exactly this. How do you um quickly enable a skill to go fill a role? We actually eat our own chocolate, drink our own champagne at Udemy. I do run a global go-to-market function. Uh, sales enablement is critical. So we use Udemy, both our platform, our course content, uh, our instructors. We hired one of our instructors to help enable our folks. We use things like AI role play and assessments, all things we provide, to ramp a newly hired sales rep to be more productive faster. We've reduced the amount of time it takes in the last year. We've reduced by 30% the amount of time it takes for an AE account executive to become productive. In the future, you'll see us doing more and more of this line of business, truly enablement, uh, you know, not just learning, to have real tangible outcomes like 30% uh faster time to be productive. That's um that's where our focus is right now. It's a trend I'm seeing everywhere. So it's uh, you know, how do we move into the line of business? Uh it is interesting. LD, while in a big organization, yes, there might be a chief learning officer and it's centralized. There's also uh learning in every line of business within the big organization. And uh they have different names. Some of them are enablement, some of them are learning, some of them are transformation, but uh every everyone's after the same goal. It is how do I get uh a quick win with ROI that's quite clear and measurable, like I just articulated that we have. Uh my board wants to know how am I ramping our reps? Uh well, we have a program and we'll share it with our customers uh and our our partners and other stakeholders. Here's how we do it, and we'd like to learn from you and and build enablement with you together.

SPEAKER_03: 15:20

Okay, so that 30% that's that's pretty impressive. How much of that is uh improved learning techniques and training techniques? And how much of it is is is improved technology that's now available to automate so many of the sales-related processes that that were more manual only a couple of years ago?

SPEAKER_01: 15:40

It's it's mostly not technology. Uh, there is some tech in it though that I'll I will talk about, but it's mostly uh having a um a system for learning. So we we actually look at it as a skills operating system. It starts with discovery of uh which what skills, you know. Hey, we for example, um I need someone to be a really good consultative seller, or they need to really understand how to do value-based engagement. So, where are they today? Let's do an assess assessment. Where are the gaps? What how can we um partner with this uh employee to fill those gaps? So we call that skills discovery and then skills acquisition, right? Uh, we we provide the learning paths. They're uh not just online, some of it's in person, some of it's cohort. And uh, how do we you know deliver the training? So you get you acquire the skill, and then the skills uh the term in in our industry is skills mastery, but really it's just practice. How do we practice the skills? That's where the tech comes in. So things like AI role play, I can tell you these this is not this is pretty new to the scene. Uh AI coaching, AI role play. Uh look, a year and a half ago, you would take an online course, you might learn a few things and you apply it in, you know, while you while you're in the flow of work, you can apply a learning. Um, however, now that you have AI-based role play and you can custom design a role play for a specific use case. For example, um, I'm telling our story to a new client and uh I want to deliver uh kind of the the gen one for you know level one presentation. I want to make be sure I ask the right questions in the right order. Well, uh you can program the AI roleplay or the AI coach to to to really do this and be the sounding board for for the rep or the employee, and it really does stick. And if you get it wrong, you know, they'll let you know and uh and and reframe it and ask you to to try it a different way and maybe give you some tips. So this interactive, voice-based, right? You're not it's not hands-on keyboard, you're talking to the role play. That makes a difference. And uh it there's the safety of doing it uh by in your own contained environment. There's no embarrassment factor. This kind of thing is really changing uh how learning happens. And uh, you know, over time this will become more of a more of a tutor to help you teach the skill, be sitting on your shoulder, and uh and really helping you practice and develop the skills. So that that's what we're seeing that's different now. It's quite different than when I started, the tech didn't even exist.

SPEAKER_03: 18:21

I I wonder what where does where does the HR department fit in with that in in terms of ensuring that uh with the example that you just used there in terms of the AI agent, um ensuring that there's no inherent biases, making sure that those assessments are correct and valid. How can we ensure there's still a human element, which is a concern, I think, for a lot of HR leaders? How can we make sure that the human touch is still in the right places?

SPEAKER_01: 18:50

It's such a good question, Bill. We recently had an exec advisory council. We got some of our key customers together that are LD professionals from around the world and around industries. And they saw, they said the number one thing is human in the loop. And uh so they they had a couple examples, but they would like us to help them with cohort-based education uh and make sure that there's a human facilitating uh AI safety, I hear all the time. So it's not just, hey, can you give me some AI enablement? No, it's it's you know, are we doing this in a way that um uh is thoughtful, is uh uh compliant with rules and regulations, or what they're gonna be? Can we get in front of this? So just what like you say, Bill, very top of mind. Human in the loop is a big, big deal.

SPEAKER_03: 19:42

Rob, we're flying through our questions for you today, just two more. Uh as you look ahead to 2026 and beyond, what's next for Udemy business and uh what are your priorities to helping organizations stay competitive through learning?

SPEAKER_01: 19:57

Yeah, look, we're um we're innovating like crazy right now. We've uh been spending a lot of money on the on uh new new technology. So we've taken uh the AI toolkit and the techniques and applied it to everything we do. What that means is this concept that we've all we've all heard of learning and the flow of work in 2026, it really does show up uh in a real way. And it's a personalized learning, bite-sized learning. I'll give you an example that we're really proud of. We were the first in in our market to ship um MCP, model context protocol integration. It's a fancy way of saying that we can work with any organization's um uh AI strategy if they if they're using their own LLM uh to help their employees learn. Well, uh that LLM can talk directly to Udemy to help uh show up in a in a you know in a in a compact way. When someone's stuck, uh, you know, maybe I'm uh trying to write some code and uh I need some help and I use my own LLM within the org, it can go talk to Udemy, find the relevant um area to surface and present it back to the employee, and they can solve that problem on the spot. Or if someone needs, you know, I'm a I'm a generalist, I'm not a technologist, and I'm gonna need to have a tough conversation with an employee. I can ask my own LLM within the company, uh, you know, help me figure this out, and it will it will maybe ask a question or two and go go ping you to me and bring you that knowledge in the flow of work and see if it helped. So this kind of uh interactivity, uh leveraging AI tools will will be huge uh next year. So I I think this um the pace of change is is crazy right now. Uh all we can do is keep up with the the integration to the best techniques, that's what we're doing, and making sure that the the learning in the flow of work shows up so that you use it on a daily basis. It should be like a fitness routine, it's not an occasional learning, right? It's um it's not learning by chance, it's being ready to learn at all times and then practicing it daily in the flow of work. That's enablement. That's that's that's when you get the business outcome. It's no longer a vegetable.

SPEAKER_03: 22:13

Okay, and just finally for today, Rob, how can our listeners connect with you? Is that LinkedIn? Do you want to share your email address? Are you super cool and all over the socials? And of course, how can folks learn more about Udemy?

SPEAKER_01: 22:26

Yeah, I'm easy to find on uh LinkedIn. Uh just look up Rob Rosenthal plus plus Udemy, you'll find me. Uh, that is a great way to reach out to me directly, either follow me or connect with me. And uh I do I do check my uh LinkedIn messaging, have found uh many customers actually uh interacting through that channel. So that's the that's the best way. And Bill, what was your second question? How can folks learn more about Udemy? Oh, and of course Udemy is uh we do have uh quite a following on LinkedIn for uh Udemy itself as a brand, but also Udemy for business. So we we a third of our business is is the marketplace, which is business to consumer, and two-thirds is Udemy Business. Um, we have both flavors on LinkedIn, or you can go to udemy.com.

SPEAKER_03: 23:13

Perfect. Well that just leads me to say for today, Rob, this is the first time we've had a chat. I'm hoping it's not the last, but for today, thank you very much for being my guest.

SPEAKER_01: 23:23

Thank you, Bill. My pleasure, and uh look forward to uh staying in touch with you.

SPEAKER_00: 23:31

Thanks for listening to the HR Chat Show. If you enjoyed this episode, why not subscribe and listen to some of the hundreds of episodes published by HR Gazette? And remember, for what's new in the world of work, subscribe to the show, follow us on social media, and visit hrgazette.com.