Udemy’s Rob Rosenthal on the evolving role of a CRO

What skills make an exceptional CRO?

In this episode of Reveal, host Dana Feldman sits down with Rob Rosenthal, Chief Revenue Officer at Udemy, to uncover the core skills and responsibilities expected of a great CRO. With a proven track record at companies like Adobe, SAP, and Bloomreach, Rob brings a wealth of knowledge to the table.

Throughout the conversation, Rob shares his insights on staying customer-focused, building strong cross-functional alignment, and learning consistently throughout your career. Mastering these skills is essential for anyone striving to become a top-tier CRO.

Rob Rosenthal:
For sure, you’re going to get a lot wrong, and you have to be really comfortable with that. And you’re going to get criticized. You have to be comfortable with that, too. You got to grow a thick skin and just, just roll with it. But you have to experience it to really grow from it. And I’ve definitely experienced that. I’ve made plenty of mistakes. I’ll make plenty more.

Dana Feldman:
What do the world’s best CROs have in their playbooks? This is the place to find out. This is Reveal, the Revenue Intelligence Podcast. I’m your host, Dana Feldman. Hi, I’m Dana Feldman. And this is Reveal, the Revenue Intelligence Podcast. Each episode we’re focused on helping you build the ultimate CRO playbook. And we promise to give you access to the most influential people and revenue leaders at the world’s top companies. And I’m going to deliver on that promise today.

Dana Feldman:
And I am very delighted to be joined by my guest, Rob Rosenthal. Rob is currently serving as a CRO at Udemy and has over 25 years of experience in the software industry. Before joining Udemy this year, he held positions at very admirable companies like Adobe, SAP, and Bloomreach. And at Bloomreach, Rob played a key role in tripling the company’s revenue from 2020 to 2024. While at Adobe, he helped scale the America’s enterprise business from 1 billion to 2 billion and significantly contributed to transforming the company’s sales strategy. So just an incredible track record of success. His leadership in these roles has positioned him as no doubt an expert in driving revenue growth and expanding global teams and operations. So I’m excited to dive in.

Dana Feldman:
Rob, welcome to the show.

Rob Rosenthal:
Thank you, Dana. Pleasure to be here.

Dana Feldman:
So, Rob, you know, quite the career journey and I would love to maybe start just from the beginning. Will you give the listeners a little bit of an overview of how you got to where you are today?

Rob Rosenthal:
Yeah, I’ve had three arcs of the career. Started carrying a bag for a few software companies and you know, in the late 90s, I was slinging Y2K testing software for a company like Compuware selling to COBOL mainframe programmers. So that definitely dates me. You know, have seen the evolution of on premises large ticket software into SaaS over time. You know, carrying a bag for about 10 years and then got into leadership and did all the trials and tribulations of first line and second line. I know how hard those jobs are. You don’t want to stay there very long because they’re the hardest. Right.

Rob Rosenthal:
You get it on both ends and in terms of the challenges and got into senior leadership around 2010, 11 or so and have worked small companies that got acquired like Hybris was, it was an E commerce platform that was about 150 million in revenue that SAP acquired and ended up running the North America for that unit. Really that was my ticket into large enterprise software and to really see what scale looks like, you know. And I took that to a career at Adobe in senior leadership roles and then CRO at Bloomreach to you know, really practice what you preach and get a chance to try all the go-to-market functions and did that for about four years and after a little career break been at Udemy now for about five months and you know, publicly traded CRO role a little different than the last one and tons of fun.

Dana Feldman:
I love that. I, I have to ask because it’s always an interesting story, but why sales? How did you get into sales in the first place?

Rob Rosenthal:
I’ve been in sales my whole career. I knew in college I was likely to go in sales mainly because you couldn’t make anything happen. Sales, you know, it’s effort, it’s focus. If you work hard, get the on the right stuff, you’re going to have good outcomes. So I’ve always been a bit of a grinder as a mentality and I think sales was really good for that. And the son of a salesperson. My dad was a Levi Strauss sales rep back in the day and he had the gift and I think I learned from osmosis. Just really appreciate the art of sales.

Dana Feldman:
No, I love that story. Well, thank you for sharing that. I’m curious, in all those journeys that you’ve had, what have you learned from past roles that you take to each new role that you step into?

Rob Rosenthal:
Personally, I take each role for the learning opportunity. One fun fact about my career is I’ve never stayed anywhere more than five years. That’s with great intention. So you know, I learn a little bit each place and it goes into the personal playbook and you know, it does shape and form where I go and what I look for. So what I’ve really learned is that over time I do like transformation. I like moving people and organizations from A to B or B to C or wherever phase we’re in. And it’s because I’ve seen a little bit each place and I’ve had great people to learn from at each stop. So it’s not just one thing, it’s every single place, including Udemy. I’m learning.

Dana Feldman:
I love that. So you’re really always thinking in the back of your mind as you’re evaluating opportunities, you know, what am I going to learn from this opportunity? Where is that going to grow me, stretch me, challenge me?

Rob Rosenthal:
Right, that’s exactly right. Because that for me is why I do it. It’s personal growth and helping others grow with great intention. I think about what I’m going to learn over what time period and from whom.

Dana Feldman:
Yeah, well, I don’t think you could have picked a better company if that’s your philosophy to land at than Udemy. Right? For the principle of what you all stand for and who you are. So, as you reflect on your career and these different moves, is there anything that you would have done differently, or was there maybe one really impactful learning, or some might call it a mistake, that maybe others can learn from?

Rob Rosenthal:
You know, early in my career I probably moved too quickly from, maybe I’d set up as an individual contributor. And you learned this, you put in a lot of hard work and you set up a patch, and then if you move off that patch too quickly, someone else is going to really benefit from that. I learned patience, which is kind of ironic because I just told you I’ve never been anywhere more than five years. Learning to be patient when you’re younger in your career is pretty critical. And also, don’t underestimate the power of the brand of working at a larger software company and the opportunity that gives you—not only the brand because it validates your resume, but you learn so much from big software companies.

Rob Rosenthal:
SAP is the best example I can give. When we were acquired into SAP, I was just floored by the amount of talent everywhere I looked. Talk about learning opportunities—it was a well-oiled go-to-market machine, and I was thankful to be there. It would have been great to be there earlier in my career, it probably would have accelerated a lot of my development. So, those are the two things: one, patience, and two, seek out a world-class large company to work for early in your career. It validates you and really helps you prepare for future roles.

Dana Feldman:
Yeah, I agree. And it gives you such an opportunity to see well-implemented frameworks, processes, initiatives, right? That you can then take and bring on if you ever choose to go into more of a build sort of role at a smaller organization. The other thing I often talk about, too, for people early in their careers is that you never want to get into a role where you don’t have the experience that lends itself to you being able to show up credibly but also think through things in the right way. You’ve faced some of it before. If you haven’t given yourself that time to go through those experiences in roles, it creates an incredible amount of stress if you get to a role too quickly as well. That’s kind of been my observation.

Dana Feldman:
I’d love to dive in a little bit more to your leadership philosophy. I know that mentorship has played a really key role in your journey, and I’d love for you to share more with the audience around that, and maybe even how you might be returning the favor today with mentoring.

Rob Rosenthal:
Yeah, it really is true. I mean, the reason I like transformation so much is because not only do you help an organization, but you help individuals achieve their goals. One thing I do in every interview is really try to understand what someone’s motivation is: why they are leaving where they are, why they want to come join us, what is motivating them? Or if I’m new to a team, I really want to understand what everybody’s career aspirations are—where are they trying to go? Because I am always trying to connect the dots between their desires and what we have to offer. It’s like a giant jigsaw puzzle that never ends. There’s nothing better than looking back, maybe after you leave an organization, and hearing from those people over time and getting a thank you. There’s nothing better than that. So, that’s really motivating for me—to help people get to where they want to go. That’s why I do what I do.

Rob Rosenthal:
As for how I do it, there’s no exact formula. It’s about spotting talent and recognizing people who are hungry. I pay close attention when someone clearly differentiates themselves. You know it when you see it—someone who is curious, asking great questions, showing leadership potential. I make time for those people, whether I work with them now or I worked with them 10 years ago. It doesn’t matter.

Dana Feldman:
I heard a little bit about a meeting that maybe you run weekly, that you open up to not just leaders but also individual contributors. Can you share more about that?

Rob Rosenthal:
Yes, I’m not a huge fan of traditional staff meetings. Now, there’s no issue with executive staff meetings—you need those to run a business. But for my own meetings, I’ve never been a big fan of having a team meeting. What I prefer is a meeting with all leaders, no matter where they sit in the organization—all field. It doesn’t even have to be my team; it’s cross-functional. In fact, if anyone in the company wants to join who’s a leader, they can. I don’t care.

Rob Rosenthal:
It’s called the Field Leadership Meeting. It’s brief—a 30-minute weekly check-in, like a standup for leaders. The purpose is two-fold. One is to share: “Here’s the most important thing at my level,” or “Here’s what my team is working on this week.” It’s about communication, and part of it is also intake: “What’s blocking you from getting your job done?” We don’t need to wait a quarter for a QBR to surface issues. Let’s talk about it weekly, throw it out there, and track it. We assign homework, and then we owe you an update the next week. This meeting is also a great opportunity for individual contributors who aspire to leadership to see what’s going on and why decisions are made.

Rob Rosenthal:
The beauty of this meeting is that there are plenty of individual contributors who want to become leaders, and they should come to this meeting. It’s a good opportunity for a manager to bring an individual contributor in, give them a glimpse of what’s going on, what the blockers are, and they get a taste of why certain questions are asked and how to solve those problems. So, it’s a Field Leadership Meeting—it’s a time saver, great for communication, and helps everyone stay aligned.

Rob Rosenthal:
We also use Slack as a follow-up. I don’t use a ton of Slack channels, maybe five that I rely on religiously, and one of them is dedicated to this meeting for tracking action items and progress.

Dana Feldman:
I love that. We’re kind of getting into the topic of your leadership philosophy, so I want to ask more about that. How would others describe your leadership philosophy?

Rob Rosenthal:
You know, I consider myself to be “in the boat” with the field. That’s really important to me. I am customer-facing, partner-facing, and I try to stay relevant. You can’t always be in front of the customer every day; you need to find a balance. But I do try to understand what’s happening and have a commercial mindset regarding what’s really important to drive the business. I have empathy for the field because I’ve grown up in many of those roles. Most importantly, I am focused on what the customer says and what their needs are. It’s not about selling to them—it’s about helping them. Selling is helping, at its core. I try to be relevant and a great partner to the field.

Dana Feldman:
What do you think is one of the hardest lessons in leadership you’ve had in your career?

Rob Rosenthal:
One of the harder lessons is that you are going to get a lot wrong, and you have to be comfortable with that. And you’re going to get criticized. You have to be comfortable with that, too. That’s never going to stop because you’re always going to make mistakes. You’re going to say dumb things. You have to grow a thick skin and just roll with it. You can hear advice like that, but you really have to experience it to grow from it. I’ve definitely experienced that. I’ve made plenty of mistakes, and I’ll make plenty more.

Dana Feldman:
I hear you on the thick skin. That’s one of my top leadership lessons, too—forming that thick skin and being open to critiques from all angles. Is there a specific focus you have with your leaders and your leadership team that has had a high return on investment, or something you implement at any role you step into to help build a strong team?

Rob Rosenthal:
One big focus is on enablement. I’ve been fortunate to work for great leaders who invested in me and my peers. Robby Traube from Adobe really stands out. Here’s a guy who spent time, hired consultants, hired sales trainers, and truly invested in his people. I saw that and thought he’s world-class. I try to do better each year with enablement for all roles, not just my team but the entire field.

Rob Rosenthal:
At Udemy, we have a unique opportunity to practice what we preach—we call it “drinking our own champagne.” We recently hired a facilitator to bring in a value-oriented, value-first selling methodology, which extends beyond sales to include a value-based engagement process. What’s cool is that the person we hired is already an instructor on Udemy. We’re co-creating content with him that will be available to all our customers. We have 16,000 customers in our B2B segment who can also benefit from this.

Dana Feldman:
You mentioned enablement and cross-functional accountability earlier. How do you work with your cross-functional partners to drive results?

Rob Rosenthal:
One important aspect is hiring, upscaling, and promoting people with a cross-functional mindset. Sometimes it takes a while to figure out who these people are when you’re new to an organization. For example, if you want to execute on a target list in a specific vertical, there’s a lot of work that needs to happen: developing use cases, ROI statements, customer references, maybe even product adjustments. You have to align ADRs, revenue operations, and data teams. It’s truly cross-functional and extends beyond just go-to-market efforts.

Rob Rosenthal:
Right now, I’ve identified someone in the field who’s very well-respected to own this process from concept to launch. Once it’s launched, we all own it. But getting it off the ground is challenging, so you need someone who’s a high-output, process-driven systems thinker. Thankfully, I’ve found that person here at Udemy.

Dana Feldman:
Is there a particular communication style or tool you’ve found most effective in driving alignment and results?

Rob Rosenthal:
It’s not necessarily about tools—it’s more about communication style. A huge credit goes to Ursula Kralova, the Chief People Officer at Bloomreach, who brought in trainers to help us understand “5 by 5 communication.” If you want something to stick, you need to communicate it five times through five different channels. Here at Udemy, we’re even talking about “12 by 12” because we’re a larger organization. The concept remains the same: focus on a few vital things, communicate them frequently, and through various mediums. If you do it right, it never ends—it’s a continuous campaign. If you keep changing your priorities every quarter, it’s far less effective.

Dana Feldman:
Your role as a Chief Revenue Officer has evolved quickly. What’s your perspective on the CRO role now, especially given the increasing pressures to drive results?

Rob Rosenthal:
The CRO role can mean so many different things at different companies. I see it as encompassing all customer-facing functions. It’s about aligning go-to-market, customer success, partnerships, support—everything that touches the customer. If a CRO is merely a fancy title for a VP of Sales, that’s fine too, but the real impact comes when you embrace a cross-functional approach. Increasingly, you see this “President/CRO” title, which is about evolving into a general manager mindset.

Rob Rosenthal:
If you are someone who sees across different lines within your company, and you just want to serve the customer, titles don’t matter. A CRO should think like a GM, leading cross-functionally to help customers get the outcomes they’re seeking. That’s how I look at the role—if it’s done right, it’s about serving the customer and aligning all customer-facing functions.

Dana Feldman:
You mentioned before that the role is full of problem-solving. Do you have a process or framework that you apply to solving problems, or can you share something that listeners can take away in terms of how you approach it?

Rob Rosenthal:
Yeah, and I’ll use a specific example here. If you do this right, you can separate yourself from the pack, and that’s helping the product organization stack rank and prioritize where their investments should be made. This is something I learned at Adobe. Product leaders would often ask, “Where should we make our next investments?” I had to provide feedback, but getting the field to respond effectively was tough. It would usually result in a lot of opinions with very few hard facts.

Rob Rosenthal:
So, we developed a program which I’ve iterated on ever since. We call it the “Voice of the Field” here at Udemy. On a quarterly basis, we take stack-ranked feedback from the field to the product teams and put numbers and attribution behind it. The idea is to limit it to the top three most critical needs that the field has to meet our goals. I ask all the leaders to work with their teams to come up with this feedback. The natural owner of this process is the head of pre-sales engineering because they are a good partner between the field and the product team. They tend to be great process people.

Rob Rosenthal:
We just had our first “Voice of the Field” meeting since I joined five months ago. We presented our top three priorities to the product team. Now, we’re reviewing those to see how we did, what commitments were made, and whether we need to adjust any of the priorities. This approach is both qualitative and quantitative—it provides crisp feedback to the product team, leading to better outcomes. At Adobe, we could directly correlate product improvements to customer needs, which resulted in significant revenue. The field came back with specific customer demands, and we used that data to justify investments, which paid off.

Dana Feldman:
This ties into where I wanted to go next. You mentioned that a Chief Revenue Officer should be customer-centric. So, as you look forward 10 years, what do you think are going to be the most disruptive innovations we’ll see for revenue teams?

Rob Rosenthal:
Alright, I want to answer that in two parts. First, there’s the obvious answer—what we can already see coming—and then there’s what won’t change, even 10 or 20 years from now. The clear disruption on the horizon is that the value proposition that many in sales have relied on will change. Are we really going to have people pounding the phones or sending cold emails for much longer? I doubt it. The days of routine sales tasks are already behind us, or nearly so. If your role is about doing repetitive tasks, that’s not going to be needed much longer. Technologies, including your own, are automating routine admin tasks, CRM hygiene, and more.

Rob Rosenthal:
What this means is that revenue teams need to shift focus to what doesn’t change. And those are the fundamental, human-centric skills: listening to the customer, asking the right questions, caring about their needs, doing your homework, and having a strategic approach to where you spend your time. Those things will never go out of style. In the end, sales is about relationships and understanding customer pain points to help solve them. You can’t automate that.

Rob Rosenthal:
At Udemy, I’m really focused on this human aspect of sales. We have 73 million learners on our platform and over 250,000 courses. What’s interesting is that courses on leadership haven’t changed much over the years because the principles of good leadership are timeless. That’s where we want to invest more—helping people develop those skills that are going to remain relevant, no matter how technology evolves.

Dana Feldman:
I love your perspective on that. Now, let’s pivot to artificial intelligence. What are you most curious about with regards to AI and how it’s impacting your space?

Rob Rosenthal:
There are so many different flavors of AI coming out so quickly, and I’m really curious about how much context AI can truly understand. For example, can AI connect the dots between what a Chief Executive Officer or a C-suite executive is trying to achieve and how we can align our engagement to that? Can AI help me upskill my sales team so that they understand what the North Star is for the companies we work with? This way, we can be much more effective in serving our customers.

Rob Rosenthal:
Our customer base often includes Chief People Officers or VPs of Learning, and sometimes they themselves are not fully aligned with their own organization’s broader business goals. I’m really interested in whether AI can help us align better with our customers’ North Stars, ultimately becoming higher quality, strategic partners. I believe it can, and I’m starting to see it, but I’m still exploring how to best harness it.

The Importance of Process Goals and Consistency in Achieving Success

Dana Feldman:
You’ve shared a lot of great knowledge and advice today, Rob. I want to close out by asking: As a revenue leader, what’s the best piece of advice you’ve received along your journey?

Rob Rosenthal:
You know, it’s not just one piece of advice but a whole category of thinking—it’s about process goals. A process goal is something you do consistently every day. For example, if you’re a sales rep, how many executive outreaches did you make today? Maybe your target is five. It doesn’t sound like a lot, but over ten days, that’s 50 outreaches to C-level executives. It’s about showing up with consistency.

Rob Rosenthal:
Everything we’re doing at Udemy right now is about affecting change with process goals. We meet on them weekly at the executive staff level. Personally, I like to ride bikes. I have a process goal of riding 16 miles a day, which takes about an hour. If I miss a day, I owe myself 32 miles the next day. It’s the same idea—consistency in small, daily actions that build up to big results. Having OKRs and high-level goals is great, but if you don’t have process goals, you’re not going to move the needle.

Dana Feldman:
I love that advice—it really hits home for me. Rob, thank you for sharing your insights. This has been an amazing conversation.

Dana Feldman:
To our listeners out there, thank you for joining us on this episode. Be sure to follow Gong on LinkedIn for tactical takeaways from this conversation, including the best plays to add to your playbook. And don’t forget to follow the show so you never miss an episode, especially ones like this.

Rob Rosenthal:
Thank you, Dana. It was fun. I really enjoyed it.

Dana Feldman:
Thanks so much for joining us for this episode. Follow Gong on LinkedIn for tactical takeaways from this conversation and be sure to subscribe to the show so you never miss an episode.