HRTech Interview with Rob Rosenthal, Chief Revenue Officer at Udemy

Rob Rosenthal, Chief Revenue Officer at Udemy chats about the core sales and revenue tactics that can boost growth for HRTechs in this Q&A:

Hi Rob, tell us about yourself and more about your revenue and sales journey in the B2B SaaS market.

I’m currently based in Denver, Colorado, and I have more than 25 years of experience in the software industry with a diverse background across go-to-market (GTM) roles.

I also have extensive experience building and leading large-scale revenue and sales functions at both publicly traded companies like Adobe and SAP, as well as high-growth venture-funded SaaS companies like Bloomreach, where I was most recently Chief Revenue Officer (CRO).

As Udemy’s CRO, my focus is on driving the growth and retention of more than 16,000 Udemy Business customers worldwide. From customer success to GTM strategy, I oversee all revenue-related functions to ensure our customers and employees are set up for success in serving more than 70 million learners globally.

What about today’s state of sales and revenue generation needs an overhaul in B2B SaaS?

There is a huge focus on product-led growth (PLG) and “selling product-forward,” where we align customer needs with business goals.  

Although today’s buyers are often technically savvy and may want immediate access to the product, depending on the segment, a compelling value proposition for the overall business remains essential.

The business value must be clear, durable, and sustainable for customers. PLG-focused SaaS companies that do not establish substantial business value for customers can witness a significant drop in net dollar retention.

Read More on Hrtech : HRTech Interview with Charlotte Dales, Co-founder and CEO at Inclusively

Take us through some of your revenue tactics and strategies as well as the revtech/salestech that helps power it all?

Every GTM strategy within an organization requires a framework or operating system as a foundation. From my experience working with key principles of a scaled framework, I have adopted best practices from other organizations in this role. 

Each business is unique; however, it is critical to apply these fundamental learnings and then adjust your strategy accordingly. An effective framework should be easy to comprehend and can ideally provide visibility for the next few quarters, ensure high forecasting accuracy and predictability, facilitate regular collaboration across go-to-market functions and other stakeholders, and include mechanisms for evaluating and benchmarking performance across functions. 

The tech stack powering GTM is ever-evolving, particularly with the proliferation of AI tools available. A combination of a CRM tool and a system designed to optimize the outputs of the CRM can together help run the business efficiently.

Udemy itself is an outstanding platform that supports enablement by providing insights such as leadership training for first-time leaders. I’m greatly looking forward to leveraging all that Udemy has to offer to continually upskill the GTM teams.

Coming back to your new role as Udemy’s CRO: take us through some of the near-term plans and vision you have.

While I am in the midst of outlining my vision and long-term strategy for Udemy Business, there are clear trends I will be monitoring to identify how we can maximize our opportunities.

There is an urgent need for global businesses to learn how to take advantage of generative AI for their strategic benefit and progress. Organizations that can learn and adapt swiftly will rapidly outpace their competitors, and Udemy is supporting organizations of all sizes to accomplish this with speed and high engagement at scale for operational efficiency. 

Another key opportunity is for organizations to consolidate spending across functions such as learning and development. This can be achieved by leveraging a comprehensive generative AI-powered platform like Udemy for upskilling and reskilling the workforce at scale. 

What does it take to drive revenue and market impact in the HRTech space: what should HRTech CROs keep in mind?

In today’s competitive market, your product or service must deliver a clear and differentiated business value. If this value isn’t immediately apparent, it’s crucial to question what steps you and your team are taking to address this gap. 

When it comes to HR technology, consider what it would take to transform your solution from merely a ‘nice-to-have’ into a ‘must-have.’ Understanding the cost of inaction is also important. 

These are vital themes to explore with customers, partners, and go-to-market teams to ensure your solution stands out and meets critical business needs.

Five sales/revenue practices that you feel everyone in sales should follow on a daily basis before we wrap up?

First and foremost, prioritize customer outreach and feedback. Leaders can sometimes lose sight of the most basic principle which is to maintain regular contact with customers and gain a deep understanding of their challenges and priorities. To achieve this, daily outreach across all levels of the GTM team, including the CRO, is essential. 

A similar approach should be taken with partners. Maintaining close contact with strategic partners and treating them as an extension of your team will keep you apprised on the market and enhance your GTM execution.

Thirdly, prospecting is essential. No B2B sale occurs without effective prospecting and lead development. Every individual contributor should be prospecting daily, working closely with their Business Development teams and leadership, all the way up to the CRO, to actively support these efforts. Personally, I leverage my network and assist with outreach, ensuring my team knows they can always count on me.

This may be unconventional advice in sales, but incorporating physical activity into your daily life is extremely beneficial. For me, no day is complete without some form of exercise, preferably outdoors. There is a proven connection between the brain and the body. If you want to be at the top of your game in sales, I recommend exercise.

Last but not least, never stop learning. Whether you’re upskilling in your professional role or practicing a new hobby, spend time regularly to learn new skills. Today, we have opportunities to learn through different formats depending on your learning style – from listening to a podcast (pair that with working out and you’re golden!) to watching a video. There are several soft skills that continue to emerge in communications and leadership that can be vital for sales professionals to master. Rather than scrolling through social media, visit the Udemy platform to pick from more than 220,000 courses and upskill today.

Catch more HRTech Insights: HRTech Interview with Jonathan Leaf, CRO at BambooHR

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As Chief Revenue Officer of Udemy, Rob Rosenthal is responsible for growing and retaining more than 16,000 Udemy Business customers across 150 countries. This team includes Udemy Business Sales, New Ventures, Customer Success, Partnerships, Go-To-Market Strategy and Ops, Leadership Academy, and Global Customer Support. Rob also leads the Denver office which is a regional hub for Udemy.

Rob joined Udemy in 2024 as a software executive with over 25 years of sales and leadership experience in e-commerce, marketing, CRM, and other digital platforms. Rob’s earlier roles include Chief Revenue Officer at Bloomreach, a leader in e-commerce personalization and marketing technology, where he led a team that tripled growth at this late-stage privately held company over a four-year period. Prior to Bloomreach, Rob held senior GTM roles at Adobe where he led Americas for the high growth Corporate segment, and at SAP where he led the Americas for the Customer Engagement & Commerce division.  

Rob holds a bachelor’s degree in Organizational Communications from Arizona State University in Tempe, Arizona, and resides in Denver, CO with his wife and two children.


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