Welcome to View from the Top—a series where I sit down with CMOs and marketing leaders to explore the future of our industry. Marketing has always moved fast, but with the acceleration of AI, evolving privacy expectations, and shifting consumer behaviors, we’re in a moment of unprecedented transformation. My goal with these conversations is to uncover how top leaders are navigating this new terrain—and share insights we can all apply.

For the very first installment, I had the pleasure of speaking with Kelly Waldher, CMO of Zendesk. Kelly has held marketing leadership roles at some of the most iconic tech brands, and I was eager to learn how he’s approaching the AI revolution, tackling the privacy paradox, and guiding his team through this era of rapid change.

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Roli: First off, Kelly, thank you for being our inaugural guest! You’ve built an impressive marketing career at some of the most influential tech companies. What key moments or decisions have shaped your path to becoming CMO of Zendesk—and how have they influenced how you see the future of marketing?

Kelly: I’ve had the good fortune of learning from a number of incredible marketing leaders over the years and have tried to absorb and incorporate best practices into my own approach. One of the biggest lessons has been staying curious and open to doing things differently, especially in the face of disruption. The shift from software to cloud, PC-centric to mobile-first, and more recently, the dramatic rise of generative AI—each of these has been a key inflection point during my career. Maintaining a ‘learn-it-all’ vs. ‘know-it-all’ mindset has been the biggest takeaway, and it continues to guide how I think about the future of marketing. More specifically in the case of AI, I’ve found the Marketing AI Institute to be a great resource as well as Lex Fridman’s podcast, which routinely has AI expert guest speakers.

Roli: That mindset of staying curious really resonates—especially now, with how quickly AI is changing the game. Let’s dig into that a bit. How is Zendesk leveraging AI in your marketing efforts today? And what do you think are the biggest opportunities—or hurdles—CMOs are facing when it comes to adopting AI?

Kelly: At Zendesk, we’ve taken a very proactive and inquisitive approach to leveraging AI in our marketing strategy. As new AI marketing tools (and companies) emerged, we built a three-pronged approach to testing and adoption. First, we formed an internal cross-functional team to act as our AI marketing steering committee. Second, this team conducted a series of tool assessments to determine which AI solutions we should experiment with. And third, we piloted these tools while establishing clear metrics to measure effectiveness. Based on those results, we either fully adopt a tool or replace it with another for further testing.

Three specific use cases where we’ve found early successes include message testing before we publish a press release, content creation to improve our SEO results, and competitive teardowns to enhance our battlecards and develop more effective depositioning. There are so many possibilities, so my advice to other CMOs is to enlist a few of your leaders who have a passion for AI and encourage them each to develop hypotheses, test, learn and iterate with their teams to find the value.

Roli: I love that intentional, test-and-learn approach. With so many tools popping up, it’s smart to have a real framework for experimentation. Now, if you had to make one bold prediction about the future of marketing in this AI-powered, privacy-first era—what would it be?

Kelly: I believe that generative AI will be on par with, if not a bigger disruptor to marketing than the advent of search engines. Just like search engines created the need for digital marketing expertise, AI will reshape how we create content, optimize campaigns, and drive engagement. For marketers who are curious and open to adapting their approaches, AI tools will lead to higher-quality work, greater efficiency, and increased business impact—making for a more rewarding career in marketing.

Roli: That comparison to search engines is so compelling—AI really is that level of game-changer. Of course, one of the trickiest parts of all this is balancing personalization with privacy. As regulations evolve and consumer expectations shift, how do you see marketers navigating that line?

Kelly: As marketers, we’ve been navigating this balance for a while, whether through GDPR, CPRA, or other privacy regulations. Generative AI, and specifically large language models trained on both public and private data, will only amplify this challenge. Interestingly, while AI is creating new opportunities for personalization, it’s also exposing new risks. The upside? AI will likely play a major role in ensuring privacy safeguards and regulatory compliance are met, helping brands find that equilibrium between relevance and responsibility.

At Zendesk, we have a rigorous security and compliance review process, so every AI tool that we consider goes through an in-depth assessment before it’s deployed into our environment. While this adds a few extra steps and time to the schedule, this helps us appropriately balance the use of AI in our marketing activities with regulatory security and compliance safeguards.

Roli: It’s such a paradox—AI is both the risk and the remedy when it comes to privacy. And with so much transformation underway, the pressure on CMOs to prove marketing’s impact is only growing. What strategies or tools are you leaning on to connect marketing efforts to real business results?

Kelly: I’m a huge believer in data-driven marketing. That doesn’t mean sacrificing great storytelling, compelling messaging, or creative innovation—but it does mean that measuring value should be built into your strategy from the start. We closely track key metrics like pipeline-to-spend and return on ad spend, ensuring we’re tying marketing efforts back to business impact.  For me personally, the two metrics that I look at every day are pipeline creation pacing for our sales assisted segments and new customer acquisition for our self-service business.

As we discussed earlier, AI is making it easier than ever to both measure impact and increase efficiency. In this AI era, marketers actually have a real opportunity to do significantly more with less. As I look out over the horizon, I see future CMOs continuing to rise up through the various sub marketing functions (i.e. Demand Gen, Product Marketing, Brand Marketing, etc.), but in every case, I think they will be deeply skilled in leveraging AI to deliver high impact results, with greater throughput, at a lower cost.

Roli: Yes to that—impact over activity, always. And it’s exciting to think about how AI can help us be both more effective and more creative. OK, last question—let’s have some fun with it. If AI could take one annoying task off your plate (work or life), what would it be?

Kelly: This is an easy one: attending meetings on my behalf that have limited value. I think we all struggle with too many meetings, so getting that time back to focus on our craft as marketers would be exciting.

Roli: I think every marketer reading this just nodded in agreement! Kelly, this has been such a great conversation—thank you for sharing your insights. It’s clear that AI and privacy are reshaping the marketing landscape, but as you said, the best marketers will be the ones who stay curious and embrace change. Excited to see how Zendesk continues to innovate in this space!

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Thanks again to Kelly for sharing his thoughts on the evolving marketing landscape, especially around AI and privacy.

Stay tuned for more "View from the Top" interviews coming up every month. You can check them out right here on my LinkedIn profile. I’ll be diving into what the best and brightest in the industry are doing to shape the future of marketing. See you next time!