An Interview with the CMOs from Zendesk and Slack
As AI shapes and shifts the business landscape with head-spinning speed, marketing leaders find themselves at the intersection of opportunity and uncertainty. The AI movement continues to surge forward, but the technology’s true potential extends far beyond routine content generation – and few marketers understand this better than Kelly Waldher and Ryan Gavin, two industry veterans who’ve had front-row seats to AI’s evolution.
Waldher, Chief Marketing Officer at Zendesk, brings a unique perspective influenced by leadership roles at Google Workspace, Qualtrics, and Microsoft. His journey from chemical engineer to marketing executive mirrors AI’s own transformation – from theoretical concept to practical business tool. At Zendesk, he’s leading the charge in implementing AI solutions that are revolutionizing customer and employee service operations.
Ryan Gavin’s experience offers an equally compelling lens on AI’s trajectory. As Slack’s CMO, he oversees a platform where AI isn’t just an add-on – it’s becoming the backbone of modern workplace productivity, with many AI apps and agents already deployed across the platform. In addition, Gavin helped establish the AI/ML category at Amazon Web Services during its critical growth phase. He also served as Chief Growth Officer at Convoy, a tech-driven trucking marketplace.
Together, Waldher and Gavin offer insights in moving beyond AI hype to achieve tangible business outcomes. Their insights, drawn from decades of experience, provide a roadmap for marketing leaders navigating the AI revolution.
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How do you define AI in today’s marketing context?
Kelly Waldher: We’ve got machines demonstrating some form of intelligence that we associate oftentimes with human beings. AI’s ability to learn is quite powerful – being able to reason over what it has learned and then solve problems.
Ryan Gavin: Back in my AWS days when machine learning and AI were really starting to ramp up, AI was just hype. It was the thing you talked about when you didn’t know what you were talking about. Now AI is going into reasoning, bringing in creativity. You’re able to suggest actions and take actions.
How can organizations move beyond “AI pilot hell” and implement AI effectively?
Kelly Waldher: I think CEOs have had a generative AI magical moment, and they get it. But here’s the gap: They’re ready to go but they don’t know exactly where this is all going. I think it’s important to start with a finite set of hypotheses. For example, if your goal is to help your AI agents get more productive, be very intentional about the pilots to run. Test and prove it out.
Ryan Gavin: Once you get beyond the basics of AI application, which is really content generation, you have to ask, ‘Where do we have the data that can go and train these systems?’ You have to pick the top three areas based on your business, and choose what you’re trying to get done that makes the most sense.”
What practical applications of AI are you implementing in your marketing operations?
Kelly Waldher: We are big, big users of ChatGPT Enterprise at Zendesk internally. Our Comms team will write a press release, run it through ChatGPT Enterprise and ask it to analyze what messages are coming through. Our creative team is also using Adobe Firefly, which offers a really great set of tools to help generate images and other creative content that we’re using in the brand and in our demand-gen campaigns.
Ryan Gavin: We were able to train Writer AI on our brand and our tone of voice. How do we talk? How do we write? What makes it unique? So now when we are working on a blog, we don’t just get the power of a general LLM, we get something that’s purpose-built for Slack.
How do you address security and governance concerns with AI implementation?
Kelly Waldher: We are gated at least internally at Zendesk. Before we can do a pilot, it has to go through a security and compliance formal review to make sure that we’re not leaking out proprietary data, and that by integrating a new tool we’re not opening up some new security vector.
Ryan Gavin: When you have customer data, when you have personally identifiable information, when you have conversations happening in Slack, those can’t go anywhere. There are lots of machine learning techniques like RAG (retrieval augmented generation) which allows you to tap into the powers of LLM without giving it the data, and without having to train on things like customer data.
How do you think about competitive differentiation in the AI era?
Kelly Waldher: As marketers we need to deeply understand the market we’re in and go really, really deep on identifying customer pain points, and map it back to the company’s current and future durable differentiation.
Ryan Gavin: ‘Differentiation’ is two things. It’s both different, and it’s valued. And that second one is what gets lost. Yes, we built something different, but how valued is it? If it’s not valued, then you don’t have differentiation.
What’s your advice for marketing leaders navigating this AI transformation?
Ryan Gavin: We cannot let go of the responsibility for the quality of the content and output. As marketers or as business leaders, we can’t let AI allow us to turn our brains off. We have to stay very vigilant and have QA systems that we’re checking on.
Kelly Waldher: Stay curious and connect that to business outcomes. We have this moment happening right now where everything we do as marketers is being transformed, disrupted, and going to change. If you stay curious as marketers and you think about how you can connect that curiosity to driving business outcomes, amazing things will happen for you in your career.
About the Visionaries
Kelly Waldher, CMO, Zendesk
Kelly Waldher is Chief Marketing Officer for Zendesk and responsible for leading the company’s global marketing, communications and social impact team, building the Zendesk brand, and delivering world-class demand.
Ryan Gavin CMO, Slack
Ryan Gavin is the Chief Marketing Officer (CMO) of Slack at Salesforce, where he leads global marketing efforts for one of the most innovative and beloved work platforms, reshaping team productivity in the age of AI and agents.
Interview by Kathy Hollenhorst, Marketers That Matter® Advisor & Chief Community Officer
Visionaries airs live on Zoom every month and is brought to you in partnership with The Wall Street Journal. In each episode, two new Visionaries share their game plan and how that impacts today’s teams, talent, and you.
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