In this episode of CMOs Anonymous, we sit down with Tony Gruebner, current VP of Brand at UpGuard and previous CMO at Pepperstone, former data and strategy lead at Sportsbet, to unpack what it really takes to be a modern marketer. From his roots in analytics to launching global brand campaigns, Tony shares how a background in data helped shape his approach to creativity, leadership, and cutting through the noise.

Tony opens up about the evolution of the CMO role—from a traditional marketing lane to someone who must now speak the language of finance, tech, and product. He reflects on his early days building player value models at Sportsbet, the challenges of bringing paid media in-house, and how knowing your way around a spreadsheet can set a marketer apart. This is actionable listening for any aspiring marketing leader.

We also dive into the thinking behind Pepperstone’s "Fine With It" campaign, where John McEnroe launched tennis balls (and punchlines) in a bold brand play that stood out in a sea of serious, finance-focused ads. Tony explains why humor was used not just to entertain, but to signal confidence, break through sameness, and connect emotionally with an audience that doesn’t always take themselves as seriously as the category suggests.

We discuss the realities of AI in marketing—where it’s helping, where it’s overhyped, and why the real value lies in reimagining how we work, not just speeding up what we already do. Tony shares how AI might reshape customer experience through natural language interfaces and ponders the idea that the best CMOs of the future will be those who can translate—between data, creativity, and business impact.

Finally, for up-and-coming marketers, Tony offers simple but powerful career advice: look beyond your job description. Don’t wait for permission. Learn the business. Talk to finance. Sit with data teams. Ask better questions. His biggest learning? Success often comes from doing the job above the one you’re in—and being the person who connects dots that others can’t see.

Packed with smart takes, sharp humour, and generous insights, this episode is a must-listen for marketers navigating the balance between art, science, and leadership in an AI-powered world.