Anne Bologna doesn’t just do strategy, she lives it. As the Chief Strategy Officer at Crossmedia USA, Anne brings decades of experience across creative, media, and client-side roles to the table. In this episode, she joins us to talk about how strategy really works in today’s media chaos, from aligning KPIs to the art of the single, powerful brief.

Matthew Mottola, CEO of Human Cloud and longtime evangelist of the freelance economy, joins us to unpack the open-talent model. From starting as a college freelancer to building tech that powers the flexible workforce, Matthew’s journey is all about helping enterprises rethink how work gets done. We cover what “flexible talent” really means and what it takes to build the future of work—from the inside out.

Kay Bradley⁠, CMO of Chicago Stars FC, joins us to unpack the evolving landscape of sports marketing. From breaking down barriers in women’s sports to building a brand fans can rally around, she brings a marketer’s eye and an athlete’s heart to one of the fastest-growing movements in sports.

Brilliant strategist and amazing human Rich Santiago shares insights on his amazing career working on some of the world’s most interesting brands. Hear how he got started, what he does to stay in tune with the latest, and where you can check out what he’s up to next.

Topics

• Where he started – How Rich found his way to becoming a planner
• Precious, not precious – Being very precious about the human experience and truth, but not the small stuff.
• Going back to the Beans – Reimagining the Starbucks brand
• Bigger than just commercial impact - Hear how the work Rich most admires and is proud of hits big, both commercially and culturally
• Learning & Sharing - Being mentored by some of the best and paying it forward

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