A major leader in advertising and business: Jill Smith, the Americas CEO of Iris Worldwide, an integrated creative agency. With over 15 years of experience across startups, agencies, and global brands in North America, Europe, and China, her journey is nothing short of inspiring.

She’s also a faculty member at The New School, teaching entrepreneurship and social innovation, and an early-stage startup investor and advisor. Alongside leading an advertising company, she’s a boy mom and passionate about extreme endurance sports.

In this episode, we sit down with Shiri — aka the Sephora girl — a freelance copywriter and creative strategist behind some of the biggest beauty brands. Shiri shares what it’s really like behind the scenes of beauty marketing. She talks building a long-term career, mastering your niche, and why showing up online (even if you don’t want to) can open unexpected doors. If you’re dreaming of working with major brands, this episode is your roadmap.

Chelsea Jane Sillars Sailing is an accomplished Creative Producer and Art Director with over 15 years of experience in the fashion industry. She has served as Senior Producer for Annie Leibovitz and held standout roles at iconic brands such as Rag & Bone and Faherty. Chelsea began her career producing large-scale fashion shoots—including numerous Vogue covers—and a performance at The Louvre. Since then, she has evolved into a creative force behind some of the industry’s most celebrated brands and professionals.

From long nights on set to carving out her own path, Chelsea has truly done it all. In this episode, we dive into the realities of working in-house for a brand versus the freedom and hustle of freelancing. We also explore what it takes to stay grounded and prioritize wellness while navigating fast-paced creative environments.