In this episode, we sit down with Zain Lakhani, Chief AI Officer at Pendo, to explore what it actually means to own AI strategy inside a mature SaaS company. At just 23, Zane leads an org that is figuring out where AI belongs in the product, the engineering workflow, and the business as a whole.
Zain shares how his consulting background gave him a sharp instinct for telling real AI use cases from AI for AI’s sake, and how that led him to see a bigger opportunity at Pendo: reframing what the company has sold for years to a new, AI-native audience. He opens up about the early temptation to chase every shiny new model, why most of that work was throwaway, and how it still built a culture of fast experimentation.
He also digs into leading teams through adoption. You’ll hear how his team grew daily Claude usage from 15% to 45% of the company, why resistance usually comes from a lack of proof rather than a fear of AI, and how to channel power users so they set an example of what good looks like rather than what reckless looks like. Along the way, he explains why prototyping has become one of the most undervalued skills on any team, and how Pendo’s once non-technical CEO became one of its biggest product contributors. He closes with the topic he thinks is being overlooked: governance and access permissions for AI agents.
Whether you’re an executive without a technical background, a leader trying to move your team past the hype, or a professional wondering how to position yourself in an AI-driven market, this episode offers candid, practical perspective from someone building in the thick of it.
Want more marketing resources? Check out nativedigital.com/resources for our free PDF frameworks on messaging, channel strategy, and market fit.
11 Nov 2025
David Lee - Chief Brand & Creative Officer at Squarespace
In this episode, we sit down with David Lee, Chief Creative Officer at Squarespace, to trace his journey from a restless teenager in suburban Montreal to leading one of the most design-forward companies in the world.
David shares how skate culture and DIY design first opened his eyes to creativity, what he learned at the Rhode Island School of Design (including the life-changing lesson of drawing with his left hand), and how he carved his path through some of the world’s top creative agencies like Sid Lee, AKQA, and Wieden+Kennedy, before making the bold leap into tech.
He also reflects on building Squarespace’s in-house creative team, embracing risk, and the role of self-awareness as the most valuable career investment. From navigating imposter syndrome to leading creative teams through technological disruption, David’s story is a masterclass in staying curious, adaptive, and human in a rapidly changing world.
30 Oct 2025
Jeremy Jones - Global Head of Creative at Mailchimp
In this episode, we explore the unconventional path of Jeremy Jones, who transformed his passion for punk rock, skateboarding, and counter-culture creativity into a thriving advertising and marketing career. Jeremy shares how making band flyers and touring with musicians became his informal MBA in marketing, teaching him branding, promotion, and creative problem-solving long before he understood what advertising actually was.
Discover how Jeremy's creative partnership—formed through both bandmate chemistry and advertising collaboration—propelled him through agency ranks, culminating in representing Team USA at Cannes Young Lions. His journey spans radio promotion, boutique agencies, and eventually a global role at J. Walter Thompson before making the pivotal leap to building MailChimp's acclaimed in-house creative team, Wink.
Jeremy reveals the philosophy behind MailChimp's distinctive "expert absurdist" brand voice and shares insights from memorable campaigns like "Email Is Dead" and "The Customer." He emphasizes the importance of bringing organization and belief to creative teams, understanding client businesses deeply, and marketing to marketers in ways that inspire rather than bore.
The conversation offers invaluable guidance for creatives at every stage: students should lead with passion over perfection, early-career professionals must raise their hands for opportunities, and new leaders need to stay connected to the work while investing in relationships outside their industry. Jeremy's advice on "fishing in other rivers" and maintaining hobbies for creative rejuvenation provides a refreshing perspective on sustainable creative leadership.
Whether you're an aspiring creative, agency professional, or in-house marketing leader, this episode delivers authentic wisdom from someone who built his career on curiosity, relentless work ethic, and never forgetting the scrappy, DIY spirit that started it all.
Who has been a guest on From Here To There
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John Lewis Gaddis
Joel Grabenstein
Alistair Croll
Amber Armstrong
Cole Nussbaumer Knaflic
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