In this episode of 909 Exec, host Den Jones sits down with longtime friend and mentor Toni Vanwinkle, Adobe’s leader for Digital Employee Experience and co-chair of AI, to explore how technology, disruption, and human-centered leadership are reshaping the future of work. Toni shares her nonlinear “career lattice” journey from aspiring artist to finance professional, then into consulting and large-scale enterprise transformations at Cisco, before spending 16 years at Adobe in multiple roles. Along the way she discovered a passion for technology as a powerful way to solve business problems, implementing early automations and ERP systems, and learning how organizational change management is essential to bringing people along in any transformation. She opens up about pivotal personal decisions—like leaving a high-stress role to pursue consulting so she could prioritize starting a family—and how she and her husband redesigned their careers to create a sustainable “container” for work and parenting. Toni explains why you can have it all, just not all at the same time, and how aligning career moves with life needs and values has guided her path. Den and Toni dive into the trap of “work, work, work” in your 20s, and why so many professionals are blind to the need to prioritize their physical, financial, and spiritual health, as well as their broader sense of purpose. Toni encourages people to see themselves as multidimensional, drawing on her own artistic background to show how creativity can fuel even highly technical roles. The conversation then turns to the future of work and the transformative impact of AI. Toni outlines three key questions she uses to reimagine work: Do we still need to do this work? How can technology augment us as a thought partner? And what can we safely automate and delegate to machines? She envisions a future where humans provide context, creativity, and critical thinking, while AI accelerates consistency, reasoning, and problem-solving. As co-chair of AI at Adobe, Toni discusses how the company is embedding AI into products while maintaining a foundation of trust—focusing on security, ethics, and bias in models—and why educating employees on both AI proficiency and “human in the loop” responsibility is critical. She emphasizes that humans remain accountable for outcomes, even when AI is involved, and notes that bad actors are also using AI, which raises the stakes for security. Den and Toni compare the AI boom to the early web era, agreeing that AI will dwarf previous technology shifts in impact. They explore how AI is already accelerating work—from building internal tools and quizzes in minutes instead of weeks, to rethinking build-vs-buy decisions for enterprise software—while acknowledging that large-scale enterprises still need robust data, governance, and security layers. Throughout, they return to themes of wellbeing and sustainability in high-intensity operational roles, likening security and operations leaders to first responders. Toni argues that leaders must actively “bench” exhausted team members and continually reassess what they value—impact, relationships, spiritual and physical health, or time outdoors—so they can make conscious tradeoffs instead of unconsciously sacrificing their lives to work. To close, Toni shares what recharges her outside of work: time at the beach in any weather, the sense of wonder she finds in her garden, and the visceral energy she gets from live music. Den adds his own love of gardening, wine, and concerts, underscoring their shared belief that a rich life outside the office fuels better leadership inside it.
