On this episode of Conversations with CommerceNext, host Michael LeBlanc welcomes Jenna Flateman Posner, Founder & CEO of Chief Digital Agency. Jenna reflects on her transition from tech partnerships to retail leadership at Snipes and Solo Brands, and why she launched her own agency to bridge the gap between vendors and retailers. She shares candid advice on vendor-retailer relationships, the future role of AI, and why data pipelines—not websites—are today’s critical digital priority.
In this episode of Conversations with CommerceNext, host Michael LeBlanc sits down with Jenna Flateman Posner, Founder & CEO of Chief Digital Agency, for a candid and insightful conversation on the changing dynamics of retail technology and digital transformation.
Jenna shares her remarkable career journey, starting on the technology side, building go-to-market partnerships in loyalty, payments, and localization before making the leap into retail operations as VP of Digital and then Chief Digital Officer at Snipes. She reflects on scaling Snipes’ digital business from $7 million to $100 million, navigating the pandemic, civil unrest, and the accelerated shift to digital commerce.
From there, Jenna moved to Solo Brands, where she drove digital strategy across a portfolio of outdoor lifestyle companies and activated memorable campaigns, including the award-winning “smokeless” collaboration with Snoop Dogg. These experiences ultimately inspired her to found Chief Digital Agency, a consultancy designed to bridge the persistent gap between technology vendors and retail operators.
Jenna describes her role as a translator and conduit between retailers and technology providers—helping vendors refine products, craft go-to-market strategies, and close deals, while assisting retailers with tech selection, vendor management, and implementation oversight. By bringing transparency and empathy to both sides, she helps organizations avoid costly missteps and unlock true partnership value.
The conversation dives deep into some of retail’s most pressing challenges: why cultural and organizational silos slow down tech adoption, the need for retailers to embrace faster decision-making, and the importance of vendors building trust instead of chasing cold-call volume. Jenna also shares her vision for the future of digital commerce, where AI acts as a unifying operating system and data pipelines—not websites—become the core infrastructure for brand success.
With practical advice for vendors, retailers, and technologists alike, this episode offers a roadmap for building stronger relationships, embracing risk, and preparing for a future shaped by AI-driven agents and new consumer expectations.
Tune in to hear why Jenna believes digital leaders must become “data people” first—and how Chief Digital Agency is shaping the future of retail partnerships.