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. About UsJennifer MarloHead of Content, CommerceNextJennifer Marlo drives industry-leading programming at CommerceNext, drawing on experience from Ascendant Network and iMedia Connection, where she spearheaded content strategies to inspire retail, brand and agency marketing leaders. Guided by the belief that “a rising tide lifts all boats,” Jennifer uses in-person and digital platforms to educate and foster industry collaboration. Steve Dennis is a strategic advisor and keynote speaker focused on growth and innovation, who has also been named one of the world's top retail influencers. He is the bestselling authro of two books: Leaders Leap: Transforming Your Company at the Speed of Disruption and Remarkable Retail: How To Win & Keep Customers in the Age of Disruption. Steve regularly shares his insights in his role as a Forbes senior retail contributor and on social media.Michael LeBlanc is the president and founder of M.E. LeBlanc & Company Inc, a senior retail advisor, keynote speaker and now, media entrepreneur. He has been on the front lines of retail industry change for his entire career. Michael has delivered keynotes, hosted fire-side discussions and participated worldwide in thought leadership panels, most recently on the main stage in Toronto at Retail Council of Canada’s Retail Marketing conference with leaders from Walmart & Google. He brings 25+ years of brand/retail/marketing & eCommerce leadership experience with Levi's, Black & Decker, Hudson's Bay, CanWest Media, Pandora Jewellery, The Shopping Channel and Retail Council of Canada to his advisory, speaking and media practice. Michael produces and hosts a network of leading retail trade podcasts, including the award-winning No.1 independent retail industry podcast in America, Remarkable Retail with his partner, Dallas-based best-selling author Steve Dennis; Canada's top retail industry podcast The Voice of Retail and Canada's top food industry and one of the top Canadian-produced management independent podcasts in the country, The Food Professor with Dr. Sylvain Charlebois from Dalhousie University in Halifax. Rethink Retail has recognized Michael as one of the top global retail experts for the fourth year in a row, Thinkers 360 has named him on of the Top 50 global thought leaders in retail, RTIH has named him a top 100 global though leader in retail technology and Coresight Research has named Michael a Retail AI Influencer. If you are a BBQ fan, you can tune into Michael’s cooking show, Last Request BBQ, on YouTube, Instagram, X and yes, TikTok. Michael is available for keynote ...
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