Future of Retail Speaker, Former Walmart Executive & Startup CMO

Toronto, Canada
Live Event: $10,000 - $20,000 Virtual Event: $5,000 - $10,000 More Fee Info

Drew Cashmore Biography

Drew Cashmore was the original architect of and former executive at Walmart Connect, Walmart's retail media business in U.S. and Canada. Over his 13 years at Walmart, Drew helped develop the concept and manage the internal and market change required to establish Walmart as a $2BN+ Retail Media powerhouse. This included insourcing the business, establishing the brand and sales enablement practices, leading internal change management, and developing the in-store advertising strategy. During this time at Walmart, Drew was also a founding member of Walmart eCommerce in Canada and the leader of Walmart's first in-house digital B2C marketing team.

As the former CMO of Firework, a Softbank-backed B2B video commerce SaaS platform, Drew shaped a new cottage industry for retail in the West, acting as a thought leader across North America, Europe and Asia Pacific regions.

Drew is the founder of Adaptive Retail Group including Adaptive Retail Collective and Adaptive Retail Technologies, a new series of startups establishing a resilient model for change in retail.

Outside of his day-to-day, Drew is startup advisor, investor in scalable tech and education platforms and father of two amazing kids. He received awards for both Top 30 Under 30 in Marketing and Top 40 Under 40 in Retail Innovation. Drew is a public speaker, thought leader, writer, aspiring actor (one can still dream), and shared keynote addresses at events including Shoptalk, GroceryShop, The Lead Innovation Summit, Smart Retail Tech and more.

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Speaker profile last updated by AAE Talent Team on 09/16/2025.

Drew Cashmore Speaking Topics

  • The Second Order Effects of AI In Commerce: What Happens When...

    The pace of change in retail is accelerating

    • especially with AI. New business models, new customer behaviors, new ways of working. Our businesses are about to go through the most fundamental transformation in shopping ever, and we need to establish a new approach to creating focus and keeping up with this change.

    At Adaptive Retail Group, we spend a lot of time with industry experts scenario planning for the future and determining likely outcomes of a rapidly evolving retail landscape. Our efforts serve to identify the right areas of focus for commerce businesses today to prepare us for tomorrow. We care less about the technology itself, and more about what likely happens to our customer experiences, our team's ways-of-working, and our business models as a result.

    The Second Order Effects talk looks at five specialized use cases for AI in retail, and provides a multidimensional view into what we need to prepare for two to five years out.

    • Generative AI in Search
    • Customer Adaptive Retail
    • Dynamic Store Operations
    • Supply Chain Optimization
    • AI as a new Profit Center

    Essentially, if this use case takes off, what will be the result, and how will we need to transform our businesses or experiences today to be ready for tomorrow.

  • The Leapfrog Moment in Retail Media: Applying Lessons from the Past to Leapfrog Competitors

    Retail Media has become fraught with fragmentation and conflicting narratives. The rapidly growing space risks further consolidation into Amazon, Alibaba and Walmart if something isn't done to change the trajectory.

    With all of the new and emerging retail media businesses, brands, agencies and vendors looking to dive into the space, one thing remains true

    • we keep repeating the same mistakes. Luckily, we're at a moment in time whereby new or growth entrance can leapfrog the incumbents by learning from the people who have lived it before.

    Having spent over a decade building and scaling Walmart Connect to a $2BN+ retail media powerhouse

    • focused on everything from general management to business model transformation, merchant change management, commercialization and in-store strategy

    • Drew knows how it works, how it really works.

    The Leapfrog Moment in Retail Media session is designed for retailers, brands, agencies and vendors who are looking to build from today, for tomorrow, and sidestep many of the mistakes we made in the very early days of this thing.

    We touch on topics including:

    • The truth about trade, shopper and brand dollars
    • How much is possible and at what stage
    • Architecting teams, finding the right people
    • Establishing a customer-centric approach vs. a pure profit centre
    • Managing change across merchandising and marketing
    • The biggest mistakes made

    This talk is about establishing the right foundation for today from someone who lived and scaled a customer-centric retail media model within the world's largest retailer.

Read More +

Drew Cashmore Videos

Commerce in Motion | Drew Cashmore of Firework

Commerce in Motion | Drew Cashmore of Firework

Drew Cashmore, Global Head of Marketing for Firework joined our recent TechTO: Retail to share how commerce is evolving from his perspective To...

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  • What are the speaker fees for Drew Cashmore

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  • What topics does Drew Cashmore speak about?

    Drew Cashmore is a keynote speaker and industry expert whose speaking topics include Business, Corporate Strategy, E-Commerce, Entrepreneurship, Finance, Innovation, Marketing, Retail, Sales, Strategic Leadership
  • Where does Drew Cashmore travel from?

    Drew Cashmore generally travels from Toronto, Canada, but can be booked for private corporate events, personal appearances, keynote speeches, or other performances. For more details, please contact an AAE Booking agent.
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Drew Cashmore is a keynote speaker and industry expert who speaks on a wide range of topics such as The Second Order Effects of AI In Commerce: What Happens When..., The Leapfrog Moment in Retail Media: Applying Lessons from the Past to Leapfrog Competitors, If Everybody was a Merchant: How Video is Changing the Dynamic of Shopping and Customer Adaptive Retail: Architecting our Businesses to Rapidly Adopt the 'New'. The estimated speaking fee range to book Drew Cashmore for your event is $10,000 - $20,000. Drew Cashmore generally travels from Toronto, Canada and can be booked for (private) corporate events, personal appearances, keynote speeches, or other performances. Similar motivational celebrity speakers are Gisel Ruiz, Alexandra Wilkis Wilson, Michael Bergdahl, Terence Reilly and David Kahan. Contact All American Speakers for ratings, reviews, videos and information on scheduling Drew Cashmore for an upcoming live or virtual event.

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