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The Watson Weekend

The Watson Weekend

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Welcome to The Watson Weekend – a rollicking weekly live conversation (and dance party) about all things retail, tech, and ecommerce! Hosts Rick Watson and Jess Lesesky and guests from all around the ecommerce world cut through the BS and bring you no-nonsense conversation, deep insights, and opinions that aren’t afraid to be contrarian. Join us for the livestream every Friday at noon on LinkedIn at https://www.linkedin.com/in/ecommercestrategyconsulting/ and YouTube at https://www.youtube.com/playlist?list=PLMXgOk2gTui7w3ZAZxs95Qz_pcDX17K_cand then listen to the podcast and series a week later – your water-cooler game will always be on point! For media and sponsorship inquiries, please contact mediasales@rmwcommerce.com This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpCopyright 2025 RMW Commerce Persönliche Finanzen Politik & Regierungen Ökonomie
  • Search Is In An Advantageous Position For AI-based Commerce with John Andrews
    Oct 12 2025

    The latest Watson Weekend podcast episode, hosted by Rick Watson and Jessica Lesesky, discusses recent retail developments, including the elimination of the de minimis rule impacting U.S. imports, Starbucks' Taylor Swift-themed in-store experience to regain customers, Instacart 's integration with Tiktok for retail media targeting, and Paypal 's 5% cash back offer on BNPL purchases to boost holiday sales.

    The Watson Weekend is sponsored by Mirakl because growth isn't about just speed. It's about direction. Miracle gives you the infrastructure to scale smarter, not just faster, with marketplace, dropship, retail media, and a seller platform built for what's next and powered by AI.

    The episode features an interview with John Andrews, CEO and Co-founder of Cimulate, who shares his extensive e-commerce background from Endeca to Nike and now AI-driven commerce. John explains how Cimulate uses large language models and synthetic personas to enhance search and merchandising by understanding customer intent and context, enabling more personalized and conversational shopping experiences. He stresses that while AI advances are transformative, human merchants remain vital, and retailers must prepare for rapid shifts in commerce technology..

    Welcome to The Watson Weekend - 00:00:00

    Headline Hangover - 00:03:15

    Introducing John Andrews - 00:19:00

    Shopping in 2028 - 00:25:02

    What's different - 00:36:05

    Search is not solved 00:40:22

    Are retailers ready for an agentic world? - 00:53:41

    End of the show 1:02:56


    #watsonweekend #ai #artificialintelligence #agenticcommerce #search



    This podcast uses the following third-party services for analysis:

    Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
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    1 Std. und 5 Min.
  • The Internal Conflicts Retail Media Networks Create Inside Retailers and Brands with Kiri Masters
    Oct 5 2025

    Watson Weekend hosts Rick Watson and Jessica Lesesky cover the latest retail industry news and trends this week. The headline hangover includes Gen Z's influencer-driven purchases, Mastercard's entry into retail media advertising, potential U.S. government influence over TikTok's algorithm, and Stripe's AI-powered commerce platform.

    Guest Kiri Masters, a retail media analyst, discusses the complexities of retail media networks, internal conflicts within retailers and brands, and the evolving role of AI and large language models in retail advertising and shopping.

    They explore challenges in aligning retailer and brand goals, the impact of agentic commerce on retail media, and the importance of customer loyalty and differentiation beyond price competition.

    The conversation highlights the potential for AI to transform retail media, creative, and customer experiences, while acknowledging current limitations and organizational hurdles.

    The Watson Weekend is sponsored by Mirakl — Because “Traditional eCommerce” Is Just Code for “Not Growing.” Join 450+ retailers scaling 6X faster with AI, automation, and enterprise-grade marketplaces, dropship, and retail media. It’s time to accelerate with Mirakl.

    Chapters:

    Welcome to The Watson Weekend - 0:00

    Headline Hangover 03:08

    Introducing Kiri Masters 18:07

    Internal conflicts within retailers and brands

    The evolving role of AI and large language models

    The challenges of alignment between retailer and brand goals


    #watsonweekend #retailmedia #retailer #brand #widget #perfectcompetition



    This podcast uses the following third-party services for analysis:

    Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
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    1 Std. und 15 Min.
  • Influencer Marketing Should Be A Car That Can Be Driven Anywhere with Kristen Wiley
    Sep 28 2025

    The Watson Weekend hosts Rick Watson and Jessica Lesesky discuss recent retail headlines, including Amazon's $2.5 billion lawsuit over alleged Prime subscription deception, Walmart's significant referral traffic from ChatGPT, Sephora's new affiliate program aimed at beauty creators, and Meta's talks with Google to enhance ad targeting using AI.

    They then interview Kristen Wiley, founder and CEO of Statusphere, a platform that enables brands to generate thousands of influencer posts efficiently by focusing on micro-influencers. Kristen shares her background as a creator and marketer, the slow and strategic growth of Statusphere, and the importance of providing a strong creator experience with human support alongside AI tools.

    She highlights how Statusphere helps brands achieve brand-safe content at scale, integrates influencer marketing across various campaign types, and addresses challenges like attribution and product-market fit.

    Kristen also discusses the evolving role of AI in marketing, the value of authentic human-generated content, and the potential for influencer data to influence AI models. The episode highlights the increasing importance of creator-driven marketing and the necessity for brands to cultivate communities and employ multi-channel strategies.

    Welcome to The Watson Weekend - 00:00

    Headline Hangover 02:56

    Introducing Kristen Wiley 15:47

    The importance of solving the creator experience 23:40

    Human touch in a post-AI world 25:33

    Using micro-influencers vs celebrities 28:25

    Generating ROI 30:52

    Attribution and its influencer challenge 35:00

    Nightmare situations 38:15

    Product Market fit to validate the need for 42:20

    Statusphere community and content 43:40

    #watsonweekend #creators #microinfluencer #community



    This podcast uses the following third-party services for analysis:

    Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
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    51 Min.
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