AI in eCommerce marketing isn’t about “better prompts” anymore, it’s about better systems. Brett sits down with returning guest Russ Henneberry (TheClick.ai, co-author of Digital Marketing for Dummies) to unpack what’s new and what’s next: Claude Cowork, agentic workflows, skills that “self-improve,” and what happens when your AI can actually use your files, tools, and data — not just chat about it.

If you’re a DTC founder, CMO, or operator trying to scale performance without scaling headcount, this episode is a blueprint for how modern teams are building repeatable AI routines for content, reporting, and decision-making.

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Sponsored by OMG Commerce - go to (https://www.omgcommerce.com/contact) and request your FREE strategy session today!

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Chapters:

(00:00) Intro

(02:05) What Cowork is: agentic plans, local files, and “skills”

(05:20) Skills that self-improve, plus persona + offer as core context

(08:10) Cowork as a “brain” with version control, shared across workflows

(10:10) Connected sources: Notion transcripts, Zoom notes, and MCP-style integrations

(15:10) Parallel agents and context windows: why this runs faster than chatbots

(18:05) Skill marketplaces, sharing zips, and the security caution

(23:10) OpenClaw/Open-source talk: the 4 “levels” (chatbot → cowork → code → open source)

(28:05) Hardware reality: Mac Minis, Apple silicon, and “processing power” as leverage

(31:05) Content system: Source → Structure → Format → Polish (newsletter example)

(38:30) Click.ai membership, team training, and closing thoughts on revenue/employee

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Connect With Brett:

LinkedIn: https://www.linkedin.com/in/thebrettcurry/
YouTube: https://www.youtube.com/@omgcommerce
Website: https://www.omgcommerce.com/
Request a Free Strategy Session: https://www.omgcommerce.com/contact

Relevant Links:

Russ’s LinkedIn: https://www.linkedin.com/in/russhenneberry
theCLICK: https://theclick.ai/
Digital Marketing for Dummies: https://www.amazon.com/Digital-Marketing-Dummies-Business-Personal/dp/1119235596

Past guests on eCommerce Evolution include Ezra Firestone, Steve Chou, Drew Sanocki, Jacques Spitzer, Jeremy Horowitz, Ryan Moran, Sean Frank, Andrew Youderian, Ryan McKenzie, Joseph Wilkins, Cody Wittick, Miki Agrawal, Justin Brooke, Nish Samantray, Kurt Elster, John Parkes, Chris Mercer, Rabah Rahil, Bear Handlon, JC Hite, Frederick Vallaeys, Preston Rutherford, Anthony Mink, Bill D’Allessandro, Stephane Colleu, Jeff Oxford, Bryan Porter and more