Ep 5: Reimagining Marketing and Team Structure in the Age of AI: What's Working and What's Not with Jon Miller

In this episode of GTM by the Numbers, Brandon Redlinger chats with Jon Miller to rethink how marketing and revenue teams should operate when AI is at the core—not bolted on. Jon breaks down where AI is already working (inbound agents, agentic workflows that compress prep/follow-up) and where it isn’t (spray-and-pray outbound “personalization” without human oversight). He explains why to avoid multi-year vendor lock-in during this transition, how “AI-curated playlists” will replace rigid nurture streams, the emerging shape of GTM orgs (fewer SDR bodies, rise of GTM engineers), and how to measure AI’s impact through efficiency and effectiveness with pipeline and revenue still as the gate.

In this episode, we break down:

• Why bolting AI onto 15–25-year-old, rules-based systems is “lipstick on a pig”, and what it looks like when reasoning replaces rules.
• The “AI DJ” model: 1:1 orchestration that curates a personalized playlist of actions for every contact (goodbye, one-size-fits-all nurtures).
• Agentic AE workflows that auto-build account plans, research, and follow-ups so reps spend less time prepping and more time selling.
• AI SDRs: why inbound agents shine (speed + always-up-to-date) and why outbound still needs real human oversight.
• Measuring AI with hard ROI on efficiency (time saved) vs. harder-to-measure effectiveness (synthetic panels, engagement lift, pipeline).
• How AI will disintermediate your marketing (search today, inbox tomorrow) and what survives (experiences, relationships and craftsmanship)

Resources mentioned in this episode:

Claude (Anthropic): Jon and Brandon reference using Claude for building and experimenting with AI workflows and prototypes.

https://www.anthropic.com/claude

Lovable: “Vibe-coding” tool Jon and Brandon discuss for quickly prototyping apps/sites to convey product vision.

https://lovable.dev/

Clay + HubSpot integration: Used by Brandon to automate research, notes, and follow-ups in GTM workflows.

https://www.clay.com/university/guide/hubspot-integration-overview

All-In Podcast: One of Jon’s go-to listens to understand diverse viewpoints.

https://allin.com/

Christopher S. Penn / Trust Insights: Jon’s recommended source for staying current on marketing AI.

https://www.trustinsights.ai/blog/

From Impossible to Inevitable (Aaron Ross & Jason Lemkin): Quoted during the selling-time discussion.

https://fromimpossible.com/

Connect with Jon at LinkedIn: https://www.linkedin.com/in/jonmiller2

Connect with Brandon at linkedin.com/in/brandonredlinger

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