Why Old Playbooks Are Breaking And How AI Assisted GTM Actually Works

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Why Old Playbooks Are Breaking and How AI Assisted GTM Actually Works | Dave Boyce

6d ago 35:49

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Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Design’s Growth Institute, works with leadership teams on Bow Tie–based growth models, and is all-in on how AI will reshape GTM as a true engineered system.

Discussed in this episode

Why classic sales & marketing playbooks haven’t caught up to how modern buyers actually buy.
How the Bowtie model exposes the real levers of growth that funnels hide.
Why PLG-style thinking is now essential even for sales-led and enterprise motions.
The 3 first principles of freemium: empathy, generosity, and metrics.
Where AI can reliably outperform humans across the customer journey, and where it absolutely shouldn’t.
How to design hybrid human + AI workflows using a clear data model, not vibes.
What RevOps should own in a modern revenue architecture (and why it can’t just serve the CRO narrative).
Hard-earned founder lessons from Fundly on reinvention, calling bets early, and letting go of old branches.

Episode highlights

00:00 — GTM is still running 20-year-old playbooks

01:29 — “Sales, marketing, CS… the last unengineered engine”

03:20 — The myth of “just add more heads”

05:50 — The Fundly story: reinvention, too late

08:30 — Why Freemium had to be written

11:01 — Three first principles of freemium

15:25 — Mapping AI across the entire customer journey

19:29 — “Automate the predictable, humanize the exceptional”

25:18 — What the Bowtie exposes that funnels hide

27:25 — Building a “minimum viable Bowtie

This episode is brought to you by our sponsor: ZoomInfo

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Dave Boyce (Guest)

LinkedIn: https://www.linkedin.com/in/boycedave
Substack: https://daveboyce.substack.com

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The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.

Chapters

1. Why Old GTM Models Are Failing (00:00:00)

2. Buyers In Control, Playbooks Outdated (00:02:45)

3. PLG As The Engine Of Modern Growth (00:05:10)

4. Founder Lessons: Reinvention And Timing (00:08:30)

5. The Spark Behind The Freemium Book (00:12:40)

6. Three First Principles: Empathy, Generosity, Metrics (00:15:40)

7. Where AI Outperforms Humans Across The Journey (00:19:10)

8. Automate The Predictable, Humanize The Exceptional (00:23:40)

9. Building A Data Model And Running Experiments (00:27:20)

10. The Bowtie Model And Compounding Growth (00:31:00)

11. Minimum Viable Bowtie And Instrumentation (00:35:00)

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