The GTMnow Newsletter (by GTMfund)

The GTMnow Newsletter (by GTMfund)

The GTMnow Newsletter (by GTMfund)
The GTMnow Podcast
Why Old Playbooks Are Breaking and How AI Assisted GTM Actually Works | Dave Boyce
0:00
-35:49

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

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Sophie Buonassisi's avatar
GTMnow and Sophie Buonassisi
Dec 10, 2025

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Brought to you by: 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.

Who we sat down with

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

View the Full Transcript

Key takeaways

1. GTM is finally being treated like an engineered system.
Most GTM teams still run on analogies, habits, and heroic reps instead of explicit design. The companies pulling away are treating revenue like manufacturing or aviation—instrumented, monitored, and continuously improved, with AI as “robots on the line” rather than random tools.

2. Your buyer already did the discovery.
Old rules like “never demo without discovery” and “never give price until you reach the budget owner” assume information scarcity on the buyer side. Today’s millennial and Gen Z buyers know the options, the pricing, and the reviews before they ever talk to sales, which means GTM has to meet them where they are, not force them into dated motions.

3. Assistive AI sets the floor, not the ceiling.
Email writers, meeting summarizers, and AI coaching are table stakes and will quickly become the new baseline for individual productivity. Durable advantage comes from engineering growth as a system and then assigning “robots” (AI agents) to specific jobs within that system.

4. Robots need onboarding too.
You can’t just buy an “SDR bot” and expect magic the next day. Just like humans, AI agents need a designed system, clear responsibilities, training data, guardrails, and ongoing coaching—once that’s in place, they don’t forget, don’t tire, and can scale in ways humans can’t.

5. PLG is just empathy, generosity, and metrics at scale.
Modern freemium playbooks start with deep empathy for the end user’s job to be done, give away enough value generously to build habit, and then rely on product analytics to observe, learn, and tune. If you’re not instrumented, you’re guessing—and guessing doesn’t scale.

6. Self-service is a one-way trend.
In your own life, you rarely talk to a human to buy gas, groceries, or apps. Your customers feel the same way about software: if your competitor lets them trial and succeed on their own while you gate everything behind a demo, you’re training them to choose the competitor.

7. The right side of the bow tie is where compounding lives.
Most leadership attention, budget, and headcount still cluster around “calling and hitting the bookings number.” The bow tie model makes it painfully obvious that renewals, expansion, and customer-driven growth loops on the right side are where long-term compounding really happens.

8. AI can finally make complex products feel simple enough for self-serve.
AI isn’t just about speeding up existing workflows; it can also de-complexify entire product categories that used to require months of human-led onboarding and configuration. That unlocks PLG-style motions even for heavyweight enterprise tools that were previously “too complex.”

9. Revops has to become the backbone, not the reporting team.
If RevOps’ job is just to make the CRO look good in board meetings, the system will never get truly instrumented. To run AI experiments, bow tie analytics, and continuous GTM tuning, RevOps needs to be the objective owner of the data model and truth, not a political function.

10. Leaders must shift from “I know the playbook” to “we’ll figure it out.”
There is no 15-year-old manual for AI-assisted GTM or PLG + agents; nobody grew up selling this way. The best executives are showing up as “chief figure-it-out officers,” bringing smart people together to run experiments rather than recycling war stories from a different era.

Follow Dave Boyce

Product-led GTM
Content from and related to the book FREEMIUM, published by Stanford University Press.
By Dave Boyce

Recommended books

  • Freemium by Dave Boyce
    A practical playbook for building and transforming into self-service, product-led, and freemium models—especially for companies that weren’t born PLG.

  • Competing Against Luck by Clayton Christensen
    The definitive exploration of Jobs to Be Done and how customers “hire” products to make progress, which heavily informs Dave’s approach to empathy and product design.

  • Playing to Win by Roger Martin
    A concise strategy framework Dave leans on for making clear choices about where and how to compete.

Referenced

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The GTMnow Podcast tells the stories of how the top 1% of operators, founders and investors build, scale and invest.

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