Heading to Vegas this May? Join Josh at Pulse 2026 and come say hi—your oversized fluorescent daiquiri is on him. No catch.

Grab your ticket at gainsightpulse.com and use code UNCHURNED for a special rate.

Knowledge used to be the CSM's edge. Not anymore.

Diane Wu, Global Head of Customer Success & Experience at Google Cloud Security, operates where every touchpoint is mission-critical — and standing still is falling behind. In this episode, she sits down with Brady Bluhm & Josh Schachter of Gainsight to unpack what the CSM role actually becomes when AI handles the knowledge layer. The answer: context, curation, and hyper-personalization at scale.

Diane shares how her team is using NotebookLM and Gemini to compress hours of customer research into minutes, why her best CSMs were the hardest to get onto new AI tools (and why that makes complete sense), and what two-phase AI adoption really looks like on the ground. Brady brings a builder's lens — talking about juggling AI agents, closing 2-year-old CTAs with one prompt, and why the traditional product UI might not survive the next two years.

If you lead a post-sales team or work in customer success, this conversation will reframe how you think about productivity, coverage models, and the human role in an AI-first world.

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Timestamps

0:00 - Preview & introduction

1:40 - Meet Brady Bluhm (Gainsight) & Diane Wu (Google)

3:00 - Diane's role: Google Cloud Security & the post-sales mission

5:25 - The shift from access to curation

8:28 - Brady: how AI is changing CSM onboarding and memory

10:55 - Are you saving time or just doing more?

12:34 - How AI changes coverage models and the 1:many CSM ratio

18:00 - Diane's tactical playbook for running parallel customer analyses

22:05 - Brady's "can I do this with AI?" framework and skill-building loop

24:00 - How much time should you spend tuning your AI setup?

26:31 - Why your top CSMs are the hardest to get on new AI tools

31:21 - LLMs will become the new workspace

32:59 - Two-phase LLM adoption and why the UI is going away

34:15 - Closing 2-year-old CTAs with one prompt

37:47 - Hyper-personalization at scale for Google Cloud

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What You’ll Learn

- Why knowledge is no longer the CSM's differentiator — and what replaces it

- How Diane's team at Google Cloud Security uses NotebookLM as a living customer notebook

- Why your best CSMs resist AI adoption the most

- How AI is reshaping CSM coverage models and the 1:many ratio

- Brady's two-question AI habit that keeps him ahead every week

- What the Gainsight MCP unlocked — and what it means for the future of CS tooling

- Why the traditional application UI may disappear — and what replaces it

- How to create "wow moments" that actually drive AI adoption across your team

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Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

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Where to Find the Guests

Diane Wu's LinkedIn: https://www.linkedin.com/in/diane-wu/

Brady Bluhm's LinkedIn: https://www.linkedin.com/in/bradybluhm/

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Where to Find Josh:

LinkedIn: https://www.linkedin.com/in/jschachter/

Unchurned Substack: https://unchurned.substack.com/

Heading to Vegas this May? Join Josh at Pulse 2026 and come say hi—your oversized fluorescent daiquiri is on him. No catch.

Grab your ticket at gainsightpulse.com and use code UNCHURNED for a special rate.

Watch Eric Gilpin, President of Go-To-Market at G2, reveal how he’s building the first-ever unified revenue org in a 210,000-product marketplace. In this episode, he takes us behind the scenes of G2’s “zero daylight” alignment strategy and how it led to a game-changing 31% YoY traffic spike. Discover why G2 made the controversial bet to let LLMs scrape their data (and why competitors are now paying the price), how to flip buyer intent into “churn intent” to catch customers before they leave, and how the difference between “freelancers” and “contractors” became worth $600M+ in revenue. This is marketplace strategy 101, told by someone who’s spent 25+ years perfecting it. Essential listening for GTM leaders, CS teams, and anyone building in B2B SaaS.

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Timestamps

0:00 - Preview & introduction

1:28 - Meet Eric Gilpin & overview of G2

6:50 - How Upwork scaled from $30M to $650M in gross sales volume

10:00 - Building G2’s first President of Go-To-Market role

11:13 - Zero daylight: Aligning marketing, BDRs, and all revenue teams

16:42 - Pivoting narrative from “SEO review site” to AEO visibility engine

18:15 - G2’s “Hunter Hunter” post-sales org (60% growth from expansion)

21:00 - The highest-value CS activities (hint: it’s not quarterly review sends)

23:23 - Self-serve + AI automation for the 150,000 SMB products

25:23 - The churn intent

27:28 - Why G2 allowed LLMs to train on their data

31:55 - Nostalgia and denial kill businesses

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What You’ll Learn

- How to eliminate silos by achieving “zero daylight” between marketing, sales, and revenue teams

- The whitespace model G2 uses to find expansion revenue

- How to build a “churn intent” system using buyer signals to catch churn before it happens

- Why allowing LLMs to scrape your data early creates a competitive moat

- The subtle power of reframing to unlock enterprise adoption and market perception

- Why is constantly challenging your own status quo the only defense against disruption

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Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

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Where to Find Eric Gilpin

LinkedIn: https://www.linkedin.com/in/ericgilpin/

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Where to Find Josh:

LinkedIn: https://www.linkedin.com/in/jschachter/

Unchurned Substack: https://unchurned.substack.com/

Heading to Vegas this May? Join Josh at Pulse 2026 and come say hi—your oversized fluorescent daiquiri is on him. No catch.

Grab your ticket at gainsightpulse.com and use code UNCHURNED for a special rate.

What does the future of CS actually look like? Ghazi Masood, CRO of Replit, has some strong opinions and the growth numbers to back them up.

In one year, Replit went from $2M to $150M in revenue. Now they're targeting $1B. And while most companies are still debating AI strategy, Ghazi is already rebuilding his entire GTM org around it — scaling from 40 to 230 people, scrapping the traditional CSM model, and betting that the next billion software creators won't write a single line of code.

In this episode, Ghazi breaks down how he's building post-sales for the AI era, why he replaced CSMs with "product advocates," and what it looks like when your entire team builds their own tools — including their own version of Clari and a customer health dashboard, both built on Replit itself.

He also shares his take on the future of SaaS, how enterprises are quietly wrapping AI layers on top of Salesforce and Workday, and why Cursor, Claude, and OpenAI aren't keeping him up at night.

If you're in Customer Success, Revenue, or CS Ops, this episode will challenge how you think about your role.

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Timestamps

0:00 - Preview & Introduction

1:25 - Meet Ghazi Masood & Overview of Replit

4:40 - Building the GTM infrastructure

7:30 - How anyone at Replit can build internal tools

9:00 - Managing chaos when everyone becomes a creator

12:40 - Enterprise security & governance guardrails

15:47 - Are Cursor, Claude & OpenAI real competitors?

18:10 - Usage-based pricing explained

19:17 - Post-sales strategy for non-technical users

23:53 - Hiring 200 people in 12 months

24:40 - The future of SaaS

26:56 - SMBs replacing Workday and Tableau with Replit

30:40 - Lessons from Auth0 and Retool

32:32 - What Ghazi looks for when hiring

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What You’ll Learn

- What enterprise customers are quietly building on top of their existing SaaS tools — and what it means for vendors

- How SMBs are replacing Workday, Tableau, and traditional CRMs entirely by building on Replit

- How to handle churn when 90% of your users have zero technical background

- The governance and security guardrails that got Replit into financial services and government accounts

- How to structure a GTM catalog library so your team stops duplicating each other's work

- Ghazi's take on whether SaaS is dying — and why the answer is completely different depending on company size

- Why product passion matters more to Ghazi than years of sales experience when hiring

- How Replit thinks about competitive threats from Cursor, Claude Code and OpenAI — and why they're not losing sleep over any of them

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Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

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Where to Find Ghazi Masood

LinkedIn: https://www.linkedin.com/in/ghazi-masood-09195a2/

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Where to Find Josh:

LinkedIn: https://www.linkedin.com/in/jschachter/

Unchurned Substack: https://unchurned.substack.com/