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Is the future CSM a generalist empowered by specialist AI agents?

Live from Pulse Europe, Eleanora White, Global Head of CS & Solutions Architects at Supermetrics, joins Jenny Calvert to break down how her team is operationalizing Agentic AI inside customer success.

From internal AI agents that reduce friction…

To customer-facing automation at scale…

To autonomous agents that challenge and pressure-test insights…

Supermetrics is building a 3-phase AI roadmap that reshapes how CSMs work — without replacing the human relationship.

If you’re working on AI adoption or retention strategy — this episode is your blueprint.

---

Timestamps

0:00 - Preview & Introduction

0:40 - Meet Eleanora White

1:10 - AI as a Team Member

3:39 - Supermetrics’ 3-Phase AI Strategy

5:38 - Removing Friction with Internal AI

6:49 - The Future CSM Profile

9:00 - Hitting GRR Targets in Q4

11:03 - The “Stay-Alive” Retention Strategy

13:15 - Win-Back Metrics & LTV

14:27 - What’s Next for 2026

---

What You’ll Learn

* Why the best CSMs will become AI-powered generalists

* How to structure CS teams in the agentic era

* How Agentic AI can serve CSMs internally before customers

* The “stay-alive contract” retention strategy to increase long-term LTV

* How to win customers back without hurting GRR

* Why discovery is the most underrated CSM skill

---

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

---

Where to Find the Guests

Eleanora's LinkedIn: https://www.linkedin.com/in/eleanora-white/

---

Where to Find Jenny:

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

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Is community in B2B SaaS a cost center — or a growth engine hiding in plain sight?

In this episode of Unchurned, Josh Schachter sits down with Jon Wishart and community strategist Brian Oblinger to break down what community really means beyond vanity metrics and buzzwords.

They explore how community drives retention (GRR), expansion, and customer success — and why most companies are measuring it wrong. Plus, they unpack how AI is reshaping search, traffic, and discoverability, and why declining pageviews don’t mean declining value.

If you’re building, scaling, or rethinking your community strategy, this episode will change how you think about impact — and the future of customer connection.

---

Timestamps

0:00 - Preview & Introduction

1:45 - Meet Jon Wishart & Brian Oblinger

7:56 - What community in B2B SaaS actually is

9:00 - The “eras” of community ownership (Support → CS → Marketing → Product)

12:30 - Is community a cost center? And measuring impact

18:15 - The CFO conversation: investment vs expense

19:35 - AI, traffic declines, and community panic

21:30 - Why AI isn’t killing community

26:42 - The shift from “How do I?” to “How do we?”

30:40 - How community impacts feature development strategy

33:13 - Starting from zero: advice for new community builders

---

What You’ll Learn

* The core definition of community in B2B SaaS (without the fluff)

* How community drives retention, expansion, and lower support costs

* Why operational metrics (posts, members, pageviews) are outdated

* How to measure community’s business impact using cohort analysis

* What AI is really doing to search traffic and discoverability

* Why declining traffic doesn’t mean declining value

* How to future-proof your community strategy

* The fundamentals every new community leader must get right

---

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

---

Where to Find the Guests

Brian's LinkedIn: https://www.linkedin.com/in/jon-wishart/

Jon's LinkedIn: https://www.linkedin.com/in/jon-wishart/

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

18 months ago, venture capitalist Brett Queener made a bold prediction: 75% of customer-facing software companies would disappear. Now he’s back—with receipts.

On this episode of Unchurned, Brett explains why traditional SaaS moats have collapsed, why “system of record” is no longer defensible, and why we’ve entered a new era of agentic software—where you don’t buy tools anymore… You hire them.

Brett introduces what he calls the Judgment Layer—the only remaining defensible advantage in AI-powered products. In a world where agents can build, code, write, and self-organize, your job shifts from operator to manager. And your product’s job shifts from workflow engine to embedded judgment engine.

If you build, invest in, or buy software, this episode is required listening.

---

Timestamps

0:00 - Preview & Introduction

2:15 - From GPT moment to Agents

4:02 - Survival in the AI era

6:50 - Meet Brett

8:00 - Why SaaS moats disappeared

10:40 - The Judgment Layer explained & Feedback loops

13:58 - Hiring software vs. buying software

---

What You’ll Learn

* Why most SaaS companies are now replaceable

* Why embedded judgment is more valuable than workflow automation

* The new decision framework for buy vs. build

* Why the humanities may outperform pure STEM in the AI era

* What founders must build to remain defensible

---

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

---

Where to Find Brett Queener

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

Substack Article: https://queener.substack.com/p/in-the-end-it-may-just-be-judgement

Bonfire Ventures: https://www.bonfirevc.com/

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

What happens when you bring consumption-based customer success into a company?

In this episode of Unchurned, Jared Collins, Senior Director of Customer Success at Dell Technologies, shares how the Apex team is building a modern CS engine inside a $100B infrastructure giant.

Unlike SaaS companies that can deploy value instantly, Dell Apex operates in a world of physical logistics, supply chain constraints, and long hardware lead times. That means customer success isn’t just about adoption — it’s about anticipation.

Jared breaks down how his team connects data sources across the enterprise, builds trigger-based playbooks, partners deeply with sales, and prepares for an AI-driven future where customer signals surface before customers even recognize the need.

---

Timestamps

0:00 - Preview & Introduction

1:25 - Meet Jared Collins & Overview of Dell Apex

3:55 - The operational reality of shipping infrastructure

5:52 - Why CS must anticipate months ahead (lead times + forecasting)

8:20 - Working inside a $100B company: complexity vs opportunity

9:53 - Enabling CSMs for success to build strategic relationships

11:20 - Becoming data strategists: Building health scores across multiple business units

13:15 - Data → Triggers → Playbooks: the operational CS framework

16:46 - AI in CS: why foundations matter more than hype

19:20 - What success looks like for Apex CS in the next 1–2 years

21:55 - What Jared loves about Dell

---

What You’ll Learn

* Why hardware logistics fundamentally changes how CS operates

* How to build proactive CS using data triggers and standardized playbooks

* How to integrate CS inside a massive enterprise organization

* The difference between CapEx and consumption-based thinking

* Why AI only works if your data foundations are clean

* How to free CSMs to focus on strategic relationship-building

* What “good” looks like for CS inside infrastructure businesses

---

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

---

Where to Find Jared Collins

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

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Udi Ledergor joined Gong as employee #13 and marketer #1, helping build it from a 12-person startup to a category-defining revenue intelligence leader. As Chief Evangelist and author of "Courageous Marketing," he's learned one hard truth: if you don't have product-market-fit, no amount of marketing genius will save you.

In this conversation with Josh Schachter and Lauren Olerich, Udi shares the real indicators of product-market-fit, when companies should actually hire their first marketer, and how Gong evolved through multiple category iterations—from conversation intelligence to their current positioning as an AI operating system for revenue teams.

The discussion digs into Gong's "brand as person" exercise that created consistency across everything from content voice to event experiences, why data-driven content about salespeople cursing went viral, and the value of leaving raving fans everywhere you go. Udi's 27-year working relationship with Gong's CEO proves that burning bridges is career suicide in a small industry.

For anyone building brands, creating categories, or wondering if their startup is ready for marketing investment, this episode cuts through the fluff with practical frameworks and hard-won lessons.

---

Do you love great TV? Lauren co-hosts a podcast about popular TV show finales called The Finale Pod. Take a listen on Apple Podcasts, Spotify, or wherever you get your podcasts

---

Timestamps

0:00 - Preview & Introduction

0:54 - Meet Udi Ledergor and Lauren Olerich

4:00 - Udi's early journey at Gong

7:00 - When should you hire your first marketer?

10:55 - Lauren's early journey at Gainsight

14:00 - How Gong created the revenue intelligence category in 2019

22:58 - Diamond is forever

28:10 - Pulse predates Gainsight

32:17 - Early struggle at Gainsight

33:40 - The importance of domain expertise

41:52 - Brand as human: The exercise that creates consistency across everything

---

What You’ll Learn

* Evaluating product-market-fit for marketing to succeed

* How to create consistent tone across content, events, and category positioning

* Real tactics behind building and evolving categories across 10 years

* Why leaving raving fans at every company matters more than titles

* How a 27-year working relationship led to employee #13 becoming Chief Evangelist

* How data-driven content can go viral while staying perfectly on-brand

* When to publish the controversial insights your competitors are too afraid to share

---

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

---

Where to Find Udi Ledergor

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

Book "Courageous Marketing": https://www.udiledergor.com/book

Where to Find Lauren Olereich

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

The Finale Pod: Apple Podcasts⁠ | Spotify⁠

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Guy Galon, CCO at Obrela, joins Jenny Calvert at Pulse Europe in Dublin to discuss how he's transforming CS hiring and operations for the AI era.

In this conversation, Guy explains how he measures AI capability in his team, why he's building some AI tools internally at a cybersecurity company, and his three big bets for AI in 2026.

Guy tackles the generalist vs. specialist debate, explains why his technical background as a software engineer helped him earn credibility as a CS leader, and explores the emerging question: What does it mean to manage AI agents? From performance reviews for bots to getting CS leaders a real seat at the revenue forecasting table, this conversation covers the practical and philosophical challenges of leading customer success in 2026.

---

Timestamps

0:00 - Preview & Introduction

0:54 - Meet Guy Galon, CCO at Obrela

2:27 - The Generalist vs. Specialist Debate in the Age of AI

3:35 - The Multifaceted CSM Framework: Origins and Evolution

4:47 - How to Measure AI Proficiency

6:05 - 2026 AI Strategy

8:03 - What Changes When AI Delivers on These Three Promises

9:41 - Q4 Advice: Think in 8-10 Weeks, Not 12

11:30 - Getting CS a Seat at the Revenue Forecasting Table

13:00 - The Human Element AI Can't Replace: Trust and Influence

14:14 - The Future of Managing AI Agents

---

What You’ll Learn

* How the Multifaceted CSM Framework helps identify talent across five key capability areas

* How to balance AI innovation with data compliance in highly regulated industries like cybersecurity

* How to move CS from execution-focused roles to strategic contributors in revenue forecasting

* The difference between building internal AI capabilities vs. using external tools in customer success

* What it might look like to manage AI agents in the future (priorities, objectives, performance reviews)

---

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

---

Where to Find Guy Galon

LinkedIn: https://www.linkedin.com/in/guy-galon-b1a80/

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Christine Lavery, VP of Customer Success at Conga, shares why the traditional approach to digital customer success is broken and how she's applying digital motions across all customer tiers—not just the long tail.

Christine discusses her two major priorities for 2026: implementing product analytics as the foundation for customer outcomes and rolling out SMART goals to move from vague value conversations to measurable impact. She also explores how AI is transforming customer intelligence by synthesizing structured data (product analytics) with unstructured data (emails, support tickets, NPS verbatims) to create a complete picture of customer health.

---

Timestamps

0:00 - Preview & Introduction

1:25 - Meet Christine Lavery

2:15 - Overview of Conga

3:05 - Conga's acquisition of PROS and the future of CPQ

4:04 - Structure of Christine's 100-person global CS organization

6:35 - Why digital motions shouldn't be "long tail only."

9:52 - Mapping customer journeys and communication strategies

13:42 - Collaboration between CS, Product, and Marketing

19:42 - Reporting to revenue and driving growth

25:30 - Breaking down the SMART goals framework for customer outcomes

27:42 - How AI fits into product analytics and customer intelligence

31:27 - Why CS leaders must fight for a seat at the table

---

What You’ll Learn

* Why limiting digital customer success motions to only "long tail" customers is a mistake

* How to scale one-to-many strategies across enterprise and strategic accounts

* How to use SMART goals to transform vague "value" conversations into measurable customer outcomes that clearly demonstrate ROI

* The difference between basic product analytics and sophisticated use-case tracking that helps you coach customers to better outcomes

* How AI synthesizes structured data (product usage) and unstructured data (emails, support tickets, NPS) to create a complete picture of customer health

* Why CS leaders must actively fight for a seat at the executive table

---

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

---

Where to Find Christine Lavery

LinkedIn: https://www.linkedin.com/in/christine-lavery/

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

Jim Richmond is the Chief Customer Officer at Smartling, an AI-powered translation company doing AI "before it was cool" since 2009. Leading 50 professionals across support, services, and customer success, Jim shares his 2026 playbook: why GRR is his North Star, how he's building systems to scale 4x, and why role specialization beats generalization in the AI era.

Jim reveals how AI bots eliminated single-touch support tickets at Smartling, why he still carries his own book of business as a CCO, and his career advice for aspiring leaders to build the professional empathy that makes them an authentic partner.

---

Timestamps

0:00 - Preview & Introduction

1:25 - Meet Jim Richmond

1:50 - Smartling Overview

4:33 - 2026 Priorities: GRR as the North Star metric

6:30 - Building a four-quarter forecast

9:40 - Building systems for 4x growth

12:24 - Forecasting to eliminate surprises

14:55 - Will AI make CSMs more generalized or specialized?

18:32 - How AI bots eliminated single-touch support tickets

21:42 - What it's like being a first-time Chief Customer Officer

23:38 - The rule of thirds: How a CCO allocates time

25:10 - Why this CCO still carries his own book of business

25:52 - Seek out a diversity of experiences

---

What You’ll Learn

* How to build a four-quarter forecast that eliminates revenue surprises

* Why role specialization creates more operational leverage than generalization

* How AI bots eliminated single-touch support tickets at Smartling

* Why leading from the front means carrying your own book of business

* How to build professional empathy by seeking diverse experiences across sales, CS, and services

---

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

---

Where to Find Jim Richmond

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

---

Where to Find Josh:

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

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

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

GitHub's SVP of Customer Success Abbas Haider Ali reveals why post-sales investment should drop from 10% to 7% of revenue, breaks down the 6-layer customer health model used by Fortune 100 companies, and introduces the "specialized generalist"—the AI-native CSM role that's redefining customer success in 2026. Learn the frameworks CS leaders need to prove ROI, restructure teams, and solve the 80-20 problem in AI adoption.

From playbook evolution to knowledge management, this conversation offers a practical roadmap for CS leaders navigating rapid technological change while proving ROI to increasingly demanding CFOs. Whether you're structuring your CS organization, defending your budget, or preparing your team for AI transformation, this episode delivers the frameworks and benchmarks you need.

---

Timestamps

0:00 - Preview & Introduction

2:05 - Meet Abbas Haider Ali & GitHub's Scale

3:40 - The 500-Pound Zoom Background Story

8:40 - The Customer Hierarchy of Needs Framework

17:50 - Why CS Playbooks Must Constantly Evolve

21:00 - How Abbas Discovered the CS Budget Benchmark (Surveying 100+ Companies on Post-Sales Investment)

25:50 - The Journey from 10% to 7%: AI's Impact on Post-Sales Economics

27:40 - Should You Aim for 7% or 10%?

28:58 - CFO Reactions & Proving ROI in a Post-ZIRP World

33:33 - Under-Investing vs. Over-Investing in Support

38:05 - Return on the 10% - 7% Investment

46:46 - Introducing the "Specialized Generalist" CSM Role

51:27 - Why AI-Native Organizations Scale Faster

53:00 - Abbas's 2026 CS Resolution

---

What You’ll Learn

* Why post-sales investment should be 7% of revenue and how AI is driving this shift

* The ROI framework CS leaders need to defend their budgets to CFOs in a capital-constrained environment

* Why customer health models need constant evolution (not static playbooks)

* Why specialist roles will move up the value chain in AI-powered organizations

* The T-chart model for CSM skills with AI proficiency as the critical vertical capability

* Why CS leaders should come from multidisciplinary backgrounds (product, engineering, sales)

---

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

---

Where to Find Abbas Haider Ali:

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

---

Where to Find Josh:

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

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

---

Resources Mentioned:

- CS operating model

- ROI of Customer Success (original)

- ROI of Customer Success (updated)

- Rise of the Specialized Generalist

- The future of CSMs is more generalized

Ready to churn less and win more? 🏆 Subscribe for a simple, once-a-month rundown of the episodes at gainsight.com/unchurned

What if the fastest path to product-market fit isn't building more features—it's deploying engineers to solve customer problems?

Diego Ballona, Senior Director of Engineering at Intercom, runs Forward Deployed Engineering—a team that helped scale Fin from 5 design partners to 7,000 customers, hitting a 67% resolution rate in 18 months. But FDE isn't professional services rebranded. It's product managers, engineers, and data scientists working directly with customers to accelerate outcomes and turn real friction into features everyone can use.

Diego breaks down the exact team structure that makes this work, why outcome-based pricing changes go-to-market strategy, and how to know if FDE is right for your business. If you're scaling an AI product or rethinking how engineering and CS collaborate, this conversation delivers the blueprint.

---

Timestamps

0:00 - Preview & Introduction

3:00 - Diego's origin story at Intercom and how FDE emerged organically

5:35 - Intercom's scale: 7,000 Fin customers, 67% average resolution rate across all segments

7:25 - From 5 design partners to proving the FDE model

9:12 - Building the business case and getting leadership buy-in

12:05 - FDE team structure

18:55 - How FDE turns customer insights into product features

23:15 - Ownership boundaries: CSMs vs. FDE teams

25:25 - Outcome-based pricing and why it aligns incentives perfectly

27:00 - Diego's golden nugget: Stay open-minded

---

What You’ll Learn

* How Intercom scaled from 5 design partners to 7,000 Fin customers in 18 months using Forward Deployed Engineering

* Why the FDE team structure requires three specific roles working together

* How outcome-based pricing changes everything about go-to-market incentives, comp plans, and team alignment

* Why FDE engineers need different skills from product engineers

* How to know if FDE is right for your business (and why it might not be)

* The ownership boundaries between FDE teams and CSMs that make cross-functional collaboration actually work

---

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

---

Where to Find Diego:

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

Intercom: https://www.intercom.com

Fin AI Agent: https://www.intercom.com/fin

---

Where to Find Josh:

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

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