Insights Unlocked Episode Summary
Episode Title: From SaaS to Retention as a Service: How AI is Changing Customer Success
Date: May 11, 2026
Host: Nathan Isaacs (Principal Content Marketing Manager, UserTesting)
Guest: Josh Schachter (SVP of Strategy & Go-To-Market at Gainsight, Host of Unchurned Podcast)
Episode Overview
This episode explores how AI is rapidly transforming the practice of customer success—from scaling interactions and capturing feedback to defining new models like "retention as a service" (RAS). Nathan Isaacs and guest Josh Schachter unpack what leading teams are doing to drive outcomes and loyalty, why relationships (not just technology) matter more than ever, and how companies can avoid common pitfalls as they build agentic workflows. The conversation dives deep into customer feedback, AI-powered workflows, actionable advice, and key lessons from dozens of customer success leaders and innovators.
Guest Introduction & Background
[01:14]
Nathan introduces Josh Schachter, who shares his unexpected journey into customer success, having started in product management and working with startups and at Boston Consulting Group before finding his calling through his own company, Update AI.
- Key Quote:
"I didn't know what customer success was five years ago...we followed the breadcrumb trail and we came across this thing called customer success. And we said, oh, wow, this group, like, this is who we want to serve as our early beachhead." (Josh Schachter, [01:27])
The Relational Founder and Building Relationships
[03:16]
Josh discusses his upcoming book, "The Relational Founder," which focuses on founders who excel through relationship-building—with themselves, teams, co-founders, investors, and communities.
-
Key Points:
- Building genuine relationships as a superpower in business
- Authenticity and intentionality are essential for effective relationship-building
- Personal anecdote: Overcoming his fear of public speaking to build a personal brand and community presence
-
Notable Quote:
"It's uncomfortable for us to take compliments, right, to listen to those out loud. But, but I'll take it because it's something I'm actually pretty passionate about is building relationships." (Josh, [05:36])
Customer Success Best Practices & AI Transformation
Customer Success is Not One-Size-Fits-All
[09:37]
Josh explains that while every customer success (CS) program is unique, leading teams share common tactics—especially in leveraging AI and listening to the voice of the customer.
- Key Insights:
- Unlike sales, CS lacks universal playbooks; approaches must be tailored.
- The evolution from SaaS (Software as a Service) to RAS (Retention as a Service) is redefining the post-sales organization to focus on measurable outcomes and retention.
Segmentation & Scalable AI in CS
[10:11]
-
CS programs are segmented by customer profile:
- High-touch, strategic accounts: Human-led, relationship-focused
- Long-tail: Increasing use of autonomous AI (e.g., Gainsight’s ATLAS agent for automated renewals and scalable feedback collection)
- Mid-tier/pooled: Digital touchpoints (community, education, etc.)
-
AI Use Case:
"ATLAS is a way to autonomously have email and phone exchanges with your customers at the long tail as they come up for renewal....Now you're able to have the bots and agents help you manage that end to end." (Josh, [12:05])
-
Synthesizing Feedback at Scale:
Automated feedback collection from every long-tail interaction, allowing teams to detect sentiment and trends previously impossible to capture.
Value Conversations & AI-Driven Workflows
[13:34]
In high-touch segments, AI helps teams generate value narratives and QBR/EBR decks—demonstrating how goals have evolved, mapping value delivered, and identifying where customers are underutilizing entitlements.
- Initiative Example:
Gainsight's "instance reviews," powered by automated analysis of client configurations, helps CSMs articulate value, gaps, and opportunities for customers with minimum manual work.
[15:39]
Advice for Building Agentic Workflows
Overcoming Challenges & Org Change Management
[19:13]
-
Overlay voice of the customer on service design maps to prioritize automations
-
Find champions in the organization—not always the most technical, but the most curious and motivated—and give them the space to innovate
-
Notable Story:
Josh recounts how clearing one ops team member’s calendar enabled rapid, transformative progress in building out CS automation ([20:23]).
AI Product "Retention Apocalypse" & Product Marketing
[22:07]
Discussion of high churn rates among AI SaaS tools and how companies are managing through consolidation and product-market fit challenges.
- Key Quote:
"A really important driver of retention and sales in this age is your product marketing. Because when all the products feel kind of similar...can you get the message of your value prop across effectively?" (Josh, [23:14])
What Top Customer Success Leaders Do Differently
[24:34]
- CS leaders all grapple with embracing AI and feel they're playing catch-up—however, most are actually ahead.
- Success comes from:
- Assigning dedicated roles/talent to AI experimentation and implementation
- Leading by example (at Gainsight, even the CEO is a top AI user and "vibe-coder")
- Spotting and promoting grassroots innovators
[27:13]
- The future of CS roles: As AI handles documentation and note-taking, CSMs are becoming "value architects," focusing on meaningful, consultative conversations that feed quality input into automation.
- Debate on whether CSMs will become more like generalists or specialists as roles evolve
Practical Advice for Cross-Functional Product Teams
[29:53]
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Don’t oversell; prioritize product-customer fit from the beginning
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Create tight feedback loops between CS, product, and design: capture requests, close the feedback loop when improvements are made, and communicate those changes directly to customers
-
Small wins matter:
In the AI era, small fixes requested by customers are easier to deliver—these quick wins boost perceived value and foster loyalty.
-
Notable Anecdote:
Josh shares the example of giving Notion feedback and seeing it implemented—illustrates the impact of quick action on customer delight ([32:17])
Closing & Resources
[33:16]
- Connect with Josh on LinkedIn (he’s highly active)
- Listen to the Unchurned podcast and check out the Substack at unchurned.gainsight.com for deep, behind-the-scenes thought leadership on post-sales and CS
- Bonus: Josh’s content gets a testimonial from Nathan for being actionable and valuable even outside CS circles
Key Quotes & Timestamps
- "I didn't know what customer success was five years ago...we wanted to serve this group as our early beachhead." (Josh, [01:27])
- "There's this movement from SaaS to RAS—retention as a service. Everything that we do post-sales is going to be incredibly outcome-driven." (Josh, [10:11])
- "ATLAS is a way to autonomously have email exchanges and phone call exchanges with your customers at the long tail as they come up for renewal." (Josh, [12:05])
- "You've got to create a blueprint for the workflow that you're trying to AI-ify or identify." (Josh, [17:41])
- "A really important driver of retention and sales in this age is your product marketing." (Josh, [23:14])
- "The folks that have been successful have also led by example themselves—at the leadership level." (Josh, [25:08])
- "As AI can do the note-taking and all that stuff, it becomes the role of CSMs in these conversations to get the best stuff out of the conversation to feed the AI." (Josh, [27:38])
- "Don’t oversell; sell products where the customer is a good fit for the product, not oversell. That's the foundation." (Josh, [29:53])
- "When I hear and I see those little things [requested features] added, I'm, I feel like they're appreciating what my problems are on a day to day basis." (Nathan, [31:37])
Timestamps for Important Segments
- [01:14] – Josh’s background and journey into customer success
- [03:16] – The relational founder, building relationships, and authentic leadership
- [09:37] – What leading customer success teams do differently; the evolution to RAS
- [10:11] – Customer segmentation strategies and AI in CS (ATLAS agent)
- [13:34] – Value conversations: AI-generated reports and customer touchpoints
- [15:39] – Building agentic workflows: Practical tips and pitfalls
- [19:13] – Mapping service design to voice of the customer
- [22:07] – AI product churn ("retention apocalypse") and the importance of product marketing
- [24:34] – Common threads among top CS leaders in the AI era
- [29:53] – Advice for cross-functional teams: feedback loops and acting on customer insights
Memorable Moments
- Josh’s description of overcoming stage fright—contrasting his past with his current prominence as a podcast host and thought leader ([07:14])
- The power of quick, AI-enabled responses to customer requests for even the smallest product changes ([32:17])
- Anecdotes about building personal and professional relationships that outlast any single startup or product
Summary Takeaways
- AI is revolutionizing customer success but layered, authentic human relationships and strong cross-team communication remain central.
- Retention as a Service (RAS) is the new standard—outcomes and loyalty trump basic subscription sales.
- Agentic workflows powered by AI free up human teams for more value-driven work, but require careful, intentional design and data hygiene.
- Product marketing and tight feedback loops are essential in an environment where AI products proliferate and differentiation is challenging.
- Leaders must empower curious, motivated individuals to build, experiment, and share successes across teams.
- Actionable advice for all: Don’t oversell, close the feedback loop, and use AI to amplify—rather than replace—meaningful human connections.
For more:
- Check out the Unchurned podcast
- Read Unchurned Substack at unchurned.gainsight.com
- Connect with Josh on LinkedIn
This summary skips advertisements, show intros/outros, and focuses on rich content and insights from the episode.