AI Customer Success Brief

Jeff Kushmerek
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What operators are actually building with AI in customer success -- past the prototype and into production. Each episode covers a real implementation: the problem, what got built, and how it got deployed. No vendor pitches, no roadmap theater. CS leaders, CCOs, and post-sales operators talking about what's running on their teams right now. Hosted by Jeff Kushmerek, founder of Infinite Renewals. 25 years in CS and professional services. Sponsored by Infinite Renewals.

Episodes

  1. Aug 14

    The Claude Skill That Killed 8 Hours of Account Planning Prep | Ejieme Eromosele

    Ejieme Eromosele took enterprise account planning prep from eight to ten hours down to fifteen minutes by building a structured Claude skill. The reason it worked that fast is the part most teams skip: she had been running a real account planning process manually for years before any AI touched it. She knew what a finished plan had to contain. She knew where the prep time was going. She knew which account managers were doing the thorough version and which ones were not. The skill just compressed something that already existed. In this episode: Why account plans were taking eight to ten hours, and the six systems the team was pulling from to build oneThe external research gap that nobody had time for, and why walking into an expansion conversation without it goes badlyWhy she built a skill rather than a project or a saved prompt, and what that fixed about consistency across the teamThe seven inputs feeding the plan, including contract terms, call recordings, CRM notes, and deep researchWhy one step in the workflow hands off to Gemini instead of staying in ClaudeHow she got it through her own InfoSec review before turning it on for everyoneWhat the fifteen minutes actually buys, and the honest version of the economics ABOUT EJIEME EROMOSELE Ejieme Eromosele is an award-winning Customer Success and Revenue executive and an AI in Customer Experience advisor, guiding hundreds of enterprises on AI strategy and deploying AI solutions across customer journeys. She has built and scaled post-sales functions from the ground up, including as a company's first VP of Customer Success and Account Management and as GM of an international expansion. Earlier in her career she built The New York Times' first formal Customer Experience function, proving the link between customer satisfaction and subscriber retention and earning the NYT Publisher's Award. She also spent a decade in management consulting at PwC and Accenture. Ejieme is the founder of Success in Black, a global community of 5,000 members advancing Black talent in tech and Customer Success, and co-author of The Customer Success Talent Playbook. She serves as a board member, advisor, and angel investor to early-stage startups. She holds a BA in Economics and an MBA in Strategy and Global Business, both from NYU. Connect with Ejieme: https://www.linkedin.com/in/ejieme/ CHAPTERS 00:00 Eight hours to fifteen minutes00:15 Why enterprise accounts are the hardest to plan02:35 The problem she set out to solve05:08 The process that already existed05:50 Why she built it as a Claude skill07:03 The seven inputs that feed the plan08:17 Six systems, eight to ten hours09:11 Prototyping it herself10:17 Handing one step to a different model11:00 Getting it through InfoSec13:21 What changed14:55 The economics16:22 Why the sequence matters ABOUT THE SHOW The AI Customer Success Brief is for post-sales operators past the prototype stage. Every episode is about somebody who built something their team actually uses, not a demo that lives in a chat window. Hosted by Jeff Kushmerek, founder of Infinite Renewals and author of Retention Starts in Implementation. Subscribe for new episodes. WORK WITH US Not sure where your team actually stands on AI? Take the free AI Readiness assessment. Ten questions, and you get a readiness tier and an action plan based on the Infinite Renewals AI Capability Maturity Model. Built something your CS team uses every day? Come on the show. https://calendly.com/infiniterenewals/ai-cs-brief-recording Jeff Kushmerek on LinkedIn: https://www.linkedin.com/in/jeffkushmerek/Infinite Renewals: https://infiniterenewals.com

    The Claude Skill That Killed 8 Hours of Account Planning Prep | Ejieme Eromosele

  2. Aug 4

    He Replaced the Health Score With a Renewal Probability Tool | Sean Reid, Supermetrics

    Sean Reid runs customer success for EMEA and JAPAC at Supermetrics. He went back through the churn on his install base and found that sixty-two percent of it was avoidable, with signals present weeks before anyone acted. The health score that was supposed to catch it spoke a language only the CS team understood, so he removed it and built a renewal probability in its place. This episode covers the sequence he followed, which is the part most teams skip. He answered two process questions before he opened a single vendor conversation: how do you get CSMs thinking about risk from day zero instead of day minus ninety, and how do you show every other department that the work they do moves the renewal. Then he built the score with Claude as the working partner and weighted it forty percent system, sixty percent human, which is close to the inverse of how most vendor health scores are built. We also get into his definition of the agentic CSM, which is a CSM managing agents that handle transactional work rather than a CSM who uses AI to write emails. Chapters: 00:00 Sixty-two percent of the churn was avoidable 0X:XX Why health scores stopped moving anyone outside CS 0X:XX The two questions Sean answered before building 0X:XX Renaming the score to renewal probability 0X:XX The 40/60 split and why the human side is larger 0X:XX What changed across legal, product, and leadership 0X:XX Defining the agentic CSM The AI Customer Success Brief is produced by Infinite Renewals. We help PE-backed SaaS companies build AI into post-sales operations, starting with the process work that has to happen before anything gets deployed. Find out where your CS team actually stands. Ten questions, two minutes, and you get a readiness tier and an action plan: https://info.infiniterenewals.com/cs-ai-assessment Work with us: https://www.infiniterenewals.com Come on the show: https://calendly.com/infiniterenewals/ai-cs-brief-recording Jeff Kushmerek on LinkedIn: https://www.linkedin.com/in/jeffkushmerek/ Sean Reid on LinkedIn: https://www.linkedin.com/in/sean-reid/ Subscribe for new episodes on what post-sales teams are actually running in production. #CustomerSuccess #AI #SaaS #RevenueOperations #CustomerRetention

  3. Jul 8

    We Replaced Gainsight in 60 Days and Built Our Own CS Platform | Ashley Stallings, Salsify

    Ashley Stallings at Salsify made a call most CS leaders won't: when their Gainsight renewal came up, they didn't shop for a replacement. They built one. In two months, her team migrated off Gainsight and into an internal platform called VIP (Value Intelligence Platform), built on Replit. It runs a Salsify-built LLM that pulls product usage, industry data, case studies, and pitch context into a single account view for every CSM.This is what a well-governed, engineering-backed AI build actually looks like in production -- including the parts that didn't go smoothly. Topics covered: Why Salsify replaced Gainsight in two months and what forced the decisionHow VIP was built on Replit and what it actually does for CSMsThe internal governance model: how AI projects get submitted, reviewed, and prioritizedBuild vs. buy: the real argument CSP vendors make and why it's a false choiceWhat "handing it to a qualified team" actually means -- CICD, VPNs, data access controlsHealth score problems: why they rebuilt from scratch and moved to segment and industry-specific scoringVariance data as the new leading indicator -- top movers, not static red/yellow/greenThe CSM cockpit vision: telling reps where to focus instead of letting them default to whoever's loudestWhat they lost during the migration and how they're getting it backThe hackathon that produced a cohort-based outreach tool -- built by CSMs, not engineers customer success, AI customer success, Gainsight alternative, build vs buy, CSP replacement, Salsify, post-sales AI, customer success platform, CS operations, AI in SaaS, HubSpot customer success, health score, CSM tools, post-sales operations, Infinite Renewals Jeff Kushmerek is the founder of Infinite Renewals and the author of Retention Starts in Implementation. 🎙️ AI Customer Success Brief is sponsored by Infinite Renewals.📩 Find Jeff on LinkedIn: linkedin.com/in/jeffkushmerek🌐 infiniterenewals.com

    We Replaced Gainsight in 60 Days and Built Our Own CS Platform | Ashley Stallings, Salsify

  4. Jun 24

    Why Most AI in Customer Success Stays on a Laptop | AI Customer Success Brief Ep. 1

    Episode 1: AI in Post-Sales — Prototyping to Production Most AI in customer success never makes it off someone's laptop. This episode is about why, and what it actually takes to get something running in production. Jeff covers the mistake most CS teams make when they start thinking about AI, what the customer lifecycle looks like when you map it to real pain points, and the fork most operators don't know they're at: when MCP is enough vs. when you're building an actual application whether you planned to or not. Real example included: a prototype built in Claude that became a containerized app running on Azure behind Tailscale VPN and Entra SSO — because the data lived in two systems that no MCP could bridge. No metrics yet for most of this. That's fine. Sometimes the win is just getting parity — your internal systems wired together, working the way your team actually needs them to. What's covered: Why starting with the tool is the wrong moveMapping AI to the customer lifecycle: onboarding, adoption, renewal, expansionThe MCP path vs. the enterprise app pathReal deployment architecture: GitHub Actions, Azure, Entra SSO, Tailscale VPNWhy Intercom's help desk is a problem and what we built around itAbout the show: The AI Customer Success Brief is for operators past the prototype stage. Real implementations, real deployment paths, no vendor pitches. Hosted by Jeff Kushmerek, founder of Infinite Renewals. Sponsored by Infinite Renewals.

    Why Most AI in Customer Success Stays on a Laptop | AI Customer Success Brief Ep. 1
  • 4 Episodes

About

What operators are actually building with AI in customer success -- past the prototype and into production. Each episode covers a real implementation: the problem, what got built, and how it got deployed. No vendor pitches, no roadmap theater. CS leaders, CCOs, and post-sales operators talking about what's running on their teams right now. Hosted by Jeff Kushmerek, founder of Infinite Renewals. 25 years in CS and professional services. Sponsored by Infinite Renewals.

Information

  • Creator
    Jeff Kushmerek
  • Years Active
    2026
  • Episodes
    4
  • Rating
    Clean
  • Copyright
    © 2026 Infinite Renewals
  • Show Website
    AI Customer Success Brief