AI Customer Success Brief Transistor (https://transistor.fm) https://feeds.transistor.fm/ai-customer-success-brief 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. © 2026 Infinite Renewals ed04661f-8e26-5737-b2a2-6bf584517ea0 yes en Fri, 14 Aug 2026 12:07:23 -0400 Fri, 14 Aug 2026 12:08:25 -0400 https://infiniterenewals.com/ https://img.transistorcdn.com/ZvO2WwLDnzX_wHpL7sbvgwjHdDGjrqbn6zkD5EE6GAQ/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9iZGMz/YWZiNzVhMDk3ZTIx/ZDc0NTQzMTNjMDc1/ODkyYS5wbmc.jpg AI Customer Success Brief https://infiniterenewals.com/ episodic Jeff Kushmerek 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. What operators are actually building with AI in customer success -- past the prototype and into production. customer success, AI, post-sales, CS operations, AI agents, customer success management, HubSpot, Salesforce, RevOps, automation, SaaS, CCO, customer lifecycle, AI implementation, post-sales AI Jeff Kushmerek No No The Claude Skill That Killed 8 Hours of Account Planning Prep | Ejieme Eromosele 4 4 The Claude Skill That Killed 8 Hours of Account Planning Prep | Ejieme Eromosele full 6668b1c6-27ac-4ff9-920c-a12219748d00 https://share.transistor.fm/s/7ac3d2d1 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 one
The external research gap that nobody had time for, and why walking into an expansion conversation without it goes badly
Why she built a skill rather than a project or a saved prompt, and what that fixed about consistency across the team
The seven inputs feeding the plan, including contract terms, call recordings, CRM notes, and deep research
Why one step in the workflow hands off to Gemini instead of staying in Claude
How she got it through her own InfoSec review before turning it on for everyone
What 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 minutes
00:15 Why enterprise accounts are the hardest to plan
02:35 The problem she set out to solve
05:08 The process that already existed
05:50 Why she built it as a Claude skill
07:03 The seven inputs that feed the plan
08:17 Six systems, eight to ten hours
09:11 Prototyping it herself
10:17 Handing one step to a different model
11:00 Getting it through InfoSec
13:21 What changed
14:55 The economics
16:22 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

]]> 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 one
The external research gap that nobody had time for, and why walking into an expansion conversation without it goes badly
Why she built a skill rather than a project or a saved prompt, and what that fixed about consistency across the team
The seven inputs feeding the plan, including contract terms, call recordings, CRM notes, and deep research
Why one step in the workflow hands off to Gemini instead of staying in Claude
How she got it through her own InfoSec review before turning it on for everyone
What 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 minutes
00:15 Why enterprise accounts are the hardest to plan
02:35 The problem she set out to solve
05:08 The process that already existed
05:50 Why she built it as a Claude skill
07:03 The seven inputs that feed the plan
08:17 Six systems, eight to ten hours
09:11 Prototyping it herself
10:17 Handing one step to a different model
11:00 Getting it through InfoSec
13:21 What changed
14:55 The economics
16:22 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

]]> Fri, 14 Aug 2026 12:06:54 -0400 Jeff Kushmerek Jeff Kushmerek 996 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 one
The external research gap that nobody had time for, and why walking into an expansion conversation without it goes badly
Why she built a skill rather than a project or a saved prompt, and what that fixed about consistency across the team
The seven inputs feeding the plan, including contract terms, call recordings, CRM notes, and deep research
Why one step in the workflow hands off to Gemini instead of staying in Claude
How she got it through her own InfoSec review before turning it on for everyone
What 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 minutes
00:15 Why enterprise accounts are the hardest to plan
02:35 The problem she set out to solve
05:08 The process that already existed
05:50 Why she built it as a Claude skill
07:03 The seven inputs that feed the plan
08:17 Six systems, eight to ten hours
09:11 Prototyping it herself
10:17 Handing one step to a different model
11:00 Getting it through InfoSec
13:21 What changed
14:55 The economics
16:22 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

]]> customer success, AI, post-sales, CS operations, AI agents, customer success management, HubSpot, Salesforce, RevOps, automation, SaaS, CCO, customer lifecycle, AI implementation, post-sales AI No He Replaced the Health Score With a Renewal Probability Tool | Sean Reid, Supermetrics 3 3 He Replaced the Health Score With a Renewal Probability Tool | Sean Reid, Supermetrics full 5eaea8a6-ff9c-4e9d-aced-1ded4d9754c8 https://share.transistor.fm/s/9fd05051 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

]]> 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

]]> Tue, 04 Aug 2026 18:04:16 -0400 Jeff Kushmerek Jeff Kushmerek 1132 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

]]> customer success, AI, post-sales, CS operations, AI agents, customer success management, HubSpot, Salesforce, RevOps, automation, SaaS, CCO, customer lifecycle, AI implementation, post-sales AI No We Replaced Gainsight in 60 Days and Built Our Own CS Platform | Ashley Stallings, Salsify 2 2 We Replaced Gainsight in 60 Days and Built Our Own CS Platform | Ashley Stallings, Salsify full 2d10adce-ac45-4430-9d57-7178f7ce8175 https://share.transistor.fm/s/dfc1f1b2 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 decision
How VIP was built on Replit and what it actually does for CSMs
The internal governance model: how AI projects get submitted, reviewed, and prioritized
Build vs. buy: the real argument CSP vendors make and why it's a false choice
What "handing it to a qualified team" actually means -- CICD, VPNs, data access controls
Health score problems: why they rebuilt from scratch and moved to segment and industry-specific scoring
Variance data as the new leading indicator -- top movers, not static red/yellow/green
The CSM cockpit vision: telling reps where to focus instead of letting them default to whoever's loudest
What they lost during the migration and how they're getting it back
The 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

]]> 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 decision
How VIP was built on Replit and what it actually does for CSMs
The internal governance model: how AI projects get submitted, reviewed, and prioritized
Build vs. buy: the real argument CSP vendors make and why it's a false choice
What "handing it to a qualified team" actually means -- CICD, VPNs, data access controls
Health score problems: why they rebuilt from scratch and moved to segment and industry-specific scoring
Variance data as the new leading indicator -- top movers, not static red/yellow/green
The CSM cockpit vision: telling reps where to focus instead of letting them default to whoever's loudest
What they lost during the migration and how they're getting it back
The 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

]]> Wed, 08 Jul 2026 06:54:43 -0400 Jeff Kushmerek Jeff Kushmerek 962 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 decision
How VIP was built on Replit and what it actually does for CSMs
The internal governance model: how AI projects get submitted, reviewed, and prioritized
Build vs. buy: the real argument CSP vendors make and why it's a false choice
What "handing it to a qualified team" actually means -- CICD, VPNs, data access controls
Health score problems: why they rebuilt from scratch and moved to segment and industry-specific scoring
Variance data as the new leading indicator -- top movers, not static red/yellow/green
The CSM cockpit vision: telling reps where to focus instead of letting them default to whoever's loudest
What they lost during the migration and how they're getting it back
The 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

]]> customer success, AI, post-sales, CS operations, AI agents, customer success management, HubSpot, Salesforce, RevOps, automation, SaaS, CCO, customer lifecycle, AI implementation, post-sales AI No Why Most AI in Customer Success Stays on a Laptop | AI Customer Success Brief Ep. 1 1 1 Why Most AI in Customer Success Stays on a Laptop | AI Customer Success Brief Ep. 1 full 74c13d9b-4d3b-4eb4-80d5-78abb4b62dc8 https://share.transistor.fm/s/8633d160 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 move
  • Mapping AI to the customer lifecycle: onboarding, adoption, renewal, expansion
  • The MCP path vs. the enterprise app path
  • Real deployment architecture: GitHub Actions, Azure, Entra SSO, Tailscale VPN
  • Why Intercom's help desk is a problem and what we built around it

About 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.

]]> 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 move
  • Mapping AI to the customer lifecycle: onboarding, adoption, renewal, expansion
  • The MCP path vs. the enterprise app path
  • Real deployment architecture: GitHub Actions, Azure, Entra SSO, Tailscale VPN
  • Why Intercom's help desk is a problem and what we built around it

About 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.

]]> Wed, 24 Jun 2026 15:27:53 -0400 Jeff Kushmerek Jeff Kushmerek 955 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 move
  • Mapping AI to the customer lifecycle: onboarding, adoption, renewal, expansion
  • The MCP path vs. the enterprise app path
  • Real deployment architecture: GitHub Actions, Azure, Entra SSO, Tailscale VPN
  • Why Intercom's help desk is a problem and what we built around it

About 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.

]]> customer success, AI, post-sales, CS operations, AI agents, customer success management, HubSpot, Salesforce, RevOps, automation, SaaS, CCO, customer lifecycle, AI implementation, post-sales AI No