How Documentation Became a Bottleneck and Solution

When Cloudbeds faced a post-sales organization at 120% capacity, no budget, and declining efficiency, Colin Slade chose to rebuild the operation through AI. Within nine months, his four-person AIOps team deployed more than 150 workflows and agents, automating 75% of repetitive work and reclaiming 7,000 hours every month.

This episode details how Colin turned a resource-starved customer success organization into an AI-driven engine. It explores the early missteps, the shift from overengineering to small, quick wins, and how incremental adoption evolved into company-wide transformation.

A practical study in applied AI, organizational change, and measurable outcomes—showing how constraint, not abundance, can drive real innovation.

Timestamps

0:00 – Preview & Introduction

0:57 – Meet Colin Slade and the Situation at Cloudbeds

9:25 – Mitigating Team Fears Around AI Replacing Jobs

13:13 – The Stepwise Approach to Implementing AI

19:50 – Scaling Securely: Working with IT, Risk-Taking, and Adoption

24:00 – Roles and Team Structure for Effective AI Operations

33:10 – Documentation as a Hidden Bottleneck

39:45 – Build vs. Buy: Why Cloudbeds Built In-House

42:20 – The Impact and a Culture of Fearless Experimentation

What You’ll Learn

* How to rebuild a post-sales org around AI without additional headcount

* The step-by-step approach to deploying 150+ workflows in under a year

* How to identify and structure AI roles: visionary, operators, knowledge masters, and project leads

* The cultural and psychological levers for AI adoption

* How to optimize documentation for AI readability (and boost SEO at the same time)

* The measurable impact of AI on cost savings, efficiency, and morale

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Check out the Key Takeaways & Transcripts: ⁠https://www.gainsight.com/presents/series/unchurned/⁠

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Where to Find Colin:

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

Where to Find Josh:

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

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Resources:

n8n – https://n8n.io/

Forethought – https://forethought.ai/

Google AI Studio – https://aistudio.google.com/

Anthropic Claude – https://claude.ai/

Gemini – https://gemini.google.com/app

Lovable – https://lovable.dev/

Pinecone – https://www.pinecone.io/

Snowflake – https://www.snowflake.com/en/

Zendesk – https://www.zendesk.nl/

Salesforce – https://www.salesforce.com/

Slack – https://slack.com/