Automation as Core Strategy: Aarin Bailey on RPA, AI, and Scaling MSP Operations

On the Evolved Radio podcast, Todd interviews Aarin Bailey, COO at Webit Services and former COO at MSP Bots, about treating automation as a core MSP operating strategy.

Aarin describes how his automation focus accelerated around COVID by chaining PowerShell scripts, later expanding into Python, GUIs, and modular systems connected via RESTful APIs, with much of the computation running outside the RMM on servers (including SQL and Python) while the RMM remains mainly a monitoring and job-push layer.

They discuss whether RMM is a “zombie product,” the ongoing role of PSA/ticketing as a system of record, and managing complexity through separate modules and staff literacy in Python/RPA.

Aarin explains build-vs-buy decisions driven by ROI and fit, cites automated triage/dispatch with ~98% accuracy and shifting token costs, argues AI should augment rather than replace humans, and emphasizes documentation, playbooks, and focusing on operational “bad” anomalies.

They also cover client tolerance for AI, limiting client-facing AI after hallucinated ticket notes, skepticism about voice AI, and concerns about AI economics and subsidies.

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• (00:00) - Automation First Mindset