Survive September: the IT lessons schools cannot afford to miss
September hits hard for edtech and IT teams, and this conversation gets straight to the point: how to survive the chaos, keep projects moving, and stop the same avoidable problems from happening again. Matt and Jack unpack the realities of back-to-school season, where summer delivery turns into September firefighting fast.Matt and Jack get honest about the pressure points that hit hardest in education IT— incomplete handovers, missing passwords, fragile legacy systems, and the endless challenge of taking over new schools or new environments with limited context. Jack brings the perspective of moving from a cloud-first world into a hybrid one, while Matt shares what it really takes to support multiple schools, multiple teams, and multiple moving parts without losing control.
You’ll discover:
- Why password management is not optional, especially when people leave or go off sick
- How to separate project support from business-as-usual support so issues do not get lost in the handover
- Why a technical plan, delivery plan, and proper closeout documentation matter more at scale than ever
- How SOPs, screen recordings, and central documentation turn tribal knowledge into something a whole team can use
- Why AI, APIs, and automated data mapping are becoming essential for understanding systems, identity flows, and licensing across schools
Matt also shares how his team is building a live portal that brings together data from systems like Intune, Google, Halo, HubSpot, Bob HR, and more, giving customers and internal teams visibility over devices, licences, onboarding, and procurement. Jack adds a smart angle on identity mapping, single sign-on, and using Claude to help build a clearer picture of where schools are now and where they need to get to.The bigger message is simple: if you do not know what you have, where it lives, and how it talks to everything else, you cannot make good decisions, save money, or move safely to cloud. And if you are in the middle of that September scramble, this episode offers something better than theory—it gives you perspective, practical frameworks, and a reminder that you are not the only one in the middle of it.Perfect for IT leaders, edtech teams, MSPs, and school tech staff who need a realistic reset on documentation, handover, automation, and strategy. If September feels like chaos, this one will make you feel a lot less alone.