Claude’s desktop app needs admin rights to turn on Cowork, the mode that lets Claude work on files on the computer. Without admin, the app installs and Cowork is missing.

Public bug reports say that moving users’ folders off the main drive, a common IT setting, can stall setup. The workaround is one local folder for Claude work.

Connecting AI to Microsoft 365 should start with the least access that works: specific mailboxes and SharePoint sites, a dedicated service account, and approvals in writing.

Once Claude connects to a Google Workspace Gmail account, the admin console flags it as a “risky app.” Warn your admin first so nobody reads it as a security incident.

What is an agency management system?

The system of record for an insurance agency: clients, policies, carriers, and renewals. Applied Epic, AMS360, and AgencyBloc are examples.

Should I replace my agency management system?

Usually not first. Map how work moves, then fix the handoffs around the system of record.

Should an agency build or buy software?

Buy the core system and anything that handles extremely sensitive health information. Build the connections between systems.

What should I ask in a software demo?

Whether your data can get out, in what format, and who will own the login.

Does DoBetter only build custom tools?

No. Chris Cordon builds most things, and he’ll pick, set up, and put guardrails on an existing product when that’s the right answer.

Why does Google Workspace flag Claude as a risky app?

The admin console flags it once Claude connects to Gmail, so warn your admin during setup.

“I’m the wrong guy to ask that question to because I build everything.” How to pick insurance agency software anyway.

Why is picking insurance agency software so hard?

Picking insurance agency software is hard because every vendor demos the easy version. Your agency has a census in a spreadsheet, a carrier portal with no export button, and an account manager who keeps her own tracker because the system doesn’t show what she needs.

The software you already pay for also overlaps. An agency can easily run an agency management system, a CRM, an email tool, a quoting tool, and a shared drive at once, with nobody sure which one holds the real answer.

What do most agencies try first?

Most agencies try replacing the whole system. Sometimes that’s the right call. Often the old system was fine, and the real problem was the typing between it and everything else.

The other move is adding one more tool for each new pain. Together they create more places to type the same thing.

Wanna fix it?

Software that doesn’t fit your agency gets fixed with software selection that starts from a map of how your work moves, a build or buy call made one task at a time, and setup done with the least access that works. Here’s the order I use.

Keep the agency management system as the system of record. Applied Epic, AMS360, AgencyBloc, whatever you run: it holds the clients, policies, and renewals. New tools read from it and write back to it.
Buy anything that touches extremely sensitive health information. If it has to do with extremely sensitive health information, I’m not going to touch it. Use the product built for that job, or leave that system alone.
Ask one question in every demo: can the data get out? A tool that traps your data is a tool you’ll retype from forever.
Write down who owns each login and what it costs each month. My discovery whiteboard has a card for every tool with both fields, because nobody ever knows.
Build the connections. The census that turns itself into a carrier file and the quote that becomes a proposal live between systems. That’s where the retyping is, and that’s what I build.

What goes wrong when you set up new software?

Setting up new software at an agency is mostly permissions and surprises. Here are a few from setting up Claude on managed Windows PCs for a client engagement.

Admin rights.: Claude’s desktop app needs admin rights to turn on Cowork, the mode that lets Claude work on files on the computer. Without admin, the app installs and Cowork is missing.
Moved folders.: Public bug reports say that moving users’ folders off the main drive, a common IT setting, can stall setup. The workaround is one local folder for Claude work.
Email access.: Connecting AI to Microsoft 365 should start with the least access that works: specific mailboxes and SharePoint sites, a dedicated service account, and approvals in writing.
Scary alerts.: Once Claude connects to a Google Workspace Gmail account, the admin console flags it as a “risky app.” Warn your admin first so nobody reads it as a security incident.

Can you choose agency software yourself?

Yes, you can choose agency software yourself, and for a single tool you should. Write down the three tasks the tool must handle. Ask every vendor to demo those three with your own sample data. Ask where your data goes if you leave. Check your client contracts before connecting any tool that reads client information.

Choosing alone stops working when the new tool has to talk to three others. One tool, pick it yourself. A tool that has to connect to everything, map how work moves first.

Quick answers

What is an agency management system?: The system of record for an insurance agency: clients, policies, carriers, and renewals. Applied Epic, AMS360, and AgencyBloc are examples.
Should I replace my agency management system?: Usually not first. Map how work moves, then fix the handoffs around the system of record.
Should an agency build or buy software?: Buy the core system and anything that handles extremely sensitive health information. Build the connections between systems.
What should I ask in a software demo?: Whether your data can get out, in what format, and who will own the login.
Does DoBetter only build custom tools?: No. Chris Cordon builds most things, and he’ll pick, set up, and put guardrails on an existing product when that’s the right answer.
Why does Google Workspace flag Claude as a risky app?: The admin console flags it once Claude connects to Gmail, so warn your admin during setup.