All-in-one is definitely the way to go at your size. Managing separate tools creates more sync and troubleshooting overhead than it's worth.
For straightforward management, JumpCloud is a strong contender for your help desk team, but test its policy builder with your real business rules. If your role changes depend on multiple attributes (like department AND location), build that exact logic in a trial to see if it feels intuitive. That's where a "simple" UI can hit a wall.
The biggest migration pitfall isn't the SSO switch, it's the silent overrides in your current Glide provisioning. You'll want to test the entire user lifecycle in your new platform - creation, a role update, and deactivation - on a non-critical app. That's where you'll find the hidden mappings Glide was handling that could orphan accounts or break access.
Automate everything.
Yeah, that dev tools trick is clutch. I used it last year to catch a weird OIDC `email` claim mismatch between Glide and a new analytics app. The connection test passed, but actual logins failed silently for our marketing team.
The JumpCloud reporting trade-off you mentioned is real. It's fine for day-to-day, but when we had a security audit, the manual export-and-merge for a single user's access history across six apps took an afternoon. That "higher-tier platform" cost starts to look reasonable when you're billing hours to an auditor.
Still looking for the perfect one
That export-and-merge audit reality is a hidden cost most don't factor in. JumpCloud's reporting is fine until you need to prove a timeline to an auditor, then you're paying your team to be data janitors.
The OIDC mismatch is another classic case of the connection test being a lie. The real test is a user from the affected team trying to log into the specific app on a Tuesday. Anything less is just a vendor checkmark.
Your CRM is lying to you.
You're right about digging into provisioning audit logs, but that only finds the rules that actually fire. Glide's real funhouse is the unpublished, dormant rules that everyone forgot to disable. Those won't show up in logs because they haven't triggered in years... until you migrate and the conditions are met for a batch of new test users you never considered.
Rippling's integration is its main appeal, but that's also its biggest risk. Tying IAM directly to the HRIS means every data entry mistake in HR - a typo, a mis-assigned cost center - becomes an immediate provisioning event. You trade sync overhead for a new class of cleanup jobs that require HR to fix their own data, which is its own political nightmare.
Trust but verify
You're asking the right questions, but you're starting from a vendor's feature list. That's the wrong end.
The "straightforward to manage" dream is what gets you into another Glide situation in three years. A clean UI doesn't mean simple policy logic. The real complexity is in your undocumented exception cases - the one-off business rule from 2020 that someone in finance needs. Glide is silently running it right now.
So the pitfall isn't disruption during the move. It's finding out, six months after a "successful" migration, that your new platform can't enforce the rule your auditors assume is in place because it was in Glide. You find that by testing your ugliest, most irregular user lifecycles in the trial, not the happy-path demo scenario.
Skip the feature matrix. Build test cases for your weirdest provisioning scenarios first. If the new platform chokes on those, its UI is irrelevant.
Trust but verify
For your size, I'd stick with an all-in-one. Managing separate IAM and PAM tools creates more sync headaches than it solves, especially for a 300-person team without a huge security bench.
On the "straightforward to manage" front, I've found JumpCloud pretty intuitive for help desk folks. The big catch, though, is auditing. As others hinted, pulling a clean access timeline for one user across multiple apps is clunky. You're exporting CSV files and merging them, not clicking one report. For 300 users and basic audit needs, it's probably fine, but just know that's the trade-off for the simpler UI.
The biggest pitfall in moving from Glide isn't SSO, it's those silent provisioning overrides. Map every SCIM attribute and OIDC claim for your core apps *before* you cut over, using a test user. What Glide was quietly fixing for years will break in a new platform that follows the spec to the letter
Dashboards or it didn't happen.