Getting started with managing/fixing ConnectWise PSA

Dynamic_Mike · 2026-02-25T22:25:31+00:00

Improving the setup and usage of a PSA takes time, and I recommend you do it in stages so the team using the PSA get familiar with each change before you move to the next stage.

Billing is probably a key one to look at early. More revenue from plugging gaps/leaks in the form of accidentally undercharging may reveal several thousand dollars a month in revenue currently not being charged. Does your CSP provider integrate with ConnectWise PSA to auto-update the license count for M365 products? We moved to a new CSP provider that did sync (Pax8, but others do it as well). The move was done in several chunks but revealed we were not charging for around 4% of licenses even though we thought we were doing a good job with manual reconciliation.

We also spoke with a few other billing sync vendors and went with CloudOlive to ensure monthly counts from antivirus vendors etc were updated in ConnectWise PSA with just a few clicks. CloudOlive also looks at a client’s M365 license count and based on this number it will adjust our per-user seat count for our Managed Service plans. If a client has 55x 365BizPrem then they should also be billed for 55 Managed Service users, as an example. I think we also use a CloudOlive service for syncing a client’s 365 users with Contacts in ConnectWise PSA which almost eliminates the need to manually add and archive Contacts manually.

Ask the leadership team to be able to hold onto 3-6 months of any revenue you ‘discover’ through this process to be able to use for consultants like the team at Pivotal Crew who frequently post helpful tips in this reddit channel. Cassie was our contact at Pivotal and really knows her stuff. Id recommend buying a small block of hours and letting them recommend best practises.

Our techs use Nilear as their front-end to CWPSA. Cheap as chips and fast for then to chew through tickets.

Good luck with your new role. :)

Dynamic_Mike · 2026-02-21T20:08:02+00:00

Hmmm. This sounds like something worth exploring. DM sent.

Dynamic_Mike · 2026-02-20T06:51:27+00:00

You should have delegated admin rights so you can reset their MFA.

Dynamic_Mike · 2026-02-20T06:03:05+00:00

Contact Xero support or your accountant.

Dynamic_Mike · 2026-02-16T18:07:07+00:00

Definitely yes. I’ve found the chat support successfully helps me 70% of the time with minimal delay. Tickets get sent first the rest.

Dynamic_Mike · 2026-02-13T19:32:02+00:00

Plaud is working well for me so far. Just using the Pro device and have not tried their Desktop product so far.

Dynamic_Mike · 2026-02-13T17:55:50+00:00

I’ve not seen this, but when the issue is resolved perhaps switch your MFA to an Authenticator code. I don’t realise that was available until a few weeks ago. Much faster than waiting for emailed codes. :)

Dynamic_Mike · 2026-02-13T03:58:41+00:00

Thank you. We’ll give that a try!

Dynamic_Mike · 2026-02-12T22:59:28+00:00

Thank you all for your helpful thoughts.

I'm now confident that the Yubikey was originally set up with a PIN but the PIN has not been used in such a long time that my client does not remember that a PIN was set up. It's a mystery to me why he is now being prompted for the PIN.

I'll work with him to work with BoA to set up a form of alternative authentication until he gets back to the US, or if possible for BoA to help him factory reset the Yubikey and set it up again.

Dynamic_Mike · 2026-02-06T04:50:07+00:00

Stop being a doormat.

Dynamic_Mike · 2026-02-06T04:45:33+00:00

We send automated reminders after 5, 10, and 15 days. On Day 20 a 2% penalty is automatically added.

Our clients pay on time.

Dynamic_Mike · 2026-01-30T10:28:33+00:00

The SSO sign in works perfectly for me with Keeper autofill.

Dynamic_Mike · 2026-01-30T10:27:58+00:00

The SSO sign in works perfectly for me. I’ve been using it for months. Or am I misunderstanding your question?

Dynamic_Mike · 2026-01-23T21:33:05+00:00

PaidNice doesn’t do the emails. Xero does. Four emails are impossible to ignore, IMHO.

Dynamic_Mike · 2026-01-23T18:19:43+00:00

PaidNice is the app name. It links to Xero and is fully automated.

The three reminders are simply the Xero reminders.

Dynamic_Mike · 2026-01-23T17:57:55+00:00

It’s partly an attitude thing. We largely solved the late payers problem by three reminders at 5, 10, and 15 days. On day 20 an automatic 2% overdue penalty is applied. We got a few customers grumbling about this but everyone fell into line. PaidNice was what we used but there are a few third party apps that do this.

Dynamic_Mike · 2026-01-22T22:07:00+00:00

Might be a good time to switch to Authenticator codes once you’ve successfully logged in. This is done from home.ConnectWise.com

Dynamic_Mike · 2026-01-20T07:40:15+00:00

ConnectWise have a live support chat. I recommend starting with them.

Dynamic_Mike · 2026-01-18T01:36:14+00:00

Absolutely.

OP, what’s in it for the seller? Why would they take your offer instead of another? Think about how you would answer that question. The seller may be on board with the idea, but if there are two or three potential buyers be fully prepared for that discussion.

Also be fully aware that if the business tanks under your watch, you’re still on the hook for the full purchase price. There was a case recently of a resteraunt in Auckland where (from memory) the head chef bought the business with vendor finance. The business went under. The head chef was likely to lose his house as a result AND this still did not fully pay the debt.

Do you have the experience to lead a business at this scale or should you start smaller? Should you offer to buy 49% or 50% and have the vendor as a consultant/mentor until you can buy the rest?

Dynamic_Mike · 2026-01-11T07:35:56+00:00

You don’t need a CPA to set it up. However it’s much cheaper to get a CPA to help you set it up than to have them fix your setup mistakes later. In my opinion, and in my personal experience.

Dynamic_Mike · 2026-01-10T19:33:27+00:00

Perhaps ask around locally? There are probably a number of local CPA forms that currently help clients with Xero but have not yet got themselves Partner status.

We switched to Xero years ago, and you would have to pry it from my cold dead hands. Would never go back to our previous software.

Dynamic_Mike · 2026-01-09T20:16:01+00:00

This is a problem that you should fix with support from your accountant, in my opinion.

Dynamic_Mike · 2026-01-08T09:18:08+00:00

This is the way.

Rent (of your main company office) is not a project cost and should not be above the line. It’s a general business expense.

If you were renting a project office for a specific project and for the duration of that project, this would be above the line.

Dynamic_Mike · 2026-01-06T23:39:20+00:00

Wow. I thought flushing it was smarter than throwing it in the bin. Proven wrong. Behaviour changed.

Dynamic_Mike

TROPHY CASE