Thank You ConnectWise For Showing What Great PSA Automation Looks Like

I was so pleased when Stephen put out the call for a guest writer for this week. I am a huge proponent of the MSP Community that has given so much to me, and I look forward to any opportunity I can take to give back.  

Instead of the usual Advanced Global article on how to improve Autotask, I’d like to pause and talk a bit about the WHY - why a properly configured PSA is important and what it’s done for me. And to thank ConnectWise (yes, I am not kidding) for showing me the way. I’m not sure I’d be where I am today without them. 

The Path to Success in the MSP Space 

I’d like to think I’ve been pretty successful in the MSP space. I’ve built and sold an MSP and worked successfully in the space. But it wasn’t always that way. Like many people in the MSP world, I was in Corporate IT back in ’99 and found the IT services industry after my Fortune 500ish healthcare company outsourced.  

Like many, I became a struggling freelancer - doing great work - but not making a lot of money. And like many MSP owners today, contracting morphed into running my own break/fix business that still wasn’t making much money. In fact, I estimated I would be laying off my Team and closing the doors within 90 days when I met the people from ConnectWise that changed my life. (and ASCII – my family owes much of our wonderful life to that organization). 

If you’ve ever seen an episode of “The Golden Girls,” then you understand this lead-in used by Estelle Getty’s character when she tells a story: “Picture it. Chicago. 2009. A scared break/fix owner about to go bankrupt gets an email late in the evening about an event 4 hours away that would have tools to help. After some discussion, the owner’s young wife says to take the last $200 in the checking out and go with a tearful goodbye and prayers that something at this ASCII Success Summit will save their lives. 

Could a Vendor Called ConnectWise be a Game-changer?  

I won’t bore you with the details. But, I had a client server-down emergency on the way there, and I spent more time remoting in and fixing things than paying attention to the speakers. But I did manage to watch a presentation from a vendor called ConnectWise about something called a Professional Services Automation Tool that could do all sorts of cool things.  

And it had checklists! I knew what a ticketing system was from my corporate days, but I had no idea there was anything for little break/fix shops other than email and Excel. The idea of being able to put in tickets and add checklists to them and then bill those hours seemed like the answer to my prayers! I knew we were working hours and not billing for them and not working things we were asked to do, so this seemed great.  

Oh, and they talked about this thing called “Managed Services.” I was just trying to eat…and trading time for money was easier accounting. So, I decided I’d look into this MSP thing someday when I had time...maybe it could be made to work? 

And then there was Autotask… 

So I decided to buy ConnectWise. It turns out that they needed 90 days to get my database set up. But there was just one small problem with that…I was going to be bankrupt by then. Out of desperation, I called another company at that event called Autotask. They didn’t have checklists (and didn’t for 10 years), but they could have me up in 48 hours.  

48 hours later, we went live in what I can only call a “crash implementation.” I would never recommend anyone doing this.  We solely focused on ticketing and ignored everything else. And I learned about the system the hard way.  

There was no Advanced Global to call, so I got what I could out of my five implementation calls. And Autotask did a great job structuring onboarding to my needs. It was hard, but we did it. And we immediately saw the capture of lost revenue.  

Not only were we actually billing for work done, but we were actually doing (and BILLING!) work that had been missed with email only. Not only did we stop the bleeding, but we were actually making money!!! 

So yes, because ConnectWise did a great presentation to a newbie on Managed Services and PSA, but couldn’t deliver, I started my glorious career using Autotask PSA (and later, Datto RMM). I originally built Autotask exactly like the documentation said – AT support was always amazed at how the setup was by the book, as most SMB IT Providers didn’t put in the time.  

Of course, I had built it for the 100-person IT company I wasn’t, so there were lots of options when adding a ticket that made it more difficult for Techs. Over several years, I worked to rebuild AT several times until the setup finally made sense for an MSP of under 15.  

Now Back to That MSP Thing 

Oh, and that MSP thing worked out pretty well for us when I finally implemented it. So much that I accepted an unsolicited offer in 2018 and sold my business. I then went to work for a ConnectWise shop. Tools are tools, after all, and I didn’t think it would be as much of a shock as it actually was.  

What I learned is that tools may be tools, but the time and effort, and knowledge that is put into configuring them makes a HUGE difference in how your MSP runs. 

No matter what the tool, if it’s not optimized for your MSP and best practices haven’t been implemented, you won’t be as profitable or have as good of a Service Delivery experience for Clients as you could have.  

Especially with a tool like ConnectWise that requires months (years?) of training to use and costs so much in time and money. Now I’m not picking on ConnectWise, as many out there are extremely successful using it - I’m just pointing out that my two years of using ConnectWise taught me the value of proper configuration and management buy-in for a PSA tool. 

Needless to say, I was very happy to move back to an Autotask shop.  

But this was a different Autotask. 

I had been using the product for years. I was part of the panel that advised on the new UI around 2016. And I was very good at optimization. Or so I thought…until I saw an Autotask that had been aligned and purposefully set up to manage the Service Delivery experience from ticket creation to billing.  

An Autotask that had dashboards customized not only for a best-in-class MSP but for the various roles in that MSP. Autotask dashboards with widgets crafted based on years of experience from Autotask experts. An Autotask that had reactive and non-reactive tickets categorized in ways that allowed the widgets to show the Technicians what tickets to work next. And an Autotask that you could pull reports that made sense and allowed actionable change. Wow!  

I spent eight years in Autotask, learning and tweaking and coming up with what I thought was a setup that worked for my small MSP. And I spent two years trying to learn ConnectWise and getting management and Team buy-in for data-driven change.  

And then I experienced what an Autotask PSA looks like when configured by people who truly live and breathe Autotask. 8 years or a couple of weeks...I think I know what I would choose if I ever had to do it again.  

Of course, the learning never stops.  

An MSP cannot just buy a tool, configure it, and leave it alone.  

A Service Coordinator who can take ownership of the PSA, track the tickets, manage the day-to-day details of the Techs, and maintain ongoing training on Autotask is an absolute must. You can outsource this role and the Autotask upkeep successfully, but my MSP chooses to have me handle those tasks.  

To stay successful, I am a member of the Service Delivery Gladiator Community, which has helped me immensely with a place to share and post with other Service Coordinators as well as provide a great resource library on how things should be done.  

A phenomenal free resource is the “Ask the Experts” Webex calls on Thursday nights and Friday mornings. I try never to miss a Friday call, as this is a peer group of my peers (and Carol – an awesome Autotask expert) who can always set me straight on an idea or tell me how to do something in Autotask.  

I have grown so much in learning Autotask Workflow Rules and automation and have most Autotask actions automated (that’s a story for another article). Now, if I needed a LiveReport written…I’m too busy for that, so I just write a check, and it’s done in a couple of days.  

I used to think Autotask was awesome with the years of effort I put into it. Now I know what an awesome, data-driven, Client goals aligned Autotask really looks like. And I have ConnectWise to thank for it. 

Guest Writer, Matt Adkins SunPoint IT