When Waterdog first implemented ConnectWise PSA, the system was technically working, but it wasn’t working well.
As Fred Robinson, Owner of Waterdog, put it:
“We knew it was set up to be functional, but I knew it was not set up to be efficient, and it was not set up properly.”
Like many MSPs, Waterdog had completed the initial setup and training… but quickly hit the reality that “basic setup” doesn’t automatically translate to real-world operational success.
That’s when Waterdog partnered with Pivotal Crew, and everything changed.
“We Didn’t Know What We Didn’t Know”
Fred describes the early days of PSA adoption in a way that will feel familiar to a lot of MSP owners:
“When we first started with you, we didn’t know what we didn’t know… which is a lot.”
Waterdog had migrated from an older PSA that lacked project management, procurement, and workflow capabilities. When they switched to ConnectWise PSA, their team tried to replicate their old habits inside a new platform, without realizing how much potential they were leaving on the table.
“We were clueless… we were not taking advantage of what ConnectWise PSA had to offer.”
A Methodical, Phased Approach That Made Everything Click
What stood out most to Fred wasn’t just the technical improvements, it was how the improvements were delivered.
“There was a spreadsheet… different phases… it was very methodical. You thought out the process quite well.”
Instead of overwhelming the team with a giant overhaul, we worked step-by-step, helping Waterdog implement changes in a way that supported daily operations (not disrupted them).
Fred emphasized that Pivotal Crew was careful to test, train, and support the team through each rollout:
“You were very careful to not go live with anything until everybody knew about it… and when we went live, you were available… to solve any hiccups.”
Efficiency Isn’t Just Nice, It’s Profitability
Waterdog didn’t just “clean things up.” They became a more mature MSP with better control over billing, quoting, agreements, and operations.
Fred summed it up plainly:
“By making it more efficient, [it] made us more profitable… The ability to bill properly… you instituted early on.”
That included improving how Waterdog handled:
-
Ticket statuses and workflows
-
Work types (onsite, remote, maintenance, warranty, travel, etc.)
-
Agreement setup and billing accuracy
-
Product and classification cleanup
-
Reporting and visibility into what’s happening day-to-day
And in the MSP world, billing accuracy is everything:
“If we don’t bill right, we don’t collect right… We don’t make any money.”
Faster Quoting + Automation That Saves Hours
One of the biggest wins for Waterdog was improving their quoting-to-sales-order-to-agreement flow using ConnectWise CPQ.
Fred described how time-consuming the process used to be:
“I’d open up the sales order… I’d manually enter them in the agreement… probably an hour plus… Now it’s automatic… It saved me a tremendous amount of time.”
That’s the kind of operational improvement that doesn’t just feel good, it frees leadership up to focus on growth instead of admin work.
Ongoing Support That Feels Like an Extension of the Team
Waterdog didn’t just hire a consultant for a one-time project. They gained a long-term partner.
Fred explained the difference between ConnectWise support vs. Pivotal Crew support like this:
-
If it’s a true ConnectWise error/bug, he goes to ConnectWise.
-
If it’s workflow, process, configuration, billing, or “how do we do this better?”, he goes to Pivotal Crew.
And the process is smooth:
“We have a chat with you guys that automatically creates a ticket… you respond… we schedule time… it’s automated… bang, bang, bang, it’s done.”
Often, it doesn’t even require a meeting:
“Many times we don’t need to get online… you say ‘Oh okay, I’ll create the workflow’… we test it… it’s perfect.”
Quarterly Reviews That Catch the “Small Leaks”
Even after Waterdog reached a high level of maturity, the proactive check-ins continued to deliver value.
Fred shared how quarterly audits helped identify issues that were small, but important:
-
Products cluttering selection lists for technicians
-
Product class setup preventing agreements from flowing correctly
-
Agreements showing negative profitability
-
GL/accounting best practice improvements in collaboration with their bookkeeper
“It’s nice to know those things exist so I can plug them up.”
Trust Built Over Years (and That’s the Real Win)
Fred didn’t hold back on what this partnership means to him:
“Having worked with you for so many years, there’s a certain level of trust… I don’t question what you tell us.”
That trust even extends to working directly with Waterdog’s bookkeeper without requiring owner involvement:
“As the owner of Waterdog… I know it’s being handled properly.”
And in his words, the monthly support is worth every penny:
“The money we spend monthly is well worth it.”
“You Find the Needle in the Haystack”
One of the strongest parts of Fred’s testimonial is how he explains the value of expertise, not just knowledge, but speed and confidence.
“I used to spend hours, if not days, trying to research a problem… Now I just reach out to you… Why waste my time?”
Then he delivers the perfect line:
“That’s what I’m paying you for. You find that needle.”
The Bottom Line
Waterdog came to Pivotal Crew knowing their PSA was functional, but feeling like it could be doing more.
Today, they’re operating as a more mature MSP with:
-
Stronger workflows
-
Better billing accuracy
-
More automation
-
Cleaner data
-
Better reporting and decision-making
-
More confidence in their operational foundation
And if Fred had to sum it up simply?
“You guys are good… You’ve got my complete trust.”
Want the Same Results in Your ConnectWise PSA?
If your ConnectWise PSA is “working”… but you know it’s not working efficiently, we can help you get there.
Pivotal Crew helps MSPs clean up, optimize, and scale their PSA operations through practical improvements that stick.
📩 Reach out to learn how ongoing optimization and support can help your team run smoother, and bill smarter.