QuestingHound’s journey from a traditional IT business into a tightly run MSP showcases operational discipline, consistent reporting, and vendor partnerships can transform a service organization. After years of tool sprawl and inconsistent execution, Partner and Chief Service Officer Ray Medina rebuilt QuestingHound’s service engine around documented processes and accountability. QuestingHound made a pivotal move—implementing ConnectWise NOC Services (NOC) for x360Recover andelimieliminatre than 25 hours per week of manual backup success, reduced daytime escalations to near zero, and gave engineers the headroom to invest in playbooks, documentation, and proactive client experience. As Medina puts it, “That has been the biggest win for us. We can sleep. We don’t have to worry about it.”

From VAR roots to MSP discipline

Founded in 2001, QuestingHound started as a traditional IT provider (VAR) and gradually shifted to managed services as the market changed. “People stopped buying hardware,” Medina recalled, pushing QuestingHound toward recurring services around 2014 and fully into the MSP model by 2017. The company anchored its operations with ConnectWise PSA from the moment it formalized the MSP pivot. In Medina’s words, “We started with ConnectWise PSA, marking the moment we took steps to formally become an MSP.”

By the time Medina arrived in 2022 as Service Delivery Manager— and after becoming a partner, and then Chief Service Officer. QuestingHound accumulated roughly 20 different tools across its stack. The effect was predictable: data and process fragmentation, inconsistent behavior, and extra work stitching together signals from disparate systems. As Medina summarized candidly, “We had approximately 20 different tools that we were using.” Tool sprawl wasn’t the only problem -years of well-intentioned, but ad hoc choices had weakened the company’s operational muscle.

The Reality Medina Walked Into: Chaos, Then Rebuild

When Medina stepped in, the service department showed deep cultural and process drift. Engineers cherry-picked tickets according to personal preference without dispatch, and time tracking was unreliable. The company possessed thorough, “C-level  style documentation and playbooks, but execution lagged far behind intent. “Although the organization had well-developed playbooks, they weren’t being applied consistently across the team,” Medina said. Beyond that, the team had made a common MSP mistake: promoting the best engineer into a service manager role without managerial training. It didn’t stick. The service department was suffering.

Medina is the first to describe himself as process-first: “I’m a process guy. I like things nice and neat, predictable.” He also wanted to preserve QuestingHound’s calm culture, and he said in jest, “we’re not delivering babies or chasing ambulances, you know, we’re growing flowers”, without letting “relaxed” become a license for chaos. His mission for the first 18 months was straightforward and relentless: align execution with the playbook, instrument dispatch, enforce accountability, and rebuild trust internally and with customers.

It was not painless. As Medina puts it, “A few team members recognized that the direction we were moving, toward stronger process consistency, didn’t align with how they wanted to work. I’m as laidback as they come, but following our processes is essential to delivering a great experience  for our customers.” 

Six engineers departed during that period; the team that remained stabilized and has now operated together for three years, with predictability replacing improvisation. The before picture was stark: “Our numbers were totally upside down, all in red, and it was chaos, but it was a great challenge.”

The after picture: a service organization that knows what it’s doing and why.

The Turning Point: Handing Backups to the ConnectWise NOC Services

QuestingHound had used Axcient x360Recover for approximately four years, even prior to Axcient’s move under the ConnectWise umbrella, and historically performed its own backup monitoring and remediation. Meanwhile, the company had long leveraged ConnectWise NOC Services for workstations and servers. 

Backups, however, were a different story: the team rotated the task of daily checks among engineers, and the variability showed. “We used to rotate it where every day a different engineer does a backup check,” Medina explained. “Some engineers will do it faster, some engineers will do it slower, some engineers will forget to do the actual check.” The inconsistency wasn’t just about speed or thoroughness; it eroded accountability. And the opportunity cost was severe: “We were spending at least 25 hours a week doing backup checks,” even on a slow week. Medina and the managing partner penciled out the number of hours spent cross-checking their positive backup reports to compare the cost of internal time against NOC pricing. The answer was immediate: “It’s just a no-brainer. Let’s do it.”

About six months ago, QuestingHound activated Co-Managed Backup with ConnectWise NOC Services for x360Recover protected systems. The team expected incremental relief. What they experienced instead was a structural shift: consistent, checklist-driven oversight performed the same way, every day, 24/7—an operational heartbeat impossible to replicate with a rotating human schedule.

Implementation: From Variability To a Trusted Process 

The hallmark of the NOC engagement was consistency. Medina described the effect on accountability this way: “We know it’s done; we know it’s checked the same way every single day.” If a backup hiccupped at 3:00 am, the organization no longer arrived at 7:00 a.m., leaving the team surprised and scrambled. The NOC had already remediated or escalated any failed backups as needed. “It’s a 24-hour thing that you don’t have to worry about,” Medina said. “You know the backup didn’t run at 3:00 in the morning—you come in at 7 and you must rerun it. It’s already done.”

Time Back, Clarity Up, Stress Down: 25+ Hours Per Week Reclaimed

QuestingHound benefited from capacity gains after its engineers no longer needed manual checks to make sure all backups were performed as scheduled, and it also eliminated the productivity drag of daily rotations and context switching. High-value engineers weren’t spending peak energy on low-leverage tasks. With that reclaimed time, the team leaned into work that compounds value: “It has given us more time to create new playbooks, create documentation, support,” Medina said. Those improvements drive consistency across service delivery and accelerate onboarding of new staff, which in turn improves margins and customer satisfaction.

Because backups are now verifying the same way daily, accountability is no longer an issue. Exceptions are surfaced and get resolved. During the first six months of NOC co-managed backups, QuestingHound saw only one or two escalations. “They escalate when they need to, maybe one, maybe twice in six months.” That’s the point: when consistency rises, noise falls.