ConnectWise’s Jamie Hunter is betting that the next few years will determine which MSPs and office technology resellers make the leap from reactive IT to predictive, intelligent operations. As chief strategy, operations and marketing officer, she sits at the intersection of ConnectWise’s platform roadmap, partner experience and go‑to‑market execution, and she is explicit about where she thinks the industry is headed and how fast it is moving. Hunter is a powerhouse, and after speaking with her, I have no doubt she is right on target.
Join me and Jamie Hunter in the SpeakEasy as we discuss ConnectWise’s strategy around AI, automation, security and community.
A fast curve jump, not a gentle slope
When Hunter joined ConnectWise in September 2025, the company was already well into its journey to unify a fragmented stack of tools and services under a single platform architecture. Her initial remit covered strategy and operations; in January she added marketing, creating a role that connects long‑term direction, day‑to‑day execution and the way the company tells its story.
She describes the current moment as one in a series of “curve jumps” that have reshaped the IT services landscape over time. This one, she believes, is different. “This new one, I actually think will be the fastest moving curve jump of them all,” she says, driven by automation and AI but rooted in a deeper shift in how MSPs and dealers run their businesses.
For Hunter, the headline is not AI adoption; it is the evolution from reactive, human‑driven operations to predictive, system‑driven intelligence. Many providers still depend on humans to chase tickets, monitor alerts and stitch together context from siloed tools. In the world ConnectWise and the executive leadership team are steering toward, intelligent systems will handle much more of that detection, correlation and recommendation work, leaving people to focus on what to do with the insights.
She is clear that AI by itself is not the landing point. “AI is not the destination,” Hunter says. “Predictive intelligence is the destination.” Automation, in her framing, eliminates repetitive tasks and speeds up execution, but the real value comes from systems that are always learning, spotting patterns earlier, surfacing risks sooner and, over time, making bounded decisions on their own.
That distinction matters to MSPs and office technology resellers because it sets a higher bar than “add a bot, call it done.” Moving toward predictive intelligence requires both new tooling and new discipline in how businesses are structured and run.
“You can’t automate through chaos”
To explain that discipline, Hunter returns to a line she heard from Brian Luckey of Integris: “you can’t automate through chaos.” For someone responsible for strategy and operations, it is both a warning and a filter. No amount of AI or RPA will rescue a brittle process built on inconsistent data, ad‑hoc workarounds and tribal knowledge.
In practice, that means she spends as much time talking about foundations as she does about innovations. She argues that partners must first stabilize and standardize their environments. This is what she calls “getting the house foundation in place” before they can meaningfully benefit from AI’s speed. Broken workflows do not become better because they are automated; they just become wrong faster.
Internally, Hunter says ConnectWise has moved “from AI aware, to AI focused to AI first,” and that progression has forced hard choices about where to embed intelligence and how to avoid layering complexity onto complexity. It shows up in the emphasis on a unified platform, a shared data layer and common services that can be reused across products and workflows.
Externally, she believes the providers who will pull ahead in this curve jump share a few traits. First, they think in at least three‑year horizons rather than chasing only the next quarter, and they lean into change instead of clinging to “we’ve always done it this way.” Second, they embrace standardization of tools, processes and offerings, so that optimization and automation have something stable to work with. Third, they build operational discipline into their calendars, carving out real time to pull apart how their businesses run and to redesign them with intelligence and automation in mind.
Hunter pushes leaders to regularly block hours of time for this kind of work. She argues that only by mapping and questioning each step – from quoting and onboarding to ticket triage and project delivery – can providers identify the points where AI and automation will materially change the economics of their operations.
Integration, acquisitions and the value of connection
Hunter’s bias toward integration did not start at ConnectWise. She arrived with a portfolio of mergers and transformations behind her, and those experiences shaped how she thinks about value creation. She calls herself “a natural, curious person” who asks a lot of “why” and “how” questions; when confronted with something new, she is just as likely to sit down and teach herself as she is to call in outside help.
The core lesson she took from those deals is that “the value of connection outweighs the value of individual parts.” In her view, an acquisition only creates value when integration is disciplined, intentional and completed with urgency. Too many buyers, she says, assume the benefit lies in buying the company, when the real benefit lies in integrating it in ways that produce “1 plus 1 equaling 3.”
That same thinking underpins the company’s platform strategy. The move to a unified platform is not, in her telling, a branding exercise; it is a practical response to years of accreted products and features. When you accumulate tools without integrating them, you accumulate complexity for partners. When you connect those capabilities around a shared data layer and unified positioning, you create the conditions for the predictive intelligence she is aiming for.
ConnectWise is the ecosystem player
If integration is Hunter’s structural theme, community is her cultural one. ConnectWise has long positioned its partner ecosystem as a differentiator and drives that as part of their operating model. She points to IT Nation Connect as a visible expression of that ecosystem, and shows that the community itself has a say in how things evolve.
More important, though, are the recurring touchpoints: Evolve peer groups, user groups, advisory councils and regional sessions. Her emphasis in those rooms is on listening first. “It’s not about telling and leading, it’s about listening and leading,” she says.
The same community ethos shapes how ConnectWise builds and prioritizes its roadmap. Hunter talks about advisory structures and university programs that keep the company close to partner needs and stresses that roadmaps are not drawn up in a vacuum. Instead, she positions them as joint planning exercises: “Where do you want to be in three years, and where does that mean we need to be in three years?”
Security, speed and “minutes that matter”
No discussion of AI and automation in today’s MSP landscape is complete without addressing security. In her view, cybersecurity “cannot be a disconnected layer.” It must be part of the same integrated system that connects operations, automation and analytics.
She highlights two realities that are particularly relevant for resellers. First, MSPs are prime targets because they sit in the middle of so many customer environments. Second, threats are becoming more automated and more identity‑driven, which means defenders cannot rely on manual processes or loosely coupled tools.
Hunter’s answer is to emphasize both integration and speed. On the integration side, she points to work connecting security operations more tightly with the broader ConnectWise platform so that detection, response and remediation are informed by the same data and context as service operations. On the speed side, she highlights what she describes as the industry’s first 15‑minute SLA for managed detection and response – a move from aspirational SLOs to contractual commitments that recognize how much “minutes matter” when an incident unfolds.
The message to MSPs and dealers is straightforward: if your security stack and processes are not both integrated and fast, you are giving attackers an unnecessary edge. For Hunter, this is part of the broader predictive intelligence story. The same models and automations that make service operations more efficient can also compress detection and response windows, but only if the underlying systems are connected and the processes are clear.
A Predictive Future, Built Together
Taken together, Hunter’s themes of predictive intelligence, disciplined integration, community‑driven strategy and security as a first‑class concern paint a clear picture of where ConnectWise thinks the market is heading and what it expects of its partners.
For resellers, the message is both encouraging and challenging. Hunter’s emphasis on connection and community aligns with the relationship‑driven culture already well established in the channel, but the shift she describes will require a level of operational discipline, standardization and comfort with AI‑assisted decision‑making that goes beyond traditional hardware and break‑fix services.
Hunter does not downplay the pace. She believes what once took years will soon take months, and processes that previously consumed weeks of human effort can now be compressed into minutes with the right combination of AI and automation. She also rejects the old “first mover penalty” narrative, arguing that those who lean into curve jumps “get there first” and “get there stronger,” especially when they are willing to “fail fast” and adjust rather than waiting for perfect answers that may never appear.
The technology is important, but what really gives her confidence are the people around her. Hunter describes the ConnectWise ecosystem as truly focused on being better together and sees her role, along with CEO Manny Rivelo and the rest of the leadership team, as carving out paths that partners can walk with them. In a landscape where it is easy to feel like you are running just to stay in place, that kind of shared journey may be more important than any single feature in the new platform.
Patricia Ames is president and senior analyst for BPO Media, which publishes The Imaging Channel and Workflow magazines. As a market analyst and industry consultant, Ames has worked for prominent consulting firms including KPMG and has more than 15 years experience in the imaging industry covering technology and business sectors. Ames has lived and worked in the United States, Southeast Asia and Europe and enjoys being a part of a global industry and community.