By John Stroili, VP of Sales with over 25 years of experience driving IT strategy and growth across industries
Choosing a managed IT services provider (MSP) isn’t just a tech decision – it’s a growth decision.
Today’s businesses aren’t just looking for outsourced IT support. They’re looking for strategic alignment, deep security expertise, and a partner who understands the regulatory and operational complexity of their industry.
As conversations with decision-makers across sectors show, the MSP landscape is crowded – and the stakes are high. Cost and coverage matter, but they’re just the beginning. What truly separates the right partner from the rest is how they position your business for what’s next.
Here’s how to evaluate MSPs in 2025 – and what to prioritize if you’re serious about long-term value.
An MSP should do more than keep systems running. It should bring together the tools, expertise, and strategy to elevate your IT function – not just maintain it.
Look for a provider that covers the full spectrum: cloud, cybersecurity, help desk, BDR (backup and disaster recovery), compliance guidance, and strategic input through vCIOs or vCISOs. If those services aren’t integrated, or feel like an afterthought, your growth will hit a ceiling fast.
That’s especially true when it comes to cybersecurity. As Omega Systems CEO Mike Fuhrman has emphasized: “Security shouldn’t be a bolt-on.” It should be embedded into every layer of the relationship – from onboarding to architecture, policy, and day-to-day monitoring.
True MSPs don’t just respond to tickets – they anticipate needs, identify risks, and offer insights that shape your roadmap.
This means leveraging modern monitoring tools, sharing regular health checks and performance trends, and meeting with your leadership team to align IT with business outcomes. If your current provider only shows up when something breaks, you’re not getting proactive value – you’re getting a help desk.
The needs of a healthcare provider, a law firm, and a financial institution aren’t interchangeable – and your MSP should know that. It’s not just about understanding compliance frameworks like HIPAA or SOC 2. It’s about understanding the operational pressures, the workflows, and the stakes.
Look for MSPs with real-world experience in your space – backed by case studies, references, or certifications that show their credibility in highly regulated industries. As one executive at Omega put it, “An IT provider who understands your industry’s nuances is more likely to be the right fit for your environment.”
Your MSP should grow with you – not slow you down. Whether you’re adding new users, launching a new location, or adopting a new platform, your provider needs to scale seamlessly.
This means more than just adding tools. It requires thoughtful integration – making sure new technology aligns with your existing stack, doesn’t duplicate functionality, and supports your long-term goals. Without that strategic lens, it’s easy to introduce unnecessary complexity or cost.
Regulatory pressure is mounting across industries. Your MSP shouldn’t just be familiar with your requirements – they should help you stay ahead of them. From cloud environments to data governance, compliance should be woven into their delivery model, not tacked on during audits.
Ask how they support frameworks like SOC 2, HIPAA, or CMMC. Just as important, ask how they help you reduce the internal burden of compliance – through automation, reporting, and process design.
Support transparency is non-negotiable. Service level agreements (SLAs) should clearly define what success looks like – from guaranteed response times to uptime benchmarks and escalation processes.
But good SLAs aren’t just about what’s written – they’re about what’s delivered. The best MSPs back up their promises with real-time visibility, regular performance reporting, and a culture of accountability.
Review SLAs critically. Then ask how your provider tracks performance and ensures follow-through. If they can’t show you the metrics, it’s just a promise.
The best MSPs don’t just resolve issues. They build relationships. That means having a named account manager, regular check-ins, and strategic business reviews – not just a rotating support rep or portal login.
Real partnership shows up in the moments between the problems – in how often they reach out, how well they understand your business, and how quickly they adapt when your needs change.
If your MSP can’t articulate how they stay aligned with your goals, they’re not acting like a partner. They’re acting like a vendor.
In today’s market, IT can’t just support your business – it has to help grow it. The right MSP offers more than relief from day-to-day IT burdens. It brings long-term alignment, built-in security and compliance, and scalable infrastructure that’s ready for change. Most importantly, it brings a true partnership – not just a contract.
“What excites me most about Omega isn’t just where we are – it’s where we’re going. We’ve built a business grounded in trust, accountability, and deep technical expertise, and we’re evolving every day to meet the changing needs of our customers.” —Mike Fuhrman, CEO, Omega Systems
Whether you’re reassessing your current provider or evaluating your first MSP, the next step isn’t a sales pitch – it’s a conversation. Let’s take a clear, honest look at where your IT stands, where it could go, and what it would take to get there. No pressure – just perspective.
ABOUT THE AUTHORJohn Stroili brings over 25 years of IT and operations expertise, helping organizations implement tailored solutions to drive growth and efficiency. As VP of Sales at Omega Systems, he focuses on aligning innovative technology with business goals to address the complex challenges businesses face today. Read John Stroili’s full executive profile here.
Connect with John on LinkedIn.