Managed services have changed fast. Clients still want support that’s quick and reliable, but they’re just as focused on security, cost clarity, and advice they can actually use to make decisions. That’s pushed MSP leadership into a bigger role—part operator, part strategist, part risk manager.
A lot of the people setting the pace right now are women who are building stronger teams, sharpening service delivery, and raising expectations across the industry.
Here are five female leaders redefining managed services today—starting with Cortavo’s CEO—plus one bonus name that deserves the spotlight for the impact she’s making.
Managed services have become more demanding as pressure hits from several angles at once. Security threats are rising, and even smaller organizations are frequent targets. Clients want evidence—clear controls, documented processes, and an MSP that can explain what happens before, during, and after an incident.
Budgets are tighter too. IT investment continues, but leaders expect predictable costs and clear outcomes. That pushes MSPs to standardize environments, tighten service design, and link spend to results like reduced downtime and faster onboarding.
Insurance and compliance are adding more weight. SMBs now face cyber insurance reviews, regulations, and vendor requirements, and MSPs are expected to implement and document baseline controls such as MFA, backups, endpoint protection, patching, and access governance.
Remote and hybrid work has also become permanent, increasing endpoints, identities, and cloud services—and the risk of misconfiguration. MSP leadership now means reducing complexity without slowing the business down. Support alone isn’t enough; MSPs are judged on security maturity, cost predictability, operational discipline, and decision guidance.
The managed services space is no longer only about keeping tickets moving and servers humming. The best providers are being judged on:
This is where Women in IT services are making a visible mark—driving innovation, building resilient teams, and setting new expectations for what managed services can deliver.
If you’re looking for a blueprint of modern MSP industry leadership, Tiffany Bloomsky stands out for one reason: she treats managed services as a business partnership first and a technology function second.
Many providers still measure success mainly through operational metrics: tickets closed, endpoints managed, uptime percentages. Those are necessary, but Tiffany’s approach pushes a step further—connecting service delivery to what clients actually care about: productivity, risk reduction, predictable budgeting, and growth support.
That mindset shows up in how Cortavo positions managed services around practical outcomes:
In short: it’s not support for support’s sake. It’s support that moves the business forward.
One of the biggest friction points in managed services is the “black box” feeling—clients don’t know what’s happening until something breaks, and invoices can feel disconnected from value. Tiffany’s leadership emphasizes the opposite: transparency in what’s being managed, why it matters, and how it supports the client’s goals.
That commitment to clarity matters in a market where trust is everything. When clients can see what’s being done—and understand the “why”—they stay longer, invest more confidently, and collaborate instead of escalating.
SMBs don’t have time for complexity. They need reliable systems, secure operations, and quick answers—without having to build an internal IT department. Tiffany’s focus has been to design managed services that fit how small and mid-sized organizations actually operate: lean teams, busy leaders, and limited tolerance for disruption.
If you want to compare what “good” looks like across the market, this roundup of top managed IT services providers in US is a useful reference point—especially if you’re trying to benchmark service models, coverage, and expectations.
Tiffany Bloomsky is helping reshape what clients expect from managed services: not just reactive support, but a steady operational foundation that makes the rest of the business stronger. That’s the difference between an MSP you “have” and an MSP you genuinely rely on.
Kate Bolseth has helped position HelpSystems as a major player across IT security, compliance, and managed services—areas that increasingly define the “must-have” baseline for MSPs serving growing organizations.
A decade ago, security and compliance were often treated as add-ons. Now they’re inseparable from managed services. Bolseth’s leadership reflects that reality: security isn’t a product you bolt on—it’s a service capability you build into everything, from identity controls to monitoring to response planning.
Bolseth has played a key role in guiding strategic acquisitions, including Digital Defense, strengthening HelpSystems’ SaaS-based security offerings for enterprises. That’s an important leadership signal in the MSP world: the market is moving fast, and leaders who can integrate new capabilities without breaking service quality will outpace those who can’t.
Bolseth’s work highlights a shift in how managed services gets sold and delivered:
This is MSP industry leadership in a form that’s becoming the norm: security-forward, integration-savvy, and built for complexity.
Gina Murphy is a strong example of operational leadership in a managed services environment that’s deeply cloud-centered. As President and COO at Navisite, she oversees portfolio and operations at a managed cloud service provider—right where many mid-market businesses are placing their bets.
Murphy has been pivotal in navigating the transition to cloud-based, customized services for middle-market enterprises, partnering with major providers like AWS and Microsoft. For MSPs, that “customized services” piece is key: cloud is not a one-size-fits-all journey, and clients often need help balancing speed, cost, governance, and security.
In managed services, strategy is only as strong as execution. Murphy’s role emphasizes:
This kind of leadership tends to create a calmer client experience: fewer surprises, clearer outcomes, stronger alignment.
While Navisite often serves larger mid-market organizations, the direction Murphy represents affects everyone downstream. The expectations SMBs have today—cloud readiness, hybrid environments, secure access, modern collaboration—are shaped by what mid-market and enterprise providers normalize.
If you’re evaluating options built for smaller teams, this guide to managed IT services for small businesses lays out what to look for (and what questions to ask) so cloud adoption doesn’t turn into “cloud chaos.”
While Equinix is widely known for data centers and digital infrastructure, Sara Baack’s influence is highly relevant to managed services because infrastructure strategy shapes what MSPs can deliver—especially for hybrid, multi-cloud, and latency-sensitive environments.
Baack has helped shape Equinix’s digital infrastructure strategy with a focus on enabling clients to use interconnected digital services. That matters because the managed services world is increasingly about:
MSPs can’t innovate in a vacuum. The platforms they build on—networking, connectivity, data center strategy, interconnection options—define what’s possible. Baack’s leadership aligns with the infrastructure side of managed services innovation: giving organizations more flexible, interconnected building blocks.
In other words: when infrastructure becomes easier to connect and govern, MSPs can focus more on delivering outcomes and less on fighting limitations.
Baack’s role shows how managed IT service innovators are not only found inside MSPs. They’re also shaping the ecosystems MSPs depend on. That’s a key part of redefining the industry: managed services isn’t a single category anymore—it’s an interconnected stack of capabilities.
Liz Riley’s leadership at Logically speaks directly to the heart of the MSP market: small and mid-sized businesses. Logically has built a strong presence as an MSP focused on SMBs, and Riley has played a major role in aligning services with client business goals.
Many SMBs don’t want a list of tools. They want answers:
Riley’s leadership in aligning managed IT services to business outcomes is a sign of where the best MSPs are going. It’s a move away from “we manage your tech” and toward “we help your business run better through tech.”
Operational leadership matters most where complexity meets scale. Riley’s ability to drive growth while managing professional services and technical teams points to a key MSP challenge: keeping delivery consistent as the organization expands.
That balance—growth without quality drift—is one of the hardest problems in the industry. Leaders who solve it set the pace for everyone else.
Riley’s work reinforces a growing market reality: SMB-focused providers win when they are excellent at the basics (support, monitoring, reliability) while also guiding clients through higher-stakes topics like security, cloud transitions, and standardization.
For businesses comparing options, lists like best IT support companies are popular—but the real differentiator is whether the provider can translate IT activity into business stability and momentum.
Even though these women hold different roles—CEO, COO, CPO, CISO—their impact overlaps in a few clear ways:
That’s what strong MSP industry leadership looks like right now—practical, security-aware, and designed around client success.
Managed services are no longer a “nice-to-have” layer of IT support. It’s becoming the operational backbone that keeps organizations secure, productive, and able to grow without constant disruption. As expectations rise, the leaders shaping this space are the ones who treat service delivery as a business function—measurable, transparent, and built around outcomes clients can actually feel.
The women featured here are redefining MSP industry leadership in different ways, but the pattern is consistent: security is designed in from the start, operational discipline isn’t optional, and client alignment matters as much as technical skill. Whether they’re running MSPs, scaling cloud operations, shaping infrastructure platforms, or leading security programs, they’re influencing what “good” looks like across the market.
For more help benchmarking your options and asking sharper questions, Cortavo’s resources can help you narrow the field:
Tim Conkle is the Founder and CEO of The 20 MSP Group. He’s also widely referenced in the channel as the public-facing executive for The 20.
Most strong MSPs run on the same core principles: proactive monitoring, clear SLAs, security-first delivery, standardised systems, automation where it reduces errors, transparent documentation/reporting, and continuous improvement tied to business outcomes. When those are in place, service becomes predictable for the client and scalable for the provider.
Market sizing varies by source and definition, but major industry trackers put the global managed services market in the hundreds of billions of dollars today, with strong growth projections through the next decade. For example, one estimate values it at about $297B in 2024 and projects ~$330B in 2025, while another estimates ~$401B for 2025.
In HR and workforce management, MSP usually refers to a Managed Service Provider (or Managed Service Program) that runs contingent labour and staffing operations for an employer—often covering supplier management, processes, compliance, and reporting. It’s commonly used for temporary staff, vendor coordination, and spend visibility.