#45 – From the Trenches: Enterprise Roots, AI Strategy & MSP Fundamentals (Corey Kirkendoll)

In this episode of From the Trenches on the BMK Vision Podcast, Josh Peterson sits down with Corey Kirkendoll—an enterprise-trained MSP operator who can translate both “boardroom” and “server room”—for a leadership-level conversation about what’s changing in the MSP market, what’s not, and why fundamentals are about to matter more than ever.

This is not an AI hype episode, and it’s not a tool discussion. It’s a conversation about maturity: the discipline to run your MSP as a measurable service business, the humility to treat relationships as a strategic advantage, and the clarity to understand that automation and AI don’t fix broken operations—they accelerate them. Corey lays out a simple but rare mindset: if your PSA is “just a ticketing system,” you’re not managing a business; you’re documenting activity. Real leadership starts when you can see profitability, utilization, and customer outcomes clearly enough to make hard decisions with confidence.

If you’re an MSP owner trying to reconcile AI opportunity with security reality, struggling to move clients beyond “table stakes” IT support, or feeling the tension between growth and control, this episode will resonate—because it’s ultimately about stewardship: building an MSP that is durable, measurable, and hard to unseat.

Why the “enterprise mindset” is an MSP advantage

Corey’s origin story matters because it explains his operating posture. He didn’t stumble into managed services from the help desk—he came through enterprise environments (IBM, Cisco, Dell, EMC), then layered on an MBA that trained him to think in budgets, ROI, and business outcomes. That combination creates an uncommon advantage in MSP leadership: the ability to speak in outcomes to executives without losing technical credibility with engineers.

• Executive alignment: “Tell me how your business is doing… how does the money flow?” is a different conversation than “How’s the network?”
• Positioning leverage: When you can articulate outcomes, your MSP stops being interchangeable.
• Operational clarity: Metrics become leadership tools, not accounting artifacts.

Table stakes are real—so what do MSPs sell now?

One of the most useful through-lines in the episode is this: the core things MSPs spent a decade perfecting—access, uptime, “generally secure,” email and connectivity—are increasingly assumed. Clients don’t celebrate them; they expect them. That doesn’t mean your work is less important. It means your differentiation has moved up the stack.

The winning posture is advisory leadership: connecting technology decisions to measurable outcomes, productivity, risk reduction, and business performance. In Corey’s framing, you’re in a relationship business that happens to deliver IT. That relationship orientation is not soft—it’s strategic, because trust and understanding are what make you “hard to unseat.”

AI is not a feature—it's a governance problem first

The episode’s most practical warning is also the most urgent: AI tools can create value quickly, but they can also leak data quickly—especially when MSPs (or clients) turn on co-pilots without foundational controls. Corey’s point is simple: if sensitive information is already accessible through poor permissions and weak controls, AI doesn’t create the vulnerability—it amplifies it.

• Harden first: conditional access, security baselines, and data governance are prerequisites.
• DLP matters: data-loss prevention becomes non-negotiable when AI accelerates discovery and exposure.
• Policy + legal clarity: AI usage has emerging compliance, HR, and liability implications—especially where biased outcomes can create real risk.

This is exactly why disciplined client engagement and financial visibility matter: MSP owners need a repeatable cadence that supports executive conversations and defensible decisions. For related guidance, revisit BMK’s perspective on building a structured client engagement strategy from onboarding through QBRs and the financial consulting MSPs need to grow profitably.

The hidden MSP profit leak: fundamentals you can’t “AI” your way around

What makes this episode unusually grounded is where it lands: back on fundamentals. Corey and Josh connect AI strategy to the unglamorous operating discipline most MSPs underinvest in—time entry integrity, ticket hygiene, utilization, and profitability by customer. Because those inputs are what let a leader run a business instead of reacting to noise.

Without reliable data, leadership becomes guesswork:

• You can’t defend pricing—or know which clients are actually profitable.
• You can’t rationally hire—because workload perception replaces utilization reality.
• You can’t improve service—because you can’t see first-time resolution, rework, or where friction originates.

Corey’s framing is blunt and useful: if you want the owner to make good decisions, you must give them clean inputs. That’s not micromanagement—that’s operational stewardship.

Automation doesn’t fix broken processes—it amplifies them

Josh raises a common hope: that automation should be rolling out faster to clients. Corey’s response is the corrective most MSPs need: if your process isn’t written down and repeatable, automating it simply scales the dysfunction. The ordering matters:

• Policy first: define the “rules of the road” and the expected standard.
• Procedure next: document how work gets executed consistently.
• Automation last: then amplify what already works.

That sequencing is not bureaucracy—it’s what turns an MSP into an asset that can scale, train new leaders, and operate without heroic effort.

Learn More: For MSPs building operational discipline alongside advisory leadership, explore these related articles: how to build profitable service agreements, supporting your service team by hiring a dispatcher, and improving MSP financial operations through better data.

Return to the BMK Vision Podcast main page →

Listen on Your Favorite Platform

Episode Highlights

• 00:01:00 – Reframing change as opportunity—how data and curiosity help MSPs see disruption as a chance to improve outcomes.
• 00:05:24 – Lessons from Australia: why relationships must come before transactions in any sustainable MSP model.
• 00:09:51 – Applying an agile, MVP mindset to MSP services: delivering the most present value to clients this week, not someday.
• 00:15:07 – Positioning AI as a productivity amplifier for employees and clients rather than a replacement for human roles.
• 00:18:36 – The security imperative: hardening environments and implementing DLP before rolling out co-pilots and other AI tools.
• 00:37:04 – Why automating broken processes only magnifies pain—and how to get back to basics with policies and procedures first.
• 00:49:36 – Using accurate time and profitability data to make tough calls about unprofitable customers and resource allocation.

Frequently asked questions

How should MSPs position AI services without creating security risk?
Treat AI as a governance and data-control initiative first: harden environments, implement DLP, define access boundaries, and then deploy co-pilots and assistants inside guardrails.

What is DLP and why does it matter for Copilot and AI assistants?
DLP (data loss prevention) reduces the risk of sensitive information being discovered, exposed, or exfiltrated—especially when AI accelerates search, summarization, and content generation across files and systems.

Why do MSP fundamentals still matter in an AI-driven era?
Because leadership decisions rely on clean inputs: time entry, utilization, ticket hygiene, customer profitability, and resolution data. AI can’t compensate for missing or unreliable operational data.

What does “policy before procedure before automation” mean for an MSP?
It means you define standards first (policy), document consistent execution second (procedure), and only then automate—so you scale what works instead of scaling dysfunction.

How do MSPs monetize AI strategy work without forcing everything into recurring revenue?
Start with an assessment and roadmap as a project, then convert to a retainer model for ongoing governance, training, model maintenance, and continuous improvement as tools and models evolve.

What makes an MSP “hard to unseat” today?
Being embedded as a trusted advisor: understanding the client’s business model, aligning IT to outcomes, and running a consistent cadence of planning, review, and accountability—so you’re tied to results, not tickets.

Related resources from Bering McKinley

• Learn more about the BMK Vision platform
• Client engagement strategy for MSPs: from onboarding through QBRs
• The role of MSP financial consulting in revenue growth

About the Guest

Corey Kirkendoll is the President and CEO of 5K Technical Services, a Dallas-based managed service provider known for combining enterprise-grade discipline with practical small and midsize business outcomes. With an MBA and deep technical credentials that include certifications such as CISSP and CCIE, Corey is equally at home talking to technicians about architectures and to executives about budgets, risk, and ROI. He has built his MSP around data-driven management, using metrics like utilization, first-time resolution, and customer profitability to guide hiring, client selection, and service design.

Corey is an early advocate for weaving AI and automation into everyday MSP and client workflows—but only on top of strong fundamentals. He helps organizations document and refine their policies and procedures before automating them, ensuring that tools like co-pilots, AI assistants, and advanced analytics amplify good processes rather than broken ones. As AI Strategy Providers (AISPs) emerge as a new niche, Corey is focused on positioning MSPs to collaborate with those firms, own their role in securing and governing AI, and stay at the center of their clients’ most important technology and business conversations.

🌐 Connect with Corey on LinkedIn →

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through the From the Trenches series, Josh highlights MSP leaders who redefine growth through creativity, resilience, and genuine client connection.

🌐 Connect with Josh on LinkedIn →

📺 Subscribe on YouTube →