#37 – From the Trenches Building a $3–$5M MSP, CSM Strategy and EOS Execution (Michael Milhouse)

In this episode of From the Trenches on the BMK Vision Podcast, Josh Peterson sits down with Michael Millhouse (President and Co-Founder of BridgePoint Technologies in the Chicago suburbs) for a grounded conversation about what it really takes to build—and stabilize—a $3–$5M MSP. Michael’s story isn’t framed as a “marketing breakthrough.” It’s framed as the hard, practical leadership work that shows up once the business is big enough to strain your old habits, but not yet structured enough to make growth feel controllable.

What makes this conversation useful is that it names the real constraint in the $3M–$5M band: you don’t scale through it by working harder—you scale by building a system that can carry the load without the owner acting as the operating system. That means role separation at the top (sales, service delivery, finance/admin), a deliberate client engagement motion that produces forward-looking initiatives, and a willingness to stop being “the guy” for every relationship. The punchline is simple: clients don’t pay for your heroics—they pay for reliability, and reliability only exists when the business has structure.

If you’re an MSP owner who feels busy but not in control—especially if recurring revenue is growing while margin clarity feels murky—this episode will resonate. And if your client engagement still relies on technical leaders “checking in” instead of a repeatable expansion motion, pair this conversation with BMK’s guide to client engagement strategy from onboarding to QBRs. For an advisory system that connects execution discipline to leadership cadence, explore Vision. And if you’re actively scaling through this stage, BMK’s work with MSPs in the $3–15M+ revenue range maps directly to the challenges Michael describes.

Why does $3M–$5M feel like the MSP “valley of death”?

Short answer: because your old operating model still “works,” but it no longer scales—and the business starts charging you interest on every inconsistency.

Michael describes the whiplash MSP owners feel in this band: you gain ground, slide back, get frustrated, and wonder whether the business is actually improving or just getting bigger. It’s not that growth becomes impossible. It’s that growth becomes expensive when execution discipline hasn’t caught up to revenue.

• Sales can accelerate faster than service maturity
• “Fixing service” becomes a permanent task unless governance exists
• Owner heroics stop being an asset and start being a bottleneck

The MSP problem this episode solves

Many MSPs hit a confusing stage: revenue climbs, the team works nonstop, and the owner still can’t explain why the business feels unstable—or why profitability doesn’t feel as real as it should.

This episode addresses three common growth constraints that show up right as an MSP starts to mature:

• Leadership lanes are blurry, so decisions stall and accountability gets “shared” into meaninglessness
• Client relationships depend on the owner instead of a repeatable account management function
• Execution discipline exists in pockets, not as a company-wide operating cadence

The takeaway is simple: the moment you want predictability, you need structure—roles, rhythms, and standards that keep the business consistent even when people are busy.

Role separation: the least glamorous, highest-leverage growth move

Short answer: scale requires clear ownership across sales, service delivery, and finance/admin—especially when there are multiple partners.

Josh and Michael reinforce a pattern BMK sees constantly: when owners “all do a version of everything,” the business looks collaborative but operates like chaos. Clear lanes reduce founder bottlenecks, stop internal overlap, and create the accountability needed to build a leadership layer beneath the owners.

• Sales/marketing ownership creates a controllable pipeline
• Service ownership creates predictable delivery and quality
• Finance/admin ownership creates clarity, margin control, and operational truth

CSMs and SBRs: turning client engagement into a growth engine

Short answer: treat Customer Success Managers as revenue-generating account managers—and turn QBRs into Strategic Business Reviews that govern the future.

Michael explains how BridgePoint used CSMs to create consistent client touchpoints and expansion motion. The key shift is philosophical: the meeting is not a recap of tickets. It’s a forward-looking alignment conversation—security posture, modernization, cloud initiatives, and the next set of business-aligned recommendations.

• CSMs create repeatability (not “best effort” client engagement)
• SBRs reduce drift and surface initiatives proactively
• Owners can step back without clients feeling abandoned

Financial clarity starts with operational truth

Short answer: you can’t manage margin with blurry categories—and you can’t trust margin if execution data is undisciplined.

Michael is candid about a reality most MSPs face: charts of accounts often exist for tax convenience, not for operating decisions. In the $3–$5M band, that stops working. When you’re running multiple lines of business (managed services, SaaS, custom development), you need clean structure—otherwise you end up arguing with the P&L because it can’t explain the story.

• Segment revenue so margin can tell the truth
• Separate lines of business so expenses land where they belong
• Stop “feeling” profitable—start proving it with reliable reporting

Why EOS works (and why it often fails without a facilitator)

Short answer: because partners rarely hold each other accountable consistently—and execution degrades without an external cadence keeper.

One of the most valuable threads in the episode is Michael’s experience moving from attempted self-implementation to working with a professional EOS facilitator. The change is subtle but decisive: commitments stop being optional, quarterly priorities become real, and communication improves across the organization because everyone can finally see where the company is going.

• External facilitation creates real accountability
• Level 10 rhythms turn issues into owned actions
• Better communication reduces the “owner-head-only” operating model

A practical checklist MSP owners can apply this quarter

If you want to turn the lessons from this episode into execution, here’s a simple checklist to work through:

• Define owner lanes (sales/marketing, service delivery, finance/admin) and make accountability visible
• Install or strengthen a CSM/account management function that is measured and incentive-aligned
• Replace ticket-recap QBRs with forward-looking SBRs that produce initiatives and projects
• Clean up financial structure so revenue and expenses tell the truth by service type / line of business
• Adopt an execution cadence (EOS or equivalent) with facilitation that forces follow-through

These aren’t growth hacks. They are governance disciplines—the kind that make growth sustainable instead of exhausting.

Episode highlights

• 00:01:00 – Michael’s pivot from programming into MSP entrepreneurship and the early mindset shifts that shaped his leadership
• 00:09:00 – Early-stage hustle stories and what it taught him about building pipeline when you have no brand
• 00:12:00 – Why separating ownership of sales, service delivery, and finance prevents overlap, confusion, and stalled growth
• 00:18:00 – How CSMs became revenue-generating account managers (not just relationship maintenance)
• 00:25:00 – Turning QBRs into Strategic Business Reviews that focus on what’s next—not what already happened
• 00:43:00 – The $3–$5M “valley of death” and the leadership shift from doer to strategic operator
• 00:51:00 – Implementing EOS with a facilitator to build accountability, cadence, and leadership alignment

About the guest: Michael Millhouse

Michael Millhouse is the Co-Founder and President of BridgePoint Technologies, an MSP based in the Chicago suburbs that provides managed and co-managed IT services, cybersecurity, cloud solutions, and IT strategy. Michael’s leadership perspective is rooted in a rare combination: technical beginnings, sales and account management maturity, and the operational discipline required to build a business that can scale beyond the owner’s calendar.

Connect with Michael on LinkedIn →

Frequently asked questions

What typically breaks in an MSP between $3M and $5M?
Role clarity and execution cadence. The business outgrows informal habits, and inconsistencies in service governance, accountability, and client engagement become expensive.

Are Customer Success Managers worth it for a growing MSP?
Yes—when the role is treated as a measurable account management function that drives retention and expansion, not as a vague “client happiness” role.

What’s the difference between a QBR and a Strategic Business Review (SBR)?
QBRs often look backward. SBRs align forward: business goals, risk posture, initiatives, and the next sequence of work that produces outcomes.

Why does EOS fail when MSPs try to self-implement?
Because accountability weakens without an external facilitator. Meetings drift, commitments become optional, and the cadence turns into activity instead of execution.

Why do MSP financials feel unclear even when revenue is up?
Because categorization and segmentation are often built for tax reporting, not operational decisions. Without clean structure, you can’t reliably see where margin is created—or lost.

How do I stop being “the guy” without losing client loyalty?
Build a repeatable account management motion, introduce it intentionally, and stay present strategically (not reactively). Clients don’t need the owner—they need consistency.

Related resources from Bering McKinley

• The role of MSP financial consulting in revenue growth
• 3 key project indicators driving MSP profitability

Want to continue the conversation?

If you’re building through the $3M–$5M ceiling and want help connecting leadership lanes, client engagement, and execution discipline to financial clarity, explore Vision or apply to be a guest on the podcast.

👉 Apply to be on the BMK Vision Podcast
👉 Learn more about Vision

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