#75 – From the Trenches: Copier-to-MSP Scale, AI Ops & Family-Business Leadership (Jocelyn Gorman – DSI)

In this episode of From the Trenches on the BMK Vision Podcast, Josh Peterson sits down with Jocelyn Gorman of DSI for an unusually practical leadership conversation about a path many MSP owners underestimate: scaling from a copier-dealer “mothership” into a consultative, SMB-first managed services business—without losing focus, culture, or profitability. Jocelyn’s story is a case study in building leverage through operating systems: sharpening go-to-market segmentation, designing incentives that drive team selling, and using execution frameworks to keep growth from turning into chaos. If you’re working through the “what do we keep, what do we stop, and what do we standardize” season of scale, her lens pairs well with BMK’s guidance on sustainable MSP growth—and it sets up a grounded way to think about AI in the MSP without chasing shiny objects.

This is not a conversation about “copier clients are free MSP leads” or other comfortable myths. Jocelyn is candid about the real numbers: only a slice of the copier book is truly a fit for managed services, and the sales motion changes completely once you stop trying to make generalists do everything. The bigger insight is the leadership trade: cash-flow-heavy contracts can fund capability, but they can also mask margin problems if you confuse revenue with health. From there, the episode moves into what “AI ops” actually looks like in a mid-market, family-owned operator—less about replacing humans, more about compressing cycle time, documenting processes before automating them, and building internal champions so your tools don’t become permanent dependencies.

If you’re an MSP owner wrestling with positioning, pricing pressure, or the transition from technician to business leader, this episode will resonate.

How do you scale from copier roots into a durable MSP?

Short answer: you scale by separating credibility from capability—and then engineering the operating model that turns credibility into repeatable value.

A copier dealership can give you brand recognition, infrastructure, and a sales engine—but it doesn’t automatically give you MSP positioning, MSP delivery maturity, or the consultative muscle required to win profitable SMB contracts. Jocelyn describes the pivot as a deliberate narrowing: choose the client profile you can serve best, build a service model that produces margin, and stop assuming your legacy book will do the hard work for you.

In other words, the win is not “we added managed services.” The win is “we built a managed services business with its own focus, roles, and standards—while still benefiting from the broader platform.”

• Use the parent brand to reduce early risk—but don’t let it define your MSP identity
• Optimize for many profitable contracts, not impressive revenue that hides weak margins
• Segment sales roles and incentives so managed services is sold on outcomes, not attachments

The MSP problem this episode solves

Many MSP owners are caught in a confusing middle: they have enough demand to stay busy, but not enough structure to scale cleanly. They accumulate tools, add headcount, and chase bigger contracts—yet still feel fragile because profitability depends on a few hero performers and a few oversized accounts.

This episode addresses three common MSP challenges:

• Revenue growth that improves cash flow but doesn’t improve profitability
• Generalist selling that spreads the team thin and makes performance inconsistent
• Automation efforts that fail because process discipline and adoption aren’t in place

Jocelyn’s operating stance is a helpful corrective: first get clarity on the business you want to be, then align roles, process, and systems so the organization can execute without constant improvisation.

Cash flow vs. profitability in MSP scaling

A cash-flow-first growth pattern often competes on:

• Large staff-augmentation style contracts
• High headcount to meet coverage requirements
• Custom work that is hard to standardize
• Revenue optics that can hide true margin

A profitability-first MSP model competes on:

• Tight ICP and contract discipline
• Consultative value that earns premium pricing
• Repeatable delivery standards that reduce variance
• Operational leverage through process + automation

Jocelyn explains the nuance well: the early “big contract” can be the runway you need—so long as you treat it as financing for capability, not as proof that the model is healthy.

AI ops without the hype

The most useful framing in this episode is that AI is a force multiplier, not a personality. It can compress time, reduce administrative drag, and elevate managers—but only when the underlying work is understood and owned.

• Document the process manually before you automate it
• Create internal champions who can iterate as tools change
• Start with narrow, high-friction tasks (RFPs, coaching, data entry)
• Avoid paying for “AI magic” you could learn to operate yourself

That orientation keeps AI from becoming a distraction. It also reframes the real constraint for most MSPs: not technology access, but the leadership discipline to drive adoption and to keep improving the system after go-live.

Family-business leadership as an operating system

Family business adds a unique layer of tension to MSP scaling: credibility can be inherited, but trust inside the organization still has to be earned—and governance has to survive normal human dynamics. Jocelyn’s story highlights a few leadership mechanics that translate to any MSP, family-owned or not.

• Earn credibility through measurable roles before you inherit authority
• Design clear accountability so “family” doesn’t override standards
• Build managers through coaching systems, not hope and heroics
• Use incentives to drive cross-team behavior without creating chaos
• Limit concurrent change so culture can absorb what strategy demands

The takeaway for MSP owners is simple: culture is not what you say. It is what your systems reward, what your managers tolerate, and what your execution cadence makes inevitable.

Episode highlights

• How a first, oversized medical contract funded the MSP build-out (and what it did—and didn’t—prove)
• Why only a portion of a copier client base is a true managed-services fit
• The inflection point from generalist reps to dedicated MSP sales roles
• What “AI as a calculator for work” looks like in RFPs, coaching, and operational analysis
• Why process mapping comes before automation—and how to avoid tool sprawl

About the guest: Jocelyn Gorman

Jocelyn Gorman leads DSI, a family-owned technology company based in Albuquerque, New Mexico, with multiple offices across the state. She built DSI’s managed services business from the ground up, bringing a sales-led, systems-first approach to SMB consultative IT and operational leverage through process, automation, and disciplined execution.

Connect with Jocelyn Gorman on LinkedIn →

Frequently asked questions

Can copier dealers really become strong MSPs?
Yes—but only when they stop treating managed services as an “add-on” and build it as its own business unit with dedicated delivery standards, a clear ideal client profile, and a consultative sales motion. The copier brand can help with trust and market presence, but it won’t replace MSP maturity.

Why don’t copier client books convert into MSP contracts at a high rate?
Because fit is narrower than most teams assume. Some accounts aren’t sized correctly, some aren’t operationally ready for MSP-style change, and many “copier relationships” were built on a different value exchange than advisory IT. Expect a subset to be ideal and design your go-to-market accordingly.

What’s the leadership trap with “big contracts” in MSP land?
Large staff-augmentation or coverage-heavy deals can create cash flow without creating a healthy operating model. If you confuse revenue with health, you’ll scale complexity faster than capability. Treat early big contracts as runway—then build toward repeatable, profitable SMB agreements.

How should MSP owners think about AI and automation right now?
As leverage, not identity. The best early wins are narrow and measurable: compressing time on writing, analysis, coaching, and administrative work. The prerequisite is process clarity—if the workflow is undefined, automation typically just accelerates confusion.

Build or buy AI tools—what’s the right call?
Hybrid is usually best. Buy where it’s commodity, build where it’s differentiating, and always ensure someone internally can operate and evolve the capability. If you can’t tune it, maintain it, or iterate on it, it will become a dependency instead of leverage.

Learn more

Here are a few supporting resources if you want to go deeper on the underlying themes discussed in this episode—positioning, operational leverage, and building an execution system that scales.

• Vision: BMK’s operating system for MSP leadership and execution
• MSP consulting services that help you lead, scale, and win
• Managed service provider consulting: your partner for MSP excellence

Want to continue the conversation?

If you’re an MSP owner building toward a blue-ocean future—and want help creating clarity, discipline, and execution—explore the Vision operating system or apply to be a guest on the podcast.

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