You’ve Seen One DSO, You’ve Seen One AI Playbook

Let me be clear:
I would never pretend to be a software engineer or act like I know what it’s like to live in that world.

But I did ask a prominent engineer recently—how much actual coding are engineers even doing these days?

Any guesses?

What I learned: about 90% of it is AI-assisted. The engineers who are thriving today aren’t just heads-down coders. They’re great with tools. Great at checking. They move fast. They know how to build with AI—not around it.

And That Got Me Thinking About Dentistry

I’m not in the trenches writing code. But I am spending every day inside the workflows, pain points, and vendor chaos that DSOs are navigating.

And what’s clear is this: we’re in the middle of a technological revolution, and most of us still aren’t treating it that way.

Here’s what I’ve seen lately—some new, some just reinforced:

➡️ AI is transforming dental operations — from insurance verification and call analysis to diagnostics and task management.
➡️ But the landscape is fractured — Two tools for RCM. One for missed calls. One for the front desk. Another for procurement.
➡️ Consolidation is slipping — The very standardization DSOs are chasing is being undercut by disconnected AI tools — if in fact the DSO is embracing the technology.
➡️ Legacy vendors can’t keep up — If you're staying in their lane, you're likely missing the real innovation happening with smaller, faster-moving teams.

So What’s the Move?

You can’t just “slap AI” on everything and call it a strategy.

What’s working in my view?

➡️ Customization. Build with your vendors or your own team—solutions tailored to your workflows.
➡️ Start small. One or two high-value use cases.
➡️ Prove success. Get wins, build momentum.
➡️ Scale smart. Automate what matters. Avoid bloat.

Because here’s the thing we ALL know:
👉 “When you’ve seen one DSO, you’ve seen one DSO.”

There’s no copy/paste AI strategy. But there’s real opportunity to systemize, scale, and do more with less—if you’re intentional about how you build.

🧭 Final Thought

This is what I’ve been learning and thinking about lately through working with AI startups and visiting where the revolution is happening in Silicon Valley.

If you're not already having these conversations inside your org, you should be.
If you are, let’s compare notes.

Because those who lean in now?
They’ll be the ones who build better, faster, and with more clarity—while the rest try to catch up.

Recent Moves

Startup Road Show

I spent some time in San Francisco this month, and the takeaway wasn’t so much something new—it was a powerful reinforcement: If you want to build world-class software, you need to be in the tech capital of the world.

The talent is there. The energy is unmatched. But breaking through to dental? That’s another story.

It raises a bigger question: As Silicon Valley founders get flooded with capital, are they truly building with DSOs in mind—or just chasing the next big exit?

My thoughts on the Silicon Valley energy.

LinkedIn HQ with some tight security inside.

Breakfast of Champions

Once a quarter, I sit down for breakfast with two people I deeply respect—both personally and professionally. Vince Dilley, CEO of Platinum Dental, and Eric Roman, a clinician, former operator, and sharp voice in the industry.

We call it the Breakfast of Champions—and this one didn’t disappoint. Our conversation covered a lot of ground, but for the purpose of this newsletter, let’s zero in on one topic: AI.

Where is it headed? How should DSOs and clinicians prepare?

Here’s a quick look at what came out of the discussion.

The fellas in the new DSO Compass Merch!

Crossing Worlds: From DSOs to Real Estate

Spent some time at Inman Connect recently. What is it, you ask? Think of it as the Dykema of Real Estate—a gathering place for all of us real estate weirdos to network, share ideas, and sharpen our edge.

The parallels to healthcare and dental were striking. One theme stood out: AI. Not in the abstract—but in the workflow. Have a process? Build an agent to support it.

Simple idea. Huge implications.

It was refreshing to step into a different industry, see the same tech push from a new angle, and come back with a few sparks flying in the brain.

Shauntelle and I fueling up for the afternoon.

On the Move and On the Mic

Heading to Dykema with a few resources in hand:

  • A practical AI strategy guide for DSOs

  • A one-pager on tech stack priorities

  • Key questions to help separate real AI solutions from the noise

Let me know if you want to connect or schedule some time here!

Podcast Spotlight: Dental Disruptors

I joined Jake and Clint on the Kola Crew’s Dental Disruptors podcast for a fun, wide-ranging conversation—from Jake not knowing who I was years later… to a deep dive on where the dental industry is heading.

  • Why DSOs don’t need another sales pitch—they need trusted, objective partners

  • The story behind founding DSO Compass

  • How to cut through vendor noise and evaluate tech that actually solves problems

👉 Check it out here.

LinkedIn Newsletter Roundup: July Edition

The Pilots Dilemma — Why tech pilots crash and how to engineer a rollout that actually sticks. It’s not flashy features. It’s about systems that drive consistent EBITDA growth.

What Dental Tech Buyers Overlook: Proximity as Due Diligence — A firsthand look at why being closer to the builders leads to better decisions, stronger teams and smarter tech stacks.

Industry Highlights

Heartland Dental hit with class action lawsuit over AI use. The lawsuit, filed July 3, covers all U.S. residents who made or received a phone call to or from Heartland Dental or a Heartland Dental-managed clinic that was processed by RingCentral. A jury trial was requested for the case.

A more than $18.4 million settlement will resolve a class action lawsuit against Aspen Dental Management over its allegedly illegal use of data-tracking tools on its website.

Why LLMs demand a rethink of healthcare AI governance. The introduction of Large Language Models (LLMs) and Generative AI to healthcare has created a new set of governance challenges that have rendered traditional approaches inadequate.💰

Quick Book Recommendation

Just started reading The Technological Republic: Hard Power, Soft Belief and the Future of the West. It’s a thought-provoking look at how Silicon Valley has drifted from national purpose.

It’s easy to build another photo-sharing app—but much harder to focus on the deeper work of improving our country. This book challenges that mindset and pushes tech leaders to think beyond consumer convenience toward civic responsibility and strategic impact.

DSO Compass: Off Script Podcast Drop

Episode 1:

Running the Dental Offense: Clayton Russell’s Journey from QB to Operator
How sports, structure, and strong routines shaped a calm and consistent DSO leader.

In the first episode of DSO Compass: Off Script, I sit down with Clayton Russell to unpack his journey—from quarterback to dental operator. We cover a lot of ground: the influence of sports and family, the structure that shaped his leadership style, and his take on the evolving dental landscape, including the role of AI.

This episode offers a behind-the-scenes look at one of the industry’s steady voices—and delivers actionable insights for anyone navigating growth, leadership, or change in the DSO world.

Watch or Listen on YouTube and Spotify!

Truly appreciate you being here. See you at Dykema.

Have ideas, questions, or tech you want me to explore? Just reply and let me know.

- Matt

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