Lower Middle Market Advisory

Better M&A Advisory for Business Owners

We bridge the gap for businesses with $5M to $100M in revenue.

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Better Buyers
Focused Strategic Outreach Combined with Broad Market Matches.
4x Higher Close Rate
Four times higher close rates than the industry average
Higher Offers
Competitive auction process vs. responding to proprietary buyer outreach

A New Approach to Selling Your Business

Lower middle market businesses between $10M and $100M in revenue are underserved by traditional business brokers and investment banks who have been slow to adapt technology to make transactions faster, more valuable, and easier for business owners. Our clients are too large for traditional business brokers, who often lack the sophistication to run a proper process. But they're too small for investment banks, where large deal teams and minimum fees make the economics challenging.

We founded Trailhead Partners to bridge that gap. As former business owners who have started, acquired, operated, and sold companies ourselves, we understand what you're going through. That experience shapes how we advise - with empathy, honesty, and practical insight.

Operator Experience

We've started, bought, and sold our own businesses.

Honest Guidance

We tell you what you need to hear, not what you want to hear.

Process Excellence

Disciplined process creates better outcomes.

Aligned Incentives

We succeed when you succeed.

Track Record

Recent Transactions

We advise owners through successful exits across industries.

Client Feedback

What Our Clients Say

"Zach and Drew provided steady guidance from the very beginning. They took the time to understand our priorities and explained how to do this. I had never sold a business before so they walked me through valuation, due diligence, and every other step along the way."
Confidential Owner
Founder
Service Company
"The guys at Trailhead were trustworthy, diligent and transparent. They did what they said they would do and I'm thankful to have partnered with them to find the right buyer to continue the legacy of this business."
Tony Del Plato
Founder
Maktech Fleet Services
"We felt supported, informed, and confident throughout the entire journey. Most importantly, they were thoughtful in how they represented our company to potential partners."
Business Owner
President
Service Business
For Sellers

Buyers like exclusivity. We like options.

We're market builders.

You're hounded by individual buyers and private equity groups who want to take a closer look at your business. You've probably received unsolicited offers to purchase, each claiming they pay "top dollar."

There are thousands of investors who want a piece of successful businesses. Don't settle for the buyers in your inbox.

Trail Notes

news

Deal Closing Announcement: Maktech Fleet Services

Trailhead Partners is pleased to announce the acquisition of Maktech Fleet Services, a commercial fleet maintenance company located in Melissa, TX, by East Fork Trinity Partners, led by Brian Baklenko.

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quick hits

Letter of Intent Details Matter

Ambiguous Letters of Intent kill deals. They're a waste of time for both sides and bring consequences for sellers far in excess of the hard costs spent on the transaction.

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perspectives

Selling a Business is Hard

Selling a business can be messy and stressful, no matter the size. At Trailhead, we've sat in the shoes of buyers and sellers and know firsthand what the experience is really like.

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Ready to Start the Conversation?

Whether you're considering a sale, exploring options, or just want to understand your business's value - we're here to help.

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