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Expertise in Lower middle market M&A
Clarity in the Deal. Strategy Beyond It.
Focused on companies with $500k to $5m of EBITDA, Cayne Crossing provides diligence and financial leadership to help entrepreneurs make smarter acquisitions and build enduring companies.
Team focused on Your Success
Our Process
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About Cayne Crossing
Built by Operators. Trusted by Entrepreneurs.
At Cayne Crossing, we combine deep M&A experience with real-world operational insight to help entrepreneurs buy, grow, and lead businesses with confidence. Our team has advised on hundreds of acquisitions, invested across industries, and provides the financial partnership needed for long-term success.
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Median enterprise value
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Clients serviced in 2025
One Team. Every Side of the Table.
Learn more about our team
Smarter Due Diligence
Quality of Earnings You Can Trust
Buying or selling a business? A Quality of Earnings (QofE) analysis is one of the most important steps you can take. It goes far beyond a simple review of financial statements—helping you uncover what’s really driving profitability, cash flow, and risk.
At Cayne Crossing, we approach QofE with the same rigor we learned at the Big 4, scaled to match the size of your deal. We dig into customers, vendors, employees, and bank data to reconcile what’s happening in the numbers with what’s happening in the business. The result? Clarity you can count on when making a major decision.
our Investments
Where We’ve Invested — and Why
We partner with searchers and small business operators to invest in businesses that are built to last. From landscaping and logistics to solar and food distribution, each investment reflects our hands-on approach, rigorous diligence, and long-term commitment to supporting exceptional entrepreneurs.
Our Services
What We Do
Our services are shaped by experience. We don’t just check boxes — we solve problems, close gaps, and move deals forward.
Our Process
A Smarter Way to Partner
From first call to post-close, our process is built to reduce friction, uncover value, and help you succeed long after the deal is done.
01
Understand the Opportunity
We dig in early — learning your goals, the business, and the deal dynamics to build a clear roadmap.
02
Analyze & Advise
From quality of earnings to tax diligence and structuring insights, we provide focused analysis and practical guidance.
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Stay Involved
Post-close, we offer working capital and opening balance sheet support and ongoing outsourced accounting & tax compliance.
Testimonials
Voices from the closing table
While every transaction is different, the feedback we hear is consistent. Our clients value insight, responsiveness, and having a partner who’s been in their shoes.
SaaS Acquisition
Smart, responsive, and experienced. I’d work with Cayne Crossing again in a heartbeat.
PE Firm
As a small business owner, I was struggling to make sense of complex financial data. Cayne Crossing not only provided clarity but also helped me streamline my accounting processes, saving time and money!
SMB
They didn’t just point out problems — they helped us solve them. Their team was a true extension of ours.
Logistics Business
I was overwhelmed heading into the deal. Cayne Crossing helped me stay focused and make confident decisions.
First-Time Buyer
Their team knows small businesses. They understand the numbers — and the people behind them.
Sell-Side Engagement
Thinking about buying a business?
Let’s talk. We’ll help you understand what’s out there, what’s possible, and how to make your next move a smart one.
Cayne Crossing is a financial partner to entrepreneurs and investors, helping them acquire, grow and sell lower middle market companies.
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Note: Cayne Crossing employs CPAs but is not a licensed CPA firm.
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Cayne Crossing brought clarity to a complex acquisition. Their diligence work was sharp, and their advice was practical every step of the way.