By: Elena Mart

In the hushed corridors of lower middle-market mergers and acquisitions, a fundamental shift is occurring in how founders approach the sale of their life’s work. Jeff Barrington, Managing Director at Windsor Drake, has emerged as a leading voice in this transformation, advocating for a methodology that prioritizes strategic positioning over raw valuation metrics.

“The traditional approach to selling a business often fails founders at their most critical juncture,” Barrington observes from Windsor Drake’s offices. “Too many advisors focus solely on EBITDA multiples while ignoring the strategic elements that create premium valuations.”

This perspective stems from Barrington’s extensive experience guiding founder-led businesses through complex transitions. Unlike the volume-driven approach of larger investment banks, Windsor Drake has built its reputation on a boutique model that emphasizes deep industry knowledge and personalized advisory services.

The firm’s methodology begins months before any potential buyer is approached. Windsor Drake works with founders to identify and enhance the strategic assets within their businesses that traditional financial analysis might overlook. These include proprietary processes, customer relationships, and market positioning that can significantly impact final sale prices.

“A recent transaction in the specialized manufacturing sector illustrates this approach perfectly,” Barrington explains. “The company showed solid but unremarkable financial metrics. However, by repositioning their proprietary technology as a platform for industry-wide adoption, we transformed buyer perception and achieved a valuation 40% above initial expectations.”

This strategic repositioning represents more than financial engineering. Windsor Drake’s process involves comprehensive analysis of market trends, competitive dynamics, and buyer motivations. The firm maintains relationships with over 500 strategic and financial buyers globally, allowing for targeted outreach that maximizes competitive tension.

The current market environment has made this approach particularly relevant. With interest rates stabilizing and private equity dry powder at historic highs, buyers are increasingly selective. They seek businesses with clear strategic advantages rather than merely acceptable financial returns.

“Founders often underestimate the value of their institutional knowledge and market relationships,” notes Barrington. “Our role is to articulate these intangible assets in terms that resonate with sophisticated buyers.”

Windsor Drake’s track record supports this philosophy. The firm has completed transactions across diverse sectors including technology, healthcare services, and specialty manufacturing, with deal values ranging from $10 million to $150 million. In each case, the emphasis on strategic positioning has yielded results that exceed traditional market comparables.

Looking ahead, Barrington sees continued evolution in the lower middle market. “The next generation of successful exits will belong to advisors who understand both the art and science of dealmaking. Pure financial analysis is table stakes. The real value lies in crafting narratives that capture a business’s true potential.”

For founders contemplating their eventual exit, this shift in approach offers both challenge and opportunity. The challenge lies in beginning the strategic planning process early enough to maximize value. The opportunity comes from working with advisors who see beyond the numbers to the strategic assets that sophisticated buyers truly value. Those attempting DIY approaches or engaging traditional advisors often discover too late that they’ve left significant value unrealized.

About Windsor Drake

Windsor Drake is a premier middle-market investment bank specializing in mergers and acquisitions advisory for founder-led businesses. The firm applies institutional M&A discipline typically reserved for $500M+ transactions to businesses in the $10M–$150M range. With offices in New York, Toronto, and London, Windsor Drake serves founder-led companies across North America and Europe. Learn more at www.windsordrake.com

Disclaimer: This article is for informational purposes only and does not constitute financial, legal, or investment advice. Readers should consult with qualified professionals before making any business decisions.