Headway Invesments
Fundamental Growth Through Practical Improvement
Who We Are
We are entrepreneurial business investors with deep roots in business operations and a proven track record of building successful teams and processes. We bring hands-on experience from leadership roles across a range of industries, giving us a unique perspective on what it takes to grow sustainable, high-performing businesses. We actively partner with stakeholders to drive strategic growth, operational excellence, and long-term value creation. Our approach is grounded in a shared passion for entrepreneurship, a commitment to integrity, and a belief in the power of collaboration.
What We Believe
We believe that the foundation of lasting business success lies in strong relationships and thoughtful, collaborative execution. We partner closely with business owners, employees, customers, and key stakeholders to build trust and alignment around a shared vision. Our approach emphasizes practical, data-driven improvements that unlock growth, enhance operational efficiency, and strengthen organizational culture. We are firm believers in fundamentals — not quick fixes — and we work side by side with teams to implement strategies that are sustainable, measurable, and tailored to the unique needs of each business. At our core, we believe in creating value through integrity, transparency, and mutual respect
Investment Criteria
We seek to acquire stable, scalable companies in the lower middle market that demonstrate consistent performance and clear potential for long-term growth. Our ideal targets have a strong foundation—proven business models, recurring or repeatable revenue streams, loyal customer bases, and opportunities for operational enhancement. We typically focus on companies with annual EBITDA of $1 million or more, where our strategic and operational expertise can help unlock untapped value. We are industry-agnostic but particularly drawn to businesses with durable competitive advantages, capable management teams, and a culture aligned with our collaborative, hands-on approach to value creation.