Gary Strickland brings together strategic finance and hands-on operational leadership.
He’s a senior financial executive with a track record of driving performance and enterprise value in growth-oriented technology and services businesses. With more than three decades of experience leading and advising founder-led, venture-backed, and PE-owned companies, Gary has become a trusted strategic partner to CEOs navigating high-growth, capital-intensive, and complex environments.
As Managing Partner of TechCXO’s Boston office and fractional CFO with 18 years at the firm, Gary leads from the front, combining deep technical finance expertise with hands-on operational engagement. He doesn’t just advise; he embeds, aligning strategic intent with execution and ensuring capital, talent, systems, and performance metrics stay in sync from boardroom to front line.
Gary specializes in working with technology-centric businesses across SAAS, healthcare IT, telecommunications, professional services, and financial services. His core value lies in helping companies evolve from early-stage to growth-ready, and from growth-ready to exit-prepared. He often operates across both finance and operations, integrating the two to drive measurable, sustainable business outcomes. His approach is analytical, yet delivery-oriented; governance-minded, yet growth-focused.
He is particularly adept at working within the complexity of institutional capital, having supported dozens of companies backed by angel investors, venture capital, and increasingly, private equity. Gary brings hard-won experience from both sides of the table, having raised hundreds of millions in capital and having led organizations through IPOs, M&A, and transformation scenarios.
Key areas of impact include:
- Serving as a trusted strategic and operational advisor to CEOs and boards
- Scaling companies from founder-led to institutional-grade
- Driving performance through aligned financial and operating disciplines
- Leading capital formation, recapitalizations, and exit planning initiatives
- Building infrastructure for international expansion, compliance, and scalability
Before joining TechCXO, Gary served as CFO of SunGard BancWare, where he helped scale a software business unit from $20M to over $60M, and took ZipLink public on NASDAQ. Earlier in his career, he held leadership roles at AP Engines, GammaGraphX, and M/A-COM, and began his career in Ernst & Young’s Entrepreneurial Services Group.
A Certified Public Accountant, Gary graduated cum laude from the University of Notre Dame. His leadership style blends intellectual rigor with operational intensity, making him a vital catalyst for companies aiming to scale smart and build for long-term value.