Mr Robert Henderson Mr.

Rob Henderson is the Partner-in-Charge of Advisory Services at Windes, where he leads the firm’s strategic advisory platform across four key practice areas: Client Advisory Services (CAS), Wealth Management, Technology & Risk Advisory, and Human Capital Advisory. Since joining Windes in 2013, Rob has been a driving force behind the firm’s transformation into a modern, tech-forward advisory powerhouse for closely held businesses and high net worth individuals.

With over 20 years of experience in tax strategy and financial consulting, Rob’s approach blends deep technical knowledge with practical, outcome-driven advisory. He is known for his ability to simplify complexity and deliver clarity, strategy, and results.

Advisory Leadership at Windes

Client Accounting Services (CAS)
Rob oversees a team of accounting and finance professionals who deliver outsourced controllership, accounting, and fractional CFO services. CAS empowers business leaders with timely, accurate financial insights and helps unlock capacity for growth and innovation.

Wealth Management
Through collaboration with internal advisors, Rob guides a team that supports clients with integrated planning strategies—helping align business and personal wealth objectives, including retirement, succession, and estate planning.

Technology & Risk Advisory
Rob leads professionals who assist clients with IT modernization, cybersecurity, risk management, and system integration. The focus is on helping businesses operate more efficiently, manage regulatory risk, and future-proof their operations.

Human Capital Advisory
Rob directs a growing practice that provides outsourced HR and recruiting solutions. The team supports clients in building scalable people operations, developing competitive compensation structures, and sourcing top-tier talent to drive organizational performance.

Exit Planning & M&A Advisory
As a Certified Exit Planning Advisor (CEPA) and Certified Mergers & Acquisitions Advisor (CM&AA), Rob also leads Windes' efforts in exit planning and M&A advisory. His team works with owners to increase enterprise value, reduce transaction risk, and structure successful transitions that minimize tax burdens and preserve legacy.

Known for his candid advice and strategic lens, Rob is a trusted resource to business owners navigating complexity and growth.

Outside the office, Rob enjoys golfing, and supporting his children’s athletic endeavors.