About
CB Woodland is a strategic consulting and financial advisory firm focused on supporting established companies in complex decision-making environments. We work with organizations operating in capital-intensive and regulated sectors, providing clarity, structure, and confidence for critical strategic and financial decisions.
Our expertise includes strategic advisory, financial analysis, risk management, and governance support, with strong experience in structured investment and real estate-driven businesses. We partner with business leaders, investors, and institutions seeking disciplined growth, value protection, and long-term strategic alignment.
By combining analytical rigor with practical execution, CB Woodland helps organizations navigate expansion, restructuring, and capital allocation decisions with precision and accountability.
About CB Woodland
To deliver high-level strategic consulting and financial advisory services grounded in rigorous analysis, objective insight, and practical guidance for sound and sustainable decision-making.
Our Mission
To be recognized as a trusted strategic advisory firm for organizations and investors who value financial clarity, strong governance, and disciplined long-term growth.
Our Vision
Our Values
Strategic clarity
Transforming complexity into clear, actionable direction.
Sustainable growth
Strategies designed for resilience, continuity, and value preservation.
Integrity and accountability
Responsible advisory aligned with institutional standards and best practices.
Analytical rigor
Decisions supported by data, depth, and disciplined evaluation.
Trust-based partnerships
Relationships built on transparency, consistency, and delivery.
Senior real estate and venture capital executive with over 23 years of global experience in financial leadership, capital structuring, and strategic advisory.
He is currently Chief Financial Officer of Forest Development, a Palm Beach–based real estate development firm with $500+ million in active construction and a $2 billion development pipeline, and serves as Fractional CFO at Trioscope, Inc., a venture-backed technology and entertainment studio.
Chester has led capital structuring, investor relations, and strategic finance initiatives for real estate developers, institutional sponsors, and family offices across the United States, Middle East, and Europe. He began his career at Booz Allen Hamilton and spent over a decade in Dubai, advising clients on large-scale developments, acquisitions, hotel transactions, and financial restructurings.
He holds an MBA from the University of Chicago Booth School of Business, an MPA from Harvard University, a Master of Legal Studies from UCLA, and a BA in Economics from the University of Virginia. He is a CFA charterholder, formerly held FINRA Series 7 and 63 licenses, and is fluent in German, Spanish, and French, with conversational proficiency in Italian and Portuguese.