The Leadership Governing a New Standard
FOUNDER
EXECUTIVE CHAIRMAN
Managing
Director
OPERATIONS
COMMUNICATIONS
Henry "Hank" Dudgeon III, Founder and Executive Chairman of Legacy Technology Lab is an entrepreneur and investor known for scaling category-defining ventures. His superpower lies in translating bleeding-edge technologies into practical, scalable solutions for traditionally analog industries. As Founder of Legacy Technology Lab, he is advancing a data-driven approach to asset intelligence—reshaping how portfolios are evaluated, governed, and protected.
Hank’s work bridges technology, capital strategy, and operational execution, with strong ties to MIT’s innovation ecosystem. He also serves as Chairman of the Governing Dynamics Charitable Foundation, supports initiatives through JDP, and is Co-Founder of Davin Holdings, reflecting his commitment to long-term value creation and community impact.
Christopher Guarnera is CEO of Legacy Technology Lab, leading enterprise strategy, capital alignment, and national execution of its commercial roof intelligence platform. He oversees governance standards, operating frameworks, and the scalable deployment of Legacy’s objective, evidence-based methodologies across institutional portfolios. Chris directs standardized assessments and validation protocols that replace fragmented inspections with defensible infrastructure intelligence—supporting acquisitions, underwriting, capital planning, and long-term asset stewardship. A U.S. Army Reserve leader and certified UAV instructor, he brings disciplined execution and technical authority to scaling TRU Score standards nationwide for institutional owners and insurers.
Michelle Olenick is Managing Director at Legacy Technology Lab and a senior commercial real estate executive with more than 30 years of experience managing institutional office and industrial portfolios. Her background spans asset and property management, capital planning, construction oversight, and large-scale building repositioning initiatives.
Michelle has held leadership roles with premier firms including Hines, CBRE, and Cushman & Wakefield, where she managed institutional portfolios, directed multimillion-dollar capital projects, and partnered with ownership groups to execute strategic investment plans that enhance asset value and long-term performance. At Legacy, Michelle works closely with institutional owners and asset managers to support capital planning, reduce risk, and translate independent roof intelligence into practical, defensible decisions that protect portfolio performance.
Dustin Pendergrass is an operations and growth leader with a proven record of driving performance across multi-state roofing, construction, and infrastructure organizations. A U.S. Army combat veteran, he brings discipline, precision, and mission-focused execution to every initiative he leads. With more than 15 years of experience in business development and operations, Dustin specializes in scaling complex systems, streamlining processes, and aligning cross-functional teams to deliver measurable results. His expertise spans strategic sales, automation, and operational optimization supporting sustainable, scalable growth across enterprise platforms. Dustin is known for translating strategy into execution, strengthening partnerships, and ensuring high-performance outcomes.
Alicia VanderWal, brings a disciplined, mission-driven leadership background shaped by service in both the United States Army and law enforcement. She currently serves in the U.S. Army Reserves as a Senior Drill Sergeant, with prior roles in Air Defense Artillery, Military Police, and ceremonial units—leading, mentoring, and training personnel in high-accountability environments. A sworn police officer since 2013 and FAA-certified drone pilot, Alicia has supported aerial operations, real-time decision-making, and tactical coordination, while also serving as an instructor at multiple police academies. Alicia is recognized for building resilient teams, advancing responsible technology deployment, and leading with integrity, accountability, and purpose.
Susan Grossweiler is a marketing, communications, and operations executive with deep experience leading brand strategy and go-to-market execution for global technology and enterprise platforms. Her experience spans overseeing cross-functional divisions spanning application development, operations, and marketing driving SaaS growth initiatives and presenting alongside professional sports organizations on international stages. Her background includes senior leadership roles at Samsung Electronics, where she managed national retail accounts and complex B2B display programs, aligning supply chain, marketing, and sales operations across enterprise partners including The Home Depot, Lowe's, and ESPN Radio. Susan combines strategic messaging with operational rigor translating vision into executable, scalable outcomes that create impact.