For more than two decades, Omar Messado has navigated the complex world of transportation procurement, infrastructure contracts, and rolling stock acquisitions across New York’s transit agencies. His definition of success, however, has little to do with the numbers on a balance sheet.
Every morning before the workday begins, Omar Messado slips into a pool and swims. He started this habit at 50, an age when many people settle into established routines rather than build new ones. For him, the water offers something more functional than fitness. It clears his mind. It creates what he describes as a clean slate, a necessary reset for someone whose career has been spent managing the friction points between public agencies, private vendors, and multimillion-dollar procurement cycles.
Messado has spent over 20 years in transportation procurement, moving through the ranks of New York’s Metropolitan Transportation Authority and its subsidiaries. He has overseen contracts for rolling stock, negotiated design-build agreements, and directed procurement operations across infrastructure projects that keep millions of commuters moving. His roles have included Senior Director of Metro-North Railroad Procurement, Assistant Deputy Chief Procurement Officer at the MTA, and Manager of Contract Administration at Kawasaki Rail Car, Inc. The work is technical, often invisible to the public, and deeply consequential.
The Immigrant Path Through New York’s Schools and Agencies
Born in Jamaica, Messado immigrated to the United States by age 10. He grew up in New York City with two brothers. His father worked as an electrical engineer for Con Edison. His mother held a secretarial position at a corporate office in the city. The family moved between Brooklyn, the Bronx, and other parts of New York, and Messado attended parochial schools in each neighborhood. He graduated from Rice High School in 1986 and went on to earn a BBA in Finance from Iona College in 1990. Later, he pursued coursework in Financial Planning at Pace University and completed a Master of Science in Civil Engineering and Transportation Management from what is now the NYU Tandon School of Engineering in 2012.
His career began in 1998 as an Associate Staff Analyst at MTA New York City Transit. Over the next decade, he moved through roles in quality control, transit management analysis, and procurement. In 2005, he joined Kawasaki Rail Car, Inc. as Manager of Contract Administration and Marketing, a position that placed him on the vendor side of the contracts he once managed. By 2009, he returned to the MTA system as Manager of Procurement and Material Management at Metro-North Railroad. He climbed steadily from there, becoming Assistant Director in 2014, Senior Director in 2017, and Assistant Deputy Chief Procurement Officer in 2023. He left the MTA in October 2025 and now works remotely as a Procurement Specialist.
A Leadership Philosophy Built on Team Success
Messado states that his success is measured not by personal milestones but by the accomplishments of those he has managed, guided, or supported. He describes success as the moment when a team member completes a project, exceeds expectations, or moves into a role they were once unready for. He frames leadership as a responsibility to create space for others to grow, even when that growth means learning from mistakes.
He credits much of his approach to a mentor named Gennaro Sansone, known as Gene, who shaped his understanding of what it means to lead without ego. Messado states that a leader should be open to learning from those he supervises, give credit where it is due, and understand that errors are inevitable. The goal, he says, is not to avoid mistakes but to ensure they are not repeated.
This philosophy has guided his work across procurement cycles that involve coordination between engineering teams, legal departments, executive leadership, and external contractors. He has led negotiations for rolling stock acquisitions, infrastructure upgrades, and design-build contracts. He has also directed teams tasked with meeting key performance indicators under tight deadlines and shifting regulatory environments. His approach emphasizes clarity, accountability, and the development of future leaders within the procurement function.
Tools, Certifications, and the Mechanics of Procurement
Messado has worked extensively with SAP Material and Procurement Management Systems, PeopleSoft Oracle Database E-Procurement platforms, and a range of Microsoft Office and Adobe PDF applications. He holds advanced certifications in Risk Assessment, Budgets and Cost and Price Analysis, Situational Leadership and Decision Making, Managerial Critical Thinking, Business Writing, Political Savvy, and the Fundamentals of Design Build Project Delivery. These credentials reflect the breadth of skills required in a field where contract language, financial modeling, and interpersonal negotiation intersect.
He is a member of the American Public Transportation Association and the National Institute of Governmental Purchasing. Outside of work, he is involved with the Yonkers Bike Club and Westchester Social Cyclists, both of which align with his interest in cycling. He also volunteers with the Ossining Food Bank and Pantry and has supported the Boy Scouts of America.
Values, Routine, and the Long View
Messado states that not everyone will appreciate your qualities, and that values should not be surrendered for approval. He advises setting specific short-term and long-term goals, prioritizing them based on complexity and available resources, and identifying the next step in a career as soon as the current role becomes clear. He describes this as a form of succession planning applied to one’s own trajectory.
When faced with self-doubt, he returns to the pool. The morning swim, begun in his 50s, has become a ritual of mental preparation. It is not about achievement or performance. It is about clearing space for the day ahead.
Omar Messado and the Work That Remains
Messado now works remotely, applying the same procurement expertise that once navigated the bureaucratic and technical demands of the MTA to new contexts. He continues to advocate for mentorship, personal accountability, and leadership development. He states that the most meaningful professional moments are not promotions or completed contracts, but the paths taken by people he helped along the way. His career, built across transit agencies, vendor relationships, and infrastructure projects, reflects a belief that the work of leadership is not to be seen, but to make others visible.
He remains based in Ossining, New York, where he lives and continues to swim most mornings. The pool is quiet. The work, as always, is just beginning.
