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Jimmy O’Reilly

James “Jimmy” O’Reilly is the Head of Sales here at O’LYN Roofing and a Massachusetts native. He grew up in Newton, MA, known as “Little Hollywood” and the birthplace of the Fig Newton cookie, and currently lives in Needham, MA.

Jimmy brings a positive, curious mindset to work every day and believes that staying optimistic and collaborative makes the entire team stronger as they work toward shared goals. He joined O’LYN Roofing for its strong family culture and values, which he felt from his very first day.

Outside of work, Jimmy spends most of his time with his two kids and their activities, coaching many of their teams and proudly supporting them at every game. When he’s not with them, he enjoys golfing and following professional golf.

A fun fact about Jimmy: he played five years of professional golf, competed in both baseball and golf in college, and was an All-American in golf. He still coaches the game today because of his lifelong passion for it.

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Why Choose O’LYN Roofing?

Trusted Roofers Dedicated to Excellence Since 1974

With decades of experience, O’LYN Roofing has built a reputation for excellence in Greater Boston and MetroWest. You can expect:

  • Live phone answering and in-house customer support
  • Lifetime craftsmanship warranties for long-term confidence in our work
  • On-site project supervisors to ensure every detail is managed
  • Top credentials from Owens Corning Platinum Preferred, CertainTeed, and Velux
  • Full liability and workers' compensation insurance for peace of mind