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Cover Letter

Richard OReilly
cheers@rorwashere.com
(203) 216-8796
Norwalk, CT
December 12, 2025
Dear Hiring Manager,

I'm writing to express my interest in a senior technology leadership position within your organization. With over fourteen years at Charitybuzz — where I currently serve as SVP of Technology—I've built a career on leading engineering teams that transform complex technical and product challenges into intuitive, scalable solutions.

At Charitybuzz I've guided a talented team across product engineering, IT, AI automation, and infrastructure, managing everything from software architecture and roadmapping to cross-functional collaboration between technology and business units. During my tenure, we've supported platforms like Prizeo and Chideo, raising over 1 billion for nonprofits and redefining how technology powers philanthropy, and even lead Charitybuzz.com through its acquisition.

One of my greatest strengths—and what I believe makes me a bit of a unicorn in this space—is my ability to bridge multiple disciplines with equal depth. I can design elegant user experiences, architect and build complex systems, and lead teams through both strategic and hands-on execution. Whether the need is creative direction, engineering rigor, or organizational leadership, I'm comfortable switching hats and ensuring that every layer of the process aligns toward the same goal: building technology that works beautifully and scales intelligently.

Beyond leadership, I remain deeply hands-on. My roots as a Fullstack Developer keep me grounded in technical excellence, allowing me to mentor effectively and ensure that strategic direction never loses touch with practical implementation. I believe the best leaders inspire trust through understanding every layer of the stack—from product ideation to system scaling.

I'm drawn to opportunities where I can apply this blend of vision, technical depth, and leadership to guide teams through growth, transformation, and innovation. I would love the chance to bring that experience to your organization and discuss how I can contribute to your goals. Thank you for your time and consideration. I look forward to the opportunity to connect.

Best regards,
Richard OReilly