About Bobby Bobby works with Orr Group’s nonprofit partners to strengthen operational systems through thoughtful technology implementation, automation, and responsible AI adoption. His work focuses on helping organizations reduce administrative burden, improve internal workflows, and build scalable systems that give staff more time and capacity to advance their missions. Bobby supports clients through assessment, training, and hands-on implementation of AI and automation tools tailored to each organization’s goals and operational realities. In addition to client work, Bobby leads Orr Group’s internal technology stack, ensuring tools are effectively implemented, maintained, and aligned with best practices. He trains Orr Group staff on practical and responsible uses of AI and automation, enabling the team to deliver innovative, efficient solutions to partners across sectors. Prior to joining Orr Group, Bobby spent a decade in nonprofit arts organizations, including the University of Maryland, College Park School of Theatre, Dance, and Performance Studies, and the Kennedy Center. In these roles, he managed complex operational systems for scheduling, budgeting, staffing, facilities, and technical training, and led cross-disciplinary teams of artists and administrators to deliver engaging, large-scale audience experiences. This background informs his collaborative, systems-oriented approach to helping nonprofit organizations build operations that are both sustainable and human-centered. Selected Recent Partners: Anthos|Home Blue Square Alliance Against Hate Heartshare Human Services of New York Youth INC What makes me happy is… Hosting a long board game night with friends, snuggling with my dogs Hero and Rebel, and learning something new each day. Favorite Book Genre Sci-Fi and Fantasy Recent Publications How to Drive Transformation with Strategic AI Implementation Don’t Just Use AI, Use It Right: Your Roadmap To Ethical AI Organizational Readiness 5 Cost And Time-Efficient Strategies For Nonprofits To Embrace AI AI In Grant Applications: Streamlining Or Skewing The Process?