Planning and implementing online professional development opportunities is challenging but attainable. This paper explains how a group of librarians from different institutions worked to plan, market, implement, and evaluate monthly webinars as well as an inaugural online conference, despite never meeting in person. The web conferences began in-state and grew to include presenters and attendees from across the nation. A review of available web-conferencing technologies will be provided, including free and open-source options. This paper includes details about the planning process, including subcommittee collaborations, social media marketing, and day-of logistics. Failures during event planning and execution--and tips to avoid them--will be discussed, as well as next steps looking forward.