Wisewrds is a web application to facilitate part-time bridge employment through mentorship to retired and/or retirement-eligible faculty members in the academic sector. Through a user-centered design approach, the project examines the potential challenges and opportunities afforded by inter-age knowledge transfer for faculty members and students. The online platform is built in response to support post-retirement employment through informal mentorship in a flexible working environment. Wisewrds is at the intersection of faculty interested in encore career, emerging scholars seeking mentorship and organizations concerned about institutional memory loss. This research project opens up a dialogue to respect the transitional steps of retirement to support the experience of post-retirement age.