The Wharton Women's Circles (WWC) at the University of Pennsylvania is a ground-breaking alumnae program founded in 2019 with a mandate to cultivate meaningful connections. The Circles, led by facilitators, provide working women a safe space to gather in an environment of support and encouragement. Through this process, women look to build community, confidence, inspiration, and produce desired results across personal and professional domains. Leveraging research in Positive Psychology, our team developed five facilitator-led sessions, encompassed in an adaptable ‘Playbook’ to support facilitators, engage participants, and drive discussions. The Playbook aims to accomplish three goals: (1) Amplify participant connection and well-being (2) Address survey feedback and the desire for more formal programming and structured conversations; and (3) Provide resources to enable future growth and scalability. The Playbook’s five facilitator-led sessions include: Know Your Strengths, Well-Being 101, Fostering Strong Relationships, Struggling Well, and Positive Transitions. We suggest measuring the Playbook’s efficacy through mixed qualitative and quantitative metrics.