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Jennifer Cunningham has a diverse work experience starting as a Training & Recruiting Coordinator at Daymon Worldwide in 2004. Jennifer then moved on to UBS Investment Bank where they worked as a Campus Recruiter and later as a Human Resources Manager. Following this, they interned at Operation Hope of Fairfield and CCA Inc. as a MSW Intern. Later, they held the role of Director, Program Management at LifeCare, before establishing Jennifer Cunningham Coaching in 2021 where they serve as a Transition & Leadership Coach, specializing in personal and professional potential optimization.

Jennifer Cunningham earned their Bachelor's degree in Psychology from Stonehill College in 2004. Jennifer then went on to complete their Masters in Social Work from Fordham University in 2012. In 2020, they obtained a Certified Professional Coach (CPC) and Energy Leadership Index Master Practitioner (ELI-MP) certification from iPEC Coaching. Additionally, in 2021, they obtained certifications as a COR.E Dynamics | Leadership Dynamics Specialist and COR.E Dynamics | Transitions Dynamics Specialist from iPEC Coaching. Recently, in 2022, Jennifer earned a certification as a Certified RETAIN Parental Leave Coach from the Center for Parental Leave Leadership.