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Kevin Boland has a diverse work experience spanning various industries and roles. Starting from 2006, they worked as the Director of Quality Assurance & Technology at SaintA, where they supervised staff and ensured compliance with regulations. In 2008, they held roles such as Implementation Consultant at T2 Systems, Change Coordinator at Fujitsu, and Manager of Volunteer Services at Odyssey Health Care. From 2009 to 2010, they served as the Ongoing Services Supervisor at Children's Hospital of Wisconsin - Community Services. Boland also worked as an Adjunct Instructor at Bryant & Stratton College from 2008 to 2016. Additionally, they have previous experience in program evaluation, quality improvement, and management roles at the Division of Milwaukee Child Protective Services - Department of Children & Families. Presently, they are the Vice President of Programs and Services at Jewish Family Services. Kevin is also an Adjunct Lecturer at the University of Wisconsin-Milwaukee.

Kevin Boland earned a Bachelor of Science (B.S.) degree in Sociology and Psychology from Longwood University in the years 1990 to 1994. Kevin later pursued a Master of Arts (M.A.) degree in Sociology from the University of Wisconsin-Milwaukee from 1995 to 1999. In 2014 to 2015, Kevin obtained a Master of Education (M.Ed.) degree in Curriculum and Instruction & Career and Technical Leadership from Concordia University-Portland. Kevin also holds additional certifications such as Trainer from Crisis Prevention Institute (obtained in August 2013), Certified Social Worker from the State of Wisconsin - Social Work Section (obtained in June 2010), and Project Management from the University of Wisconsin - Madison (obtained at an unspecified date in 2010).