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Jessica Hill has a diverse work experience spanning over several industries. Jessica began their career at Kaplan Professional as a Client Services Representative in 2006 and later worked as a Logistics Assistant at Kaplan Higher Education from 2009 to 2010. Jessica then joined Saint Ignatius College Prep as a Counseling Department Intern from 2010 to 2011. Jessica continued their career as an Undergraduate Admissions Applications at Northwestern University for a brief period in 2012.

In the same year, they joined Kaplan University as an Education Advisor and later became a Student Life Specialist from 2014 to 2014. Concurrently, they were also working as a Nanny at North Shore Nannies from 2012 to 2019.

In 2015, Jessica joined Everspring and progressed through various roles, including Manager of Student Services from 2017 to 2019, Director of Student Services for a brief period in 2019, Executive Director of Student Services from 2019 to 2023, and currently serves as the Vice President of Student Services.

Overall, Jessica Hill has built a strong background in student services and has gained experience in client services, admissions, counseling, and education advising throughout their career.

Jessica Hill completed their Master's degree in Education, specializing in School Counseling, from DePaul University in the years 2009 to 2011. Jessica then pursued a Graduate Certificate in Educational Leadership K-12 from Kaplan University from 2013 to 2014. Prior to that, they obtained their Bachelor's degree in Sociology, with a focus on Social Welfare and Social Services, from the University of Michigan, where they studied from 2002 to 2006. In addition, Jessica has obtained various certifications in fields such as mindfulness, diversity, inclusion, belonging, and unconscious bias from LinkedIn. Jessica has also received a Type 73 School Service Personnel Certificate, though the institution and year of completion are not specified.