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Tosa Gladys Two Heart, MBA has a diverse range of work experience spanning multiple industries. In their current role as the Community Behavioral Health Director at Great Plains Tribal Leader's Health Board, they are responsible for overseeing behavioral health initiatives. Prior to this, they worked as a CWOY Support Navigator at the same organization. Tosa has also held positions at Racing Magpie, where they worked as a Program Coordinator, and at Tosa Two Heart, where they served as the Chief Executive Officer. Ṫośa Gladys has experience in the art world, having worked as a Studio Artist at Racing Magpie and as a Fashion Show Committee Member at Native POP: People of the Plains. Additionally, Tosa has held roles in program management and collaboration at organizations such as First Peoples Fund and PWNA. Earlier in their career, they gained experience in customer service and admissions at Bentley University Graduate Admissions and took part in a summer fellowship at the Peabody Essex Museum. Prior to their MBA, Tosa served as the American Indian Recruitment Project Director at UCLA, where they oversaw operations and managed relationships with various entities and individuals.

Tosha Gladys Two Heart earned a Bachelor of Arts degree in Psychology from UCLA in 2012. In 2015, they pursued a Master of Business Administration (MBA) degree with a focus on Management/Leadership from Bentley University, which they completed in 2017. In 2019, they obtained the Native CDFI Practitioner Certification, specializing in Development Services, from the Neighborworks Training Institute. Additionally, in 2017, Tosha participated in the Regional Innovation in Germany Program organized by HHL - Leipzig Graduate School of Management.