A lifelong Hawai’i resident, Maile’s first career was as a teacher. While she still enjoyed teaching, she left the Department of Education after ten years to pursue her passion for event management. She honed her craft for five years while planning significant events for non-profits in Hawai’i, Texas, Missouri, Kansas, Oklahoma, Nebraska, and Guam. Destination management in Hawai’i was the next logical step, and she spent over six years with Panache before taking her focus and skill set to Weil & Associates, which is now PRA Hawai’i.