We describe a training series using a scaffolded approach informed by Vygotsky’s Learning Theory to advance Hawai‘i -based faculty grant-writing skills. Sponsored by the Professional Development Core of the Center for Pacific Innovations, Knowledge, and Opportunities (PIKO) at the University of Hawai‘i at Mānoa, the initiative includes a 2-week series of 1-hour introductory sessions on aspects of grant writing, a 3-session workshop to develop a specific aims page, and a 5-month training program in grant writing. Over three years, 202 Hawai‘i investigators attended at least one 1-hour introductory session, 62 completed the workshop on preparing specific aims, and 30 completed the 5-month training on grant writing. Participants rated all 3 programs as very useful. Of the 62 unique investigators who completed the Specific Aims Workshop, 21 (33%) submitted PIKO pilot grant applications, 4 (6%) submitted grants elsewhere, and 16 (30%) applied to the 5-month training on grant writing. The 30 GUMSHOE participants reported significant gains in their confidence in accomplishing 21 proposal-writing tasks and, as of May 2025, 26 (87%) submitted grants to the National Institutes of Health or another external funder. This scaffolded training approach is labor- and time-intensive for trainees and faculty mentors, but our outcomes demonstrate its success.