If you are a grants or research administrator working at a small predominantly undergraduate institution, have you ever wondered where you stand in relation to other similar institutions? Have you thought about what you need to do to get yourself, your office, and your institution to the "next level" of outreach to or support for the faculty? Have you asked what are reasonable benchmarks or milestones to which you can aspire in leading your office? In this article the authors focus on two parallel cycles of development within a small grants office at a predominantly or primarily undergraduate institution (PUI). One cycle is the development of the office itself as it is shaped by the institution, faculty research activity, and intramural and extramural funding priorities. The second cycle is the development of the research administrator as the professional grows and matures. The authors will walk the reader through the phases of development as they are influenced by challenges and milestones characteristic of successful research development.