| Sumario: | Background: Aligning undergraduate and early postgraduate clinical training remains challenging. We evaluated a tiered competency checklist ("Step Ladder System") implemented in an obstetrics–gynecology (OBGYN) rotation using a mobile assessment platform. Methods: We retrospectively analyzed 74 learners (41 final‐year medical students, 33 first‐year residents) who completed an OBGYN rotation at a Japanese university hospital (April 2022–November 2024). The Step Ladder System includes 93 workplace‐based tasks across obstetrics, gynecology, and general practice, organized into three progressive steps (Steps 1–3). Outcomes were stepwise completion rates, gender differences, supervisor ratings, and app‐recorded feedback. We also identified "seamless" tasks and "low‐achievement" tasks to inform curriculum improvement. Results: Students achieved higher completion than residents in Step 1 (82.4% vs. 73.2%, p < 0.05), similar completion in Step 2 (59.2% vs. 54.4%, ns), and lower completion in Step 3 (17.1% vs. 22.1%, p < 0.05). Female learners showed higher completion in several knowledge‐focused Step 2 tasks, while a small number of procedural tasks favored males. Supervisor ratings were predominantly positive (4–5/5), supported by encouraging narrative comments. Ten "seamless" tasks (high completion in both groups with minimal between‐group differences) indicated similar achievement patterns across learner groups, whereas "low‐achievement" tasks (low completion across learners) clustered in advanced Step 3. Conclusions: A mobile, stepwise competency checklist provides a structured framework for clinical training and enables real time documentation and feedback. Completion data may serve as a curriculum diagnostic tool by highlighting stable competencies and potential gaps.
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