
Strategic Transitions:
Driving District Growth with SWOT-KPI-SMART Integration
How Fennimore’s Administrative Team Translated Organizational Strengths into Measurable Student Outcomes for 2025–26.
Breakout Session
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Description
Streamlined transition process
The leadership team began with a comprehensive review of district-wide needs and then followed a structure planning process to create a Blueprint for Student Success for the upcoming school year. This blueprint includes:
Completing a SWOT analysis to assess the district’s current situation.
Identifying Key Performance Indicators (KPIs) aligned with student performance improvement.
Establishing SMART goals to guide growth and effectiveness through the SLO and Educator Effectiveness process.
PRESENTER: Jane Yeomans-Wonderling - District Administrator, Fennimore Community Schools
Jane Yeomans-Wonderling has served as the District Administrator for Fennimore Community Schools for the past nine years. Her career in public education spans 41 years, including 29 years as a classroom teacher and 12 years in administrative leadership. Under her direction, Fennimore Community Schools has experienced notable financial growth—most significantly increasing the district’s fund balance from 16% to 30% and establishing a $900,000 Fund 46 capital improvement reserve. In 2024, she partnered with the school board and a local advisory committee to lead the district through a successful $17 million capital referendum.
In addition to her work within the district, Jane serves as treasurer of the Southwest Wisconsin Technical College Board and is an active member of the Fennimore Economic Development Committee. For the 2025–26 school year, she is also participating in the AASA Advancing Rural Education Cohort, a national professional learning community focused on supporting rural school leaders. Jane remains a dedicated advocate for rural education and believes strongly in the power of community, family, and school partnerships.
PRESENTER: Hillary Day - Elementary Principal, Fennimore Community Schools
Hillary Day has been appointed as the Elementary Principal for the upcoming 2025–26 school year, bringing extensive experience and a strong commitment to rural education in Southwestern Wisconsin. For the past four years, she has served as the district-wide Assistant Principal for Fennimore Community Schools. Before returning to Fennimore, Hillary was the Elementary Principal and school counselor in Prairie du Chien, and earlier served as the school counselor at North Crawford, where she took on numerous administrative responsibilities. Additionally, she contributed at the state level through her four-year service on the Association of Wisconsin School Administrators (AWSA) Assistant Principals' Committee. Passionate about rural education, Hillary is dedicated to serving the students and families of Southwestern Wisconsin communities.