Summary
Overview
Work History
Education
Skills
Languages
Timeline
Generic

Skye Flanagan

Baker City,OR

Summary

Dynamic school administrator with over a decade of leadership experience across elementary, middle, and high school settings, including five years leading comprehensive high school improvement as Principal of Baker High School. Proven success in rebuilding school culture, designing cohesive systems, providing targeted professional development for staff, and expanding access to advanced, dual credit, & college-level learning opportunities. Collaborative, student-centered leader committed to equity, innovation, and preparing students for successful postsecondary transitions.

Overview

24
24
years of professional experience

Work History

High School Principal

Baker School District 5J
Baker City, OR
07.2021 - Current

Led comprehensive school improvement efforts focused on culture, systems, and postsecondary readiness in a rural high school setting serving diverse learners.

  • Rebuilt school culture through intentional relationship-building, shared leadership structures, and clear systems of accountability and support.
  • Designed and implemented cohesive academic and behavioral systems that increased graduation rates above the state average and improved daily attendance.
  • Expanded access to advanced coursework, online learning, and dual credit opportunities to ensure students could accelerate learning based on readiness and goals.
  • Strengthened and sustained postsecondary partnerships with Blue Mountain Community College and Eastern Oregon University, ensuring aligned, credit-bearing opportunities for all students.
  • Strategically leveraged Measure 98 funding to develop and refine a Freshman On Track Team, improving ninth-grade transitions and long-term student success.
  • Provided targeted professional development focused on high-quality instruction, assessment literacy, and standards alignment.
  • Managed and strategically allocated a $340,000 discretionary budget to support instructional priorities, school operations, and student achievement.
  • Collaborated closely with middle school administrators and staff to vertically align systems and instructional practices across grades 7–12.
  • Worked with regional online charter schools to develop hybrid and alternative learning systems responsive to student needs.

Middle School Principal

Baker School District 5J
Baker City, OR
07.2017 - 06.2021
  • Led schoolwide improvement initiatives grounded in data-informed decision-making and collaborative leadership.
  • Built systems to improve student engagement, academic performance, and staff effectiveness.
  • Fostered a positive, inclusive school culture centered on strong relationships with students, staff, and families.
  • Guided staff and community through COVID-19 disruptions while maintaining high expectations and implementing innovative instructional practices.
  • Strengthened communication and collaboration between school and community stakeholders.

Elementary School Principal

Baker School District 5J
Haines, OR
07.2015 - 06.2017
  • Led a rural PK–6 school with a focus on culture, instructional quality, and organizational growth.
  • Developed foundational skills in budgeting, curriculum leadership, and professional development.
  • Implemented initiatives that increased student engagement, staff collaboration, and school pride.
  • Built strong partnerships with families and community members to support student learning.

Social Studies Teacher

North Powder School District
North Powder, OR
08.2012 - 06.2015
  • Developed a curriculum that focused on the delivery of World Geography through a historical context.
  • Facilitated classroom discussions to promote critical thinking and foster a collaborative learning environment.
  • Developed a positive classroom environment by fostering open communication, respect, and collaboration among students.
  • Implemented project-based learning activities that encouraged students to apply their knowledge to real-life situations, enhancing problem-solving skills and deepening understanding of course concepts.

4th Grade Teacher

North Powder School District
North Powder, OR
08.2004 - 06.2015
  • Developed engaging lesson plans aligned with state standards to enhance student learning and participation.
  • Fostered a positive classroom environment that encouraged student collaboration and respect.
  • Integrated technology and multimedia tools into lessons to enhance student learning.
  • Worked directly with colleagues to develop systems around PBIS, RTI, and student engagement.

6th Grade Teacher

Culver School District
Culver, OR
08.2002 - 06.2004
  • Developed engaging lesson plans aligned with curriculum standards.
  • Fostered a positive classroom environment to enhance student learning experiences.
  • Actively participated in school-wide committees focused on improving overall campus culture, fostering collaboration between educators for enhanced student experiences.

Education

Administrator License - School Administration

Concordia University - Chicago
Chicago
2015

Master of Arts - Education

Eastern Oregon University
La Grande, OR
2001

Bachelor of Arts - International Relations/Educational Studies

Carleton College
Northfield, MN
1998

Skills

  • Instructional Leadership
  • Student Engagement
  • Staff Development
  • Organizational Management
  • Process Improvements
  • Relationship Building

Languages

German
Limited Working

Timeline

High School Principal

Baker School District 5J
07.2021 - Current

Middle School Principal

Baker School District 5J
07.2017 - 06.2021

Elementary School Principal

Baker School District 5J
07.2015 - 06.2017

Social Studies Teacher

North Powder School District
08.2012 - 06.2015

4th Grade Teacher

North Powder School District
08.2004 - 06.2015

6th Grade Teacher

Culver School District
08.2002 - 06.2004

Administrator License - School Administration

Concordia University - Chicago

Master of Arts - Education

Eastern Oregon University

Bachelor of Arts - International Relations/Educational Studies

Carleton College