Summary
Work History
Education
Skills
Timeline
Generic

CAITLIN O'SHEA

Seattle,WA

Summary

Transformational systems and operations leader with expertise in managing multimillion-dollar portfolios and driving organizational change across diverse sectors. Skilled in leading large teams, advising executive leadership, and enhancing compliance and accountability. Proficient in navigating complex stakeholder environments, translating data into actionable strategies, and resolving operational challenges to improve efficiency, quality, and service delivery.

Work History

Progressive Leadership Student Support Supervisor

SEATTLE PUBLIC SCHOOLS
Seattle, WA
2018 - 2026
  • Promoted through three progressively responsible roles, advancing from program expertise to regional leadership and districtwide oversight of complex student support systems, personnel, contracts, compliance, policy, and organizational initiatives.
  • Managed a $10M portfolio, 100+ external contractors, and performance evaluation for 100+ staff across complex service systems.
  • Redesigned behavioral support systems, reducing one-to-one behavioral staffing by 71% and enhancing system efficiency.
  • Conducted internal audits of transportation and external contracts, redesigning processes to achieve $1M+ in cost savings.
  • Maintained a 98% regulatory compliance rate with federal Individuals with Disabilities Education Act (IDEA) requirements across complex operational and program activities.
  • Designed districtwide policies and redesigned programs that contributed to an 83% improvement in positive client outcome metrics.
  • Advised executive leadership and partnered directly with attorneys on litigation, compliance, risk, policy, and high-stakes organizational matters.
  • Guided managers and specialists in service improvement, organizational change, conflict resolution, and crisis management.
  • Designed and supported 100+ professional development offerings, achieving 95% staff satisfaction.
  • Evaluated system performance and translated quantitative and qualitative findings into operational recommendations, policy changes, and program improvements.

Consulting Engagements

RESEARCH, CONSULTING & ORGANIZATIONAL IMPROVEMENT
2009 - 2018
  • Identified and engaged with key organizations, including RAND Corporation, Center on Reinventing Public Education, College Success Foundation, and TNTP, to foster collaboration.
  • Advised executive leaders and organizations on enhancing organizational performance, systems effectiveness, and strategic improvement initiatives.
  • Evaluated organizational performance and system effectiveness across complex initiatives, integrating qualitative and quantitative analysis to identify opportunities for improvement.
  • Partnered with executive and organizational leaders to diagnose operational challenges, develop strategic recommendations, and support implementation.
  • Guided 12+ public-sector and nonprofit organizations in navigating complex institutional and operational challenges, transforming stakeholder input into actionable improvement plans.
  • Translated research, stakeholder input, and performance data into actionable recommendations for organizational strategy, policy, and program design.
  • Developed and published 50+ policy recommendations across multiple initiatives and sectors.

Special Education Teacher

OAKLAND UNIFIED SCHOOL DISTRICT
Oakland, CA
2008 - 2013
  • Facilitated student achievement, resulting in 95% of participating students advancing two grade levels on benchmark assessments.
  • Founded pilot inclusion program serving 150+ students, collaborating with students, families, educators, and stakeholders to develop a new service model.
  • Developed IEP goals for Oakland Unified School District students with diverse learning needs.
  • Delivered specialized instruction aligned with state standards and district curriculum.
  • Collaborated with general education teachers on classroom accommodations and modifications.

Co-Founder and Program Director

THE DREAM PROJECT
, Dominican Republic
2003 - 2009
  • Co-founded and scaled an international youth development organization from inception into a multi-program organization with 50 staff and 300 volunteers.
  • Managed global team of 54 counselors, overseeing recruitment, coaching, performance assessment, and professional development to enhance team effectiveness.
  • Created and launched nine sustainable community programs addressing education, youth development, and community needs.
  • Founded a vocational initiative serving 1,500+ adolescents, developing partnerships and program structures to support scale and sustainability.
  • Established hiring, staff development, program evaluation, and operational processes, enabling scalable growth and sustainability of the organization.

Other Professional Experience

TYCO
Other Professional Experience
  • Processed financial transactions and reconciled accounts to ensure accuracy and compliance.

SMITH, MCCARTNEY & OWEN LAW FIRM
  • Legal operations and client services

RETAIL & HOSPITALITY
  • Customer service and operations

Education

WA Resident Program Administrator Program Certification (ECSEL) - Bothell, WA

UNIVERSITY OF WASHINGTON
Bothell, WA
01-2022

Master's - Educational Policy

UNIVERSITY OF WASHINGTON
Seattle, WA
01-2015

Bachelor of Science - Biopsychology and English

CORNELL UNIVERSITY
Ithaca, NY
01-2005

Skills

Systems Leadership Organizational Transformation Strategic Planning Systems Design Program Evaluation Operations Management Organizational Change Budget and Resource Management Compliance and Accountability Regulatory Compliance Performance Management Policy Development Executive Advising Team Leadership Cross-Functional Collaboration Conflict and Crisis Management Community Partnerships Stakeholder Engagement

Timeline

Progressive Leadership Student Support Supervisor

SEATTLE PUBLIC SCHOOLS
2018 - 2026

Consulting Engagements

RESEARCH, CONSULTING & ORGANIZATIONAL IMPROVEMENT
2009 - 2018

Special Education Teacher

OAKLAND UNIFIED SCHOOL DISTRICT
2008 - 2013

Co-Founder and Program Director

THE DREAM PROJECT
2003 - 2009

Other Professional Experience

TYCO
Other Professional Experience

SMITH, MCCARTNEY & OWEN LAW FIRM

RETAIL & HOSPITALITY

WA Resident Program Administrator Program Certification (ECSEL) - Bothell, WA

UNIVERSITY OF WASHINGTON

Master's - Educational Policy

UNIVERSITY OF WASHINGTON

Bachelor of Science - Biopsychology and English

CORNELL UNIVERSITY
CAITLIN O'SHEA