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Experience

Simon Ostrander is an accomplished executive leader with extensive experience in strategic leadership, organizational development, and ethical decision-making across both civilian and military sectors. Currently pursuing a Doctorate in Executive Leadership, he specializes in navigating complex environments through systems thinking, relationship-building, and leadership through standards. Simon’s career reflects a commitment to servant leadership, professional excellence, and fostering growth in others. His work is guided by the LEVVI leadership model, which integrates ethical principles, adaptive strategies, and continuous development to drive meaningful, long-term impact.

View below for his professional resume.

Professional Resume

Professional Experience

Training and Education Senior Advisor

2024 - Present

  • Lead a team of 30 staff and contractors in the training and education group, ensuring programs meet Senior leadership performance standards.

  • Oversee the delivery of standardized training to more than 600 personnel annually, ensuring consistency and quality across all iterations. 

  • Supervises the proper exploitation and exploration of dynamic capabilities within the training and education group to ensure lethality and warfighting are the priority.

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Strategic Field Operations Lead​

2022 - 2024

  • Directed a high-performing, cross-functional team in remote and resource-limited environments, meeting critical organizational objectives under tight timelines.

  • Planned and executed complex field operations that closed key information gaps, directly supporting high-level decision-making.​​

  • Coordinated logistics, risk assessments, and stakeholder communications to ensure mission success in challenging and dynamic conditions.

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Director Of Operations

2018 - 2022

  • Oversaw daily operations for a high-performance team, ensuring alignment with organizational priorities and executive-level expectations.

  • Managed planning, coordination, and execution of complex projects in dynamic, high-pressure environments.

  • Directed cross-functional collaboration, resource allocation, and process improvement initiatives to optimize performance.

  • Project lead for the training and assessment of over 600 candidates in an introductory level coursework.

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Section Leader

2015 - 2018

  • Coordinated tasks, resources, and timelines to achieve high-priority objectives under challenging conditions.

  • Served as the primary liaison between team members and senior leadership, ensuring effective communication and alignment.

  • Trained, mentored, and evaluated team members to maintain peak performance and operational readiness.

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Education

2023 - Present

University of Charleston, West Virginia

Doctor of Executive Leadership

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2020 - 2022

University of Charleston, West Virginia

Master of Science in Strategic Leadership with Honors

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2018 - 2020

University of Charleston, West Virginia

Bachelor of Science in Organizational Leadership 

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Awards and Recognition 

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Double recipient of the Military Purple Heart​ 

Recipient of the Joint Meritorious Service Medal

Triple recipient of the Navy and Marine Corps Accommodation Medal, to include one for "Valor" and "Combat"

Double Recipient of the Navy and Marine Corps Achievement Medal, to include one for "Valor"

Recipient of the Outstanding Volunteer Service Medal

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Affiliations

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2014 - Present

Military Order of the Purple Heart, Jacksonville, NC 

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Volunteer Work

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2022 - Present

Onslow County and Surf City, Recreation Youth Volleyball Coach

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2020 - Present

Architectural Review Committee Member/Chair for Home Owner Association 

Contact

I'm always looking for new and exciting opportunities. Let's connect.

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