Learning Development Assistant Jobs in Winchester, MA

We are seeking a detailoriented and proactive Learning Management System (LMS) Administrator who embodies Odyssey's core values of Commitment, Ambition, and Respect. This role oversees the daily operation, optimization, and stewardship of our LMS-playing a key role in scheduling and coordinating learning initiatives, defining LMS pathways, and organizing highquality learning content.

The ideal candidate demonstrates Commitment through reliable system management and a dedication to enhancing the employee learning experience; Ambition through continuous improvement, technologydriven problemsolving, and innovative learning structure design; and Respect through clear communication, collaborative partnership, and userfocused support. This position is central to ensuring accurate reporting, compliance visibility, and a seamless learning ecosystem across Odyssey.

Duties include, but not limited to: 

LMS Administration & System Management

• Administer and maintain Learning Management System.
• Upload, assign, and track all courses. Including compliance, onboarding, and development content.
• Support course creation, updates, and user troubleshooting (access, course errors, navigation questions).
• Schedule, track, and support training initiatives for Learning & Development programs.
• Define LMS pathways and organize learning content by level, competencies, and role.
• Support updates or creation of courses in partnership with content owners.
• Develop and maintain LMS user guides for team members and managers.

Reporting, Data, and System Optimization

• Generate reporting on completions, overdue training, and compliance visibility for leaders.
• Maintain accurate training records to support compliance and audit requirements.
• Build and distribute dashboards, completion reports, and usage insights.
• Support data integrity and record accuracy in partnership with HRIS.
• Assist departments with understanding their compliance or training data.
• Participate in process improvements, automation, and system cleanup work for the LMS.

Onboarding & Employee Experience Support

• Ensure required onboarding content is properly assigned and available.
• Support orientation workflows and integration between HRIS and the LMS.

CrossFunctional Partnering

• Collaborate with functional content owners (Security, IT, HR, Finance, etc.) to deploy training and learning content.
• Provide guidance to leaders on how to use Odyssey University for developmental and required learning.

Citizenship: Must be a US citizen

Minimum Required Qualifications

• Bachelor's degree in Human Resources, Business Administration, or related field (or equivalent experience)
• 4-7 years of HR experience, with focus LMS administration, HRIS processing, and employee experience.
• Strong knowledge of HR systems and learning platforms (UKG and iCIMS a plus)
• Excellent organizational skills and high attention to detail
• Strong communication and customer service skills
• Excellent presentation and communication skills comfortable with all levels of employees and management
• Proficiency in Microsoft Office Suite and reporting tools

Preferred Qualifications

• Experience supporting system implementations or migrations
• Knowledge of data analytics and reporting tools
• Experience in a fast-paced or multi-location environment
• HR certification (e.g., SHRM-CP, PHR)

Core Competencies

• Process-oriented and systems-driven mindset
• Strong problem-solving abilities
• Ability to manage multiple priorities with accuracy
• Confidentiality and professionalism
• Collaborative team player

Location: Wakefield, MA

Hybrid, 3 days in office

#LI-MP1

Odyssey is a world-class technical, engineering, and integration company serving the warfighting ecosystem with airborne integration, ISR, C2, and warfighter readiness capabilities. Odyssey meets the military's operational needs by integrating layered defense systems from equipment, technology, and services to data, information, and business operations. We streamline defense acquisition and sustainment, engineering the technical battlefield with domain-specific proficiency to ensure lethality. Odyssey is dedicated to excellent contract execution, peak organizational performance, and fostering a workplace built on employee care.

Odyssey is proud to live out our core values of commitment, ambition, and respect in our work and communities through OdysseyCares, a philanthropic group focused on giving back through direct donations, an employer match program, and volunteering events.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities

Final compensation for this position will be determined by various factors such as the Federal Government contract labor categories and contract wage rates, relevant work experience, specific skills and competencies, geographic location, education, and certifications.

This position is filled through continuous recruitment and will remain open until a sufficient pool of applications has been received.Hired applicants may be eligible for benefits, including but not limited to, medical, dental, vision, life insurance, Tricare supplement, short-term disability, long-term disability, 401(k) match, flexible spending accounts, health savings accounts, employee assistance program, learning and development benefit, paid time off, and holidays.Odyssey Benefits