Demo

Learning Technologies Specialist, Sr

Chubb Benefits
Chicago, IL Full Time
POSTED ON 4/28/2026
AVAILABLE BEFORE 5/27/2026

Chubb Benefits is seeking a Senior Learning Technologies Specialist to join our fast-paced, high energy, growing company. We are proud of our tradition of success in the insurance industry of over 100 years. Come join our team of hard-working, talented professionals!


Job Summary

The Senior Learning Technologies Specialist is a dynamic role, accountable for managing the development, deployment, and adoption of creative and innovative online and blended learning programs and experiences. Candidate will serve as LMS Administrator for multiple internal audiences across several platforms and will also be an integral member of our Instructional Design team.


All candidates must have technical expertise related to learning technologies (eLearning development tools, LMS administration, virtual training platforms) to implement, track, and market learning programs. In addition, solid project, time, and relationship management skills are essential, as well as the ability to work independently, prioritize, troubleshoot, and take ownership. Detail-oriented candidate should be curious and strategic when it comes to utilizing learning technologies and interacting with internal clients, vendors, and partners within a matrixed organization. The desire and ability to quickly learn and navigate through complex business processes and systems to accomplish goals is critical.

Responsibilities

  • Serve as primary LMS Administrator, owning governance and change management processes, maintaining online course, video, and test content library, and maintaining organization of in-person and virtual instructor-led session setup.
  • Serve as a partner to the business, collaborating across multiple initiatives to create blended learning programs and curriculums to be deployed and managed via the LMS.
  • Serve as content/program owner for blended learning programs deployed in the LMS: add new content, update or retire outdated materials, analyze usage and adoption, ensure assignments are processed and tracked (right content-right audience-right time).
  • Work with IT departments to execute and maintain various LMS integrations.
  • Collaborate with Learning Delivery and Field Development teams to conduct functional and user-acceptance testing, recommend new approaches, implement, and ensure business users are enabled to execute ongoing administrative (Train-the-trainer, job aids, admin manuals).
  • Evaluate automated processes versus manual processes when creating new programs, balancing the needs of clients and projects with various system capabilities.
  • Interact with LMS support vendor to execute testing of learning items to ensure quality of deployed learning materials.
  • Interact with translation vendors to ensure content is available in required languages.
  • Analyze and communicate the metrics of learning effectiveness; run reports out of the LMS and analyze using advanced Excel skills to provide feedback and recommendations to management for ongoing improvement.
  • Leverage decision-making skills, critical thinking, and reasoning. Proactively resolve problems while exhibiting professional, sound judgment and leadership skills.
  • Troubleshoot known issues and respond to user issues and stakeholder questions to ensure a positive LMS admin and end-user experience. Escalate to vendor when needed. Provide excellent and timely customer service to maintain the positive reputation of our department and platforms.
  • Keep a pulse on strategic objectives while maintaining knowledge of features and tools in the LMS to recommend new approaches; maintain awareness around features that are retiring and impact to business processes (proactive, not reactive).
  • Support our Claims and Operations training team and end-users across multiple LMS systems.

Competencies, Specific Skills

  • Learning Management Systems administration, support and troubleshooting experience (experience with Cornerstone is a plus).
  • Ability to test eLearning content within an LMS, and troubleshoot and correct issues with the content, to maintain usability and reliability within the LMS.
  • Superior writing, communication, and presentation skills; ability to state issues in a concise, solution-driven manner.
  • Outstanding organizational skills, attention to detail, project management skills and proficiency in prioritizing/reprioritizing tasks based on changing needs.
  • Ability to work under deadlines balancing multiple priorities, complete tasks to agreed time and quality standards.
  • Ability to quickly establish strong working relationships with all levels of personnel across multiple departments.
  • Ability to organize workflow to manage multiple projects and accomplish tasks with follow-through to completion.
  • Strong Reporting and Excel skills – vlookups, conditional formatting, pivot tables
  • Experience working with IT departments and working on technology projects.
  • Strong analytical and problem-solving capability, with an orientation towards continuous process improvement.
  • Experience with virtual roleplay tools, virtual delivery tools such as Webex, machine audio narration tools, micro-learning platforms, LCMS, video editing software, SharePoint/Teams.
  • Experience troubleshooting end-user issues via ticketing system or shared mailbox; experience with handling escalations and advanced troubleshooting.
  • Current knowledge of the latest training technologies and training program design strategies.
  • Some light Instructional Design work required, as assigned.
  • Ability to follow designated approval processes for content review, including SME and Legal review.
  • Some LMS-focused live facilitation (i.e. Train-the-trainer) required.
  • Some travel may be required, up to 25%.


Education and Skills

  • BS/BA degree (or equivalent experience/certifications) in Instructional Design, Instructional Technology, Training and Development or related field preferred.
  • Master’s degree in Instructional Design is preferred.


Preferred Experience

  • Bilingual in Spanish a plus.
  • Adult learning strategies, including online learning and rapid design principles.
  • 2 years using Learning Management Systems. Experience with Cornerstone OnDemand LMS a plus.
  • Instructional Design experience: conduct needs analysis, create PowerPoint presentations for live and virtual training, using eLearning software, and writing job aids/user manuals.
  • Demonstrated ability to design learning solutions for eLearning and live virtual instructor-led experiences.
  • Ability to analyze information quickly, develop curriculum outlines and draft training content.
  • Articulate Storyline, Articulate Rise required.
  • Camtasia, Captivate, Photoshop, Canva, and Adobe Illustrator a plus.
  • WebEx and/or Adobe Connect to deliver virtual programs
  • Proficiency in Microsoft Office products, including Excel, Word, Outlook, Project, and PowerPoint.
  • Report development and analysis experience (Excel, PBI, etc.).
  • Project and vendor management.
  • Working in B2B, Group and Broker insurance a plus.
  • Insurance, Sales, Operations, Call Center, or Insurance Claims Departments a plus.


The pay range for the role is $80,000 to $120,000. The specific offer will depend on an applicant’s skills and other factors. This role may also be eligible to participate in a discretionary annual incentive program. Chubb offers a comprehensive benefits package, more details on which can be found on our careers website. The disclosed pay range estimate may be adjusted for the applicable geographic differential for the location in which the position is filled.

Salary : $80,000 - $120,000

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