Employee Benefits Systems Trainer - Remote

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Must be eligible to work in the United States without the need for work visa or residency sponsorship.
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Our Newest Opportunity:
Summary:
The Dynamics 365 & Employee Benefits Systems Training Specialist partners with Product Development teams, Employee Benefits (EB) and Human Resources Consulting (HRC) Subject Matter Experts (SMEs), and business stakeholders to identify learning needs and design training solutions that drive employee proficiency and adoption of Microsoft Dynamics 365. The role translates system functionality and business processes into practical, engaging learning experiences that enable employees to successfully perform their roles.
This position is the primary learning lead for Dynamics 365 across the Employee Benefits and HRC practices, responsible for programs that support new hires, existing employees, acquired teams, and ongoing system enhancements.
This role also serves as a connector across the Employee Benefits technology ecosystem, helping employees understand how Dynamics 365 integrates with Outreach, ZoomInfo, and other connected technologies that support business workflows.
The ideal candidate combines Employee Benefits business knowledge, technical systems expertise, facilitation excellence, instructional design capability, and strong relationship-building skills.
Essential Duties and Responsibilities
Design and Develop Training Programs
Create and deliver training programs for Microsoft Dynamics 365 and related Employee Benefits technology solutions
Develop role-based learning paths aligned to producer, account management, client service, operational, and leadership workflows
Create instructor-led training, virtual workshops, eLearning, microlearning, knowledge checks, simulations, and guided practice activities
Partner with Product Development and SMEs to ensure learning materials accurately reflect current system functionality and business processes
Understand Learning Needs
Conduct learning needs analyses with stakeholders, Product Development teams, and business SMEs
Identify knowledge gaps, skill gaps, workflow challenges, and adoption barriers
Adapt training programs to meet the needs of different employee populations and job roles
Prioritize learning solutions based on business impact and organizational needs
Learning Design & Content Development
Develop job aids, SOPs, quick reference guides, process maps, eLearning modules, instructional videos, facilitator guides, learner materials, and assessments
Create video-based learning using screen capture and editing tools
Maintain and continuously improve Dynamics 365 learning content and documentation
Conduct Training Sessions
Facilitate engaging virtual and in-person training programs
Deliver onboarding training to new hires and employees joining through acquisitions
Conduct webinars, workshops, office hours, refresher sessions, and individual coaching as needed
Support major system rollouts, upgrades, and new feature launches with targeted learning initiatives
Dynamics 365 Adoption & Enablement
Serve as the primary learning resource for Dynamics 365 training and best practices
Translate technical system updates into practical, business-focused learning experiences
Employee Benefits Technology Ecosystem Enablement
Maintain a working knowledge of the Employee Benefits technology ecosystem and how systems interact
Help employees understand the relationships between Dynamics 365 and integrated platforms such as Outreach and ZoomInfo
Develop training materials that demonstrate end-to-end workflows across multiple systems
Reinforce the importance of data quality and system-of-record practices within Dynamics 365
Product Development Partnership
Participate in system enhancement meetings and release planning efforts
Represent the learning and user adoption perspective during system change discussions
Know the Business You Serve
Build strong partnerships with Employee Benefits and HRC leaders, SMEs, producers, account teams, and operational stakeholders
Stay current on business priorities, workflows, client lifecycles, and industry trends
Ensure training clearly connects employee actions within systems to business outcomes and client impact
Evaluate Training Effectiveness
Measure learning effectiveness using participation, completion, knowledge, confidence, application, and feedback metrics
Conduct after-action reviews following major training initiatives and technology rollouts
Use learner and stakeholder feedback to continuously improve training effectiveness
Support Change Management Efforts
Help employees understand what is changing, why it matters, and how it impacts their work
Develop reinforcement and adoption strategies following training delivery
Serve as a trusted advisor to stakeholders during periods of organizational or technology change
Manage Training Resources
Manage multiple projects and priorities while meeting established deadlines
Qualifications, Skills and Requirements
Experience collaborating with Product Development teams, technology owners, and SMEs to develop learning solutions
Ability to create and facilitate engaging learning experiences for adult learners
Strong understanding of instructional design and adult-learning principles
Ability to translate complex technical concepts into practical, user-friendly learning experiences
Experience delivering technical systems training to diverse audiences
Strong stakeholder management and relationship-building skills
Expertise in learning content development including video creation and editing
Experience designing role-based and workflow-based technical training programs
Strong working knowledge of Microsoft 365, particularly Teams, Outlook, PowerPoint, Excel, and OneDrive
Experience with Learning Management Systems (LMS)
Excellent organizational, project management, and prioritization skills
Willingness and ability to travel as needed
Education, Training and Experience
Required
Bachelor's Degree or equivalent combination of education and experience
5+ years of experience in Employee Benefits (required), with additional experience in one or more of: Human Resources Consulting, Insurance or Financial Services, Technical Training, Learning & Development, Instructional Design, or Systems Training and Enablement
Advanced user, trainer, administrator, or power-user experience with Microsoft Dynamics 365
Experience supporting Dynamics 365 implementations, upgrades, or adoption initiatives
Experience facilitating instructor-led and virtual training programs
Experience developing technical learning content, job aids, and video-based learning
Experience partnering with SMEs and business leaders to identify learning needs and develop solutions
Experience managing multiple projects and stakeholders simultaneously
Preferred
Familiarity with Employee Benefits producer workflows, account management processes, client lifecycles, and reporting
Familiarity with HRC business processes and systems
Experience with integrated technologies such as Outreach, ZoomInfo, and related business platforms
Experience with AI-forward training tools and approaches
Knowledge of change management and adoption methodologies
Experience supporting onboarding and acquisition integration efforts
The typical base pay range for this role nationwide is $70,000 to $85