Dynamics 365 & Employee Benefits Systems Training Specialist - Remote

OneDigital

74d • $70,000 - $85,000 • Remote

About The Position

The Dynamics 365 & Employee Benefits Systems Training Specialist partners with Product Development teams, Employee Benefits (EB) and Human Resources Consulting (HRC) subject matter experts, and business stakeholders to identify learning needs and design training solutions that build employee proficiency and adoption of Microsoft Dynamics 365. The role translates system functionality and business processes into practical, engaging learning experiences for employees in their roles.

This position leads Dynamics 365 learning across the Employee Benefits and HRC practices, supporting new hires, existing employees, acquired teams, and ongoing system enhancements. It also connects employees to the broader Employee Benefits technology ecosystem by explaining how Dynamics 365 integrates with Outreach, ZoomInfo, and other connected technologies. The ideal candidate combines Employee Benefits knowledge, technical systems expertise, facilitation and instructional design capabilities, and relationship-building skills. The position is remote and requires eligibility to work in the United States without visa or residency sponsorship. Travel may be required as needed.

Requirements

• Bachelor's degree or equivalent combination of education and experience.
• At least 5 years of experience in Employee Benefits; this experience is required.
• 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 subject matter experts and business leaders to identify learning needs and develop solutions.
• Experience managing multiple projects and stakeholders simultaneously.
• Experience collaborating with Product Development teams, technology owners, and subject matter experts 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.
• Must be eligible to work in the United States without the need for work visa or residency sponsorship.

Nice To Haves

• 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.
• 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.

Responsibilities

• Design and deliver training programs for Microsoft Dynamics 365 and related Employee Benefits technology solutions.
• Develop role-based learning paths for 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 subject matter experts to keep learning materials accurate and current.
• Conduct learning needs analyses and identify knowledge gaps, skill gaps, workflow challenges, and adoption barriers.
• Adapt training to different employee populations and job roles, and prioritize learning solutions based on business impact and organizational needs.
• 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 improve Dynamics 365 learning content and documentation.
• Facilitate virtual and in-person training, including onboarding, webinars, workshops, office hours, refresher sessions, and individual coaching.
• Support system rollouts, upgrades, and new feature launches with targeted learning initiatives.
• Serve as the primary learning resource for Dynamics 365 training and best practices, translating technical updates into business-focused learning experiences.
• Maintain knowledge of the Employee Benefits technology ecosystem and teach employees how Dynamics 365 relates to Outreach, ZoomInfo, and other integrated platforms.
• Develop training that demonstrates end-to-end workflows across multiple systems and reinforces data quality and system-of-record practices in Dynamics 365.
• Participate in system enhancement meetings and release planning, representing learning and user adoption in system change discussions.
• Build partnerships with Employee Benefits and HRC leaders, subject matter experts, producers, account teams, and operational stakeholders; stay current on business priorities, workflows, client lifecycles, and industry trends.
• Connect employee system actions to business outcomes and client impact through training.
• Measure training effectiveness using participation, completion, knowledge, confidence, application, and feedback metrics; conduct after-action reviews and use feedback to improve training.
• Support change management by explaining what is changing and why, developing reinforcement and adoption strategies, and advising stakeholders during organizational or technology change.
• Manage multiple projects and priorities while meeting established deadlines.

Benefits

• Eligible employees are offered health, wellbeing, retirement, and other financial benefits.
• Paid time off.
• Overtime pay for non-exempt employees.
• Learning and development programs.
• Reimbursement of job-related expenses according to company policy.
• Employee perks and discounts may be available.
• Some roles may be eligible for variable compensation, commission, and/or annual bonus based on individual and/or company performance.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level