Employee Benefits Systems Trainer - Remote

Digital Insurance LLC; United States; Remote; USD 70,000 - 85,000; Full time

Benefits offered by this job

Health benefits

Learning & development programs

Travel opportunities

Job summary

OneDigital is seeking a Dynamics 365 Training Specialist to partner with Product Development, Employee Benefits, and HR Consulting teams. You will translate complex system updates into practical, engaging learning experiences for diverse employees, and lead programs that drive proficiency and adoption across the Dynamics 365 ecosystem.

The role focuses on new hires, acquisitions, and ongoing system enhancements, including integration with Outreach and ZoomInfo. Travel may be required.

Qualifications

• 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

Responsibilities

• Design and Develop Training Programs for Dynamics 365 and related Employee Benefits technology
• 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 reflect current system functionality and business processes
• Conduct learning needs analyses with stakeholders and SMEs
• Identify knowledge gaps, workflow challenges, and adoption barriers
• Adapt training programs for different employee populations and job roles
• Prioritize learning solutions based on business impact
• 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
• Facilitate engaging virtual and in-person training programs
• Deliver onboarding training to new hires and acquisitions
• Conduct webinars, workshops, office hours, refresher sessions, and coaching
• Support major system rollouts, upgrades, and new feature launches with targeted learning initiatives
• Serve as the primary learning resource for Dynamics 365 adoption and best practices
• Translate technical updates into practical learning experiences
• Know the business you serve and build partnerships with leaders, SMEs, and stakeholders
• Evaluate training effectiveness using metrics and after-action reviews
• Support change management efforts and adoption strategies
• Manage training resources across multiple projects

Skills

Learning & development

Instructional design

Stakeholder management

Microsoft Dynamics 365

Video-based learning

Education

Bachelor's Degree or equivalent

Tools

Microsoft Dynamics 365

Outreach

ZoomInfo

Microsoft 365 (Teams, Outlook, PowerPoint, Excel, OneDrive)

Learning Management System (LMS)

Job description

Are you looking to accelerate your career without having to hide your authentic self - a place where you can be you? A career that’s making a bigger impact on the world? At OneDigital, we are on a mission to help people do their best work and live their best lives. From the services we offer to the way we show up for each other each day, we are fueling dreams, achieving big goals, and embracing each other’s truest selves.

We understand that pursuing a new job is a big deal. Maybe you’re afraid you won’t fit in. Well, here’s the good news. For us, the days of “fit in to get in” are over and being different is not a barrier to getting ahead. Greatness comes in all shapes, sizes, colors, and experience levels. If you are looking for a people-first culture that is wired for growth, driven to serve, and totally committed to having your back, give us a shot.Your best life awaits.

Must be eligible to work in the United States without the need for work visa or residency sponsorship.

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 $85,000 per year.

Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company’s performance. We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non-exempt employees, and robust learning and development programs. You will receive reimbursement of job-related expenses per the company policy and may receive employee perks and discounts.

To learn more, visit: www.onedigital.com/careers

OneDigital is an equal opportunity employer. Not only as a matter of standard, but to honor and celebrate our differences. We believe that the power of ONE starts with you. We are committed to cultivating and preserving a culture that celebrates diversity, insists on equity and inclusion, and connects us. Ensuring our people feel seen, valued, respected, and supported is fundamental to our core values and business goals.

OneDigital provides equal employment opportunities to all employees and applicants for employment regardless of their: veteran status, uniformed servicemember status, race, color, religion, sex, sexual orientation, gender identity, age (40 and over), pregnancy (including childbirth, lactation and related medical conditions), national origin or ancestry, citizenship or immigration status, physical or mental disability, genetic information (including testing and characteristics) or any other category protected by federal, state or local law (collectively, “protected characteristics”). A copy of the Federal EEO poster is linked here.

Pursuant to local Fair Chance Ordinances, we will consider qualified applications with arrest or conviction records for employment. For applicable candidates, the following ordinances are linked here to inform you of your rights as an applicant:

City and County of San Francisco

City of Los Angeles

County of Los Angeles

Employment decisions shall comply with all other applicable federal, state and city/county laws prohibiting discrimination in employment. OneDigital complies with all criminal history inquiry [or ‘ban the box’] laws in California, Connecticut, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New Mexico, Oregon, Rhode Island, Vermont and Washington.

In short, we believe in hiring the most qualified applicant for the position, regardless of background.

This posting will remain live while OneDigital is actively accepting applications. Once candidates have been selected, the posting will be removed.

OneDigital understands the immense responsibility and opportunities provided by Artificial Intelligence. We utilize advanced Artificial Intelligence [AI] technologies to enhance our recruitment process. This includes using AI to filter candidates based on their qualifications and to rediscover potential candidates from our existing applicant pool. Our AI systems help us efficiently identify the best fit for our open positions, ensuring a streamlined and effective hiring experience. However, AI does not replace the humans in our process. If you have concerns about our use of AI, you may opt out where laws allow.

If you have questions about our hiring policies and practices, we would be happy to discuss upon receiving your application. We hope to welcome you to OneDigital and look forward to hearing from you.

Thank you for your interest in joining the OneDigital team!