Digital Experience and Transformation Training Manager

Digital Experience and Transformation Training Manager

Location: Remote US

Type: Contract-to-Hire
Category: Program/Project Management
Industry: Insurance
Workplace Type: Remote

Job Description:  

Our client in the Insurance industry is looking for a dynamic professional to bridge the gap between technology, people, and process during a critical digital transformation journey. This hybrid role blends hands-on technology training with enterprise change management, ensuring employees adopt new digital tools (e.g., Microsoft 365, AI tools) while embracing lasting mindset and behavior shifts. You'll play a pivotal role in transforming how 1,200+ employees work, learn, and adapt in a tech-forward insurance environment. (Initial training focus is around AI tools)

** Remote **

Pay rate: $65-$80/hr W2 

Due to client requirement, applicants must be willing and able to work on a w2 basis. For our w2 consultants, we offer a great benefits package that includes Medical, Dental, and Vision benefits, 401k with company matching, and life insurance.  

Responsibilities:

Digital Training & Adoption

• Design, develop, and deliver engaging training for Microsoft Office 365 (Word, Excel, Outlook, Teams) and emerging AI tools (e.g., Copilot, ChatGPT).
• Create self-service learning materials: quick guides, videos, tutorials, and FAQs.
• Deliver live, virtual, and on-demand sessions tailored to diverse employee roles.
• Promote best practices for IT productivity, collaboration, and secure digital behavior.
• Respond to training-related support needs and gather feedback to continuously improve user education.

2. Change Management & Transformation Support

• Lead change management strategies for digital initiatives, including enterprise platform rollouts (e.g., ERP, CRM).
• Develop and implement scalable, role-specific change and training plans aligned with business objectives.
• Conduct readiness assessments, track adoption metrics, and proactively manage resistance.
• Communicate “the why” behind change clearly and consistently across the organization.
• Partner with leadership, HR, IT, and compliance to embed behavioral change into daily workflows.

3. Stakeholder Engagement & Enablement

• Build trust and alignment across departments and with senior leadership.
• Act as a strategic advisor to business units undergoing technology change.
• Facilitate forums, Q&A sessions, and workshops to promote engagement and feedback loops.
• Align efforts to the broader transformation roadmap and digital maturity goals.

4. Measurement, Risk, and Continuous Improvement

• Monitor training outcomes using pre/post assessments, surveys, and usage metrics.
• Generate insights to inform strategic improvements in user experience and adoption.
• Maintain dashboards and reports that show progress toward digital fluency and transformation KPIs.

Experience Requirements:

Experience:

2+ years in IT training or user support in a corporate setting; Change management experience preferred

Tech Skills:

Expertise with Microsoft Office 365, Teams, Outlook, SharePoint; experience using AI productivity tools

Change Management:

Understanding of Prosci/ADKAR or similar methodologies highly preferred

Soft Skills:

Organized, patient, empathetic communicator with strong presentation and facilitation ability

Documentation:

Skilled in creating training content, SOPs, and visual aids for diverse learners

Preferred:

• Experience supporting digital transformation in an insurance, healthcare, or highly regulated environment
• Experience tracking adoption, analyzing feedback, and adjusting strategies accordingly
• Certifications: Prosci, PMP, Agile/Scrum, Microsoft Certified Trainer (MCT)

Education Requirements:

Associate or Bachelor’s in IT, Organizational Development, Communications, or related field

Skills, experience, and other compensable factors will be considered when determining pay rate. The pay range provided in this posting reflects a W2 hourly rate; other employment options may be available that may result in pay outside of the provided range.
W2 employees of Eliassen Group who are regularly scheduled to work 30 or more hours per week are eligible for the following benefits: medical (choice of 3 plans), dental, vision, pre-tax accounts, other voluntary benefits including life and disability insurance, 401(k) with match, and sick time if required by law in the worked-in state/locality.
Please be advised- If anyone reaches out to you about an open position connected with Eliassen Group, please confirm that they have an Eliassen.com email address and never provide personal or financial information to anyone who is not clearly associated with Eliassen Group. 

About Eliassen Group: 

Eliassen Group is a leading strategic consulting company for human-powered solutions. For over 30 years, Eliassen has helped thousands of companies reach further and achieve more with their technology solutions, financial, risk & compliance, and advisory solutions, and clinical solutions. With offices from coast to coast and throughout Europe, Eliassen provides a local community presence, balanced with international reach. Eliassen Group strives to positively impact the lives of their employees, clients, consultants, and the communities in which they operate.

Eliassen Group is an Equal Opportunity/Affirmative Action Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, pregnancy, sexual orientation, gender identity, national origin, age, protected veteran status, or disability status.