Employee Benefits Trainer (Contractor)

BenefitPoint Trainer – Employee Benefits | Contract 2 Year

Location: Remote (Travel as Needed)

Overview

Join Alera Group's Transformation Office and help prepare our Employee Benefits teams for a major enterprise transformation.

As a BenefitPoint Trainer – Employee Benefits, you'll develop and deliver engaging, role-based training that helps colleagues confidently adopt BenefitPoint, related EB tools, and standardized business processes. You'll combine hands-on BenefitPoint expertise with strong facilitation skills to help employees understand not only how to use the technology, but how new workflows and processes come together in their day-to-day work.

You'll partner with the transformation team, subject matter experts, and change management teams to support implementation, adoption, and ongoing learning across a multi-office environment.

About Alera Group

Founded in 2017, Alera Group is one of the nation's leading independent insurance and financial services firms. We combine the strength of a national organization with the personalized service of local experts to help clients succeed in Employee Benefits, Property & Casualty, Retirement Plan Services, Wealth Services, and Human Capital Solutions.

• Develop and facilitate role-based training for Vertafore BenefitPoint, related EB tools, enterprise workflows, and standardized business processes.
• Deliver engaging instructor-led training in both virtual and in-person environments.
• Create training paths for different Employee Benefits roles and user groups.
• Help colleagues transition from existing systems and processes to new enterprise workflows while reinforcing adoption.
• Deliver new-hire onboarding for Employee Benefits system users.
• Provide post-transition reinforcement training and advanced feature workshops.
• Maintain expert-level knowledge of BenefitPoint, EB supporting tools, workflows, SOPs, and integrated applications.
• Stay current on platform enhancements and evaluate how system changes should be incorporated into training.
• Gather user feedback, identify knowledge gaps, and continuously improve training effectiveness.
• Partner with subject matter experts, transformation leaders, and change teams to deliver a consistent learning experience across offices.

Required

• Bachelor's degree or equivalent combination of education and relevant work experience
• 5+ years of hands-on BenefitPoint experience within an insurance agency or brokerage
• 3+ years of experience delivering technical or business systems training
• Strong understanding of Employee Benefits insurance operations, workflows, and terminology
• Strong presentation and facilitation skills, with experience engaging different audiences and learning styles
• Experience delivering training in virtual and/or instructor-led environments
• Excellent written and verbal communication skills
• Ability to translate complex BenefitPoint functionality and business processes into clear, practical learning
• Experience creating training materials using Microsoft Office and learning technologies

Preferred

• Experience training BenefitPoint as part of an implementation, conversion, migration, or large-scale rollout
• Experience developing role-based training paths or curricula for different user groups
• Experience supporting change management and user adoption initiatives
• Knowledge of adult learning principles and training best practices
• Experience using learner feedback, assessments, or adoption data to improve training effectiveness

Assignment Details

• Employment Type: Temporary Contract (Hourly)
• Duration: Approximately 2 years
• Schedule: Full-time
• Work Arrangement: Remote with travel as needed
• Opportunity to support one of Alera Group's largest enterprise transformation initiatives while working alongside business, technology, training, change, and implementation leaders

Compensation

The anticipated hourly rate for this contract position is $70.00–$85.00 per hour, based on experience, qualifications, and relevant expertise.

What You'll Gain

• Play a key role in a large-scale enterprise transformation
• Help shape how Employee Benefits colleagues learn and adopt BenefitPoint and new enterprise workflows
• Deliver training across a broad, multi-office Employee Benefits organization
• Work alongside business, technology, implementation, and change teams
• See the direct impact of your training as offices transition to new systems and ways of working

Work Environment

This role is primarily remote, with travel to Alera Group offices or project locations as needed for training, implementation, and other project activities.

Training will be delivered in both virtual and in-person environments, and the role may support multiple offices and implementation waves. Success requires strong facilitation skills, adaptability, organization, and the ability to build confidence with users navigating significant technology and process change.

We're an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected class.

Alera Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process.

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