Agency Operations Trainer - Employee Benefits

Keystone Agency Partners LLC

2d • Remote

About The Position

The Agency Operations Trainer – Employee Benefits is responsible for developing, delivering, and maintaining high-quality training that enables consistent, efficient execution of Employee Benefits operations across the organization. This role focuses on Group Benefits (Small, Mid, and Large) and Individual Life & Health, helping employees understand how work is performed end-to-end—across workflows, systems, and servicing standards. The Trainer partners closely with Operations, Change Management, Product/Workflow leaders, and Technology teams to ensure training aligns to standard processes, system capabilities, and transformation priorities. This is a hands-on role, ideal for a strong Employee Benefits practitioner who enjoys teaching, coaching, and enabling others through practical, workflow-based learning.

Requirements

• 5+ years of experience in insurance operations, employee benefits servicing, or a related role
• Direct experience working in Employee Benefits, supporting Group and/or Individual Life & Health
• Practical understanding of end-to-end Employee Benefits workflows and servicing models
• Experience delivering training, coaching, or peer enablement in an operational environment
• Comfort presenting to groups and facilitating learning discussions
• Experience supporting system rollouts, process changes, or operational transformations
• Hands-on experience with Applied Epic for Employee Benefits required
• Familiarity with a modern insurance agency technology stack
• Strong communication skills with the ability to explain complex concepts clearly and practically
• Willingness to travel approximately 50-75%
• Ability to pass a criminal background check, as permitted by law

Nice To Haves

• Experience with Applied Benefit Designer highly desired

Responsibilities

• Deliver engaging, role-based training for Employee Benefits technology stack, including Applied Epic, Applied Benefit Designer, and other agency tools that support end-to-end workflows
• Facilitate system demos, workflow walk-throughs, onboarding sessions, and reinforcement/optimization training aligned to implementations, conversions, and rollout plans
• Gather feedback from learners, leaders, and support teams to identify training gaps or opportunities for improvement
• Develop and maintain training materials, including job aids, quick reference guide, playbooks, e-learning/microlearning content (as applicable)
• Support the translation of end-to-end Employee Benefits workflows into clear, practical guidance that integrates process + system usage + servicing standards
• Keep training content current with changes to workflows, systems, carriers, compliance requirements, and operating models
• Partner with Technology, Product/Workflow Owners, and Configuration teams to understand system updates and translate them into user-friendly training
• Work closely with Employee Benefits Operations leaders, Training & Development teammates, Change Management, Product / Workflow Owners, Technology and Field Support teams
• Ensure training reflects standard processes and aligns with broader operational and change initiatives
• Act as a trusted, approachable resource for employees learning new workflows or systems

Benefits

• Competitive Salary
• Health Insurance Plans (PPO, HSA, Copay Options)
• Dental Insurance
• Vision Insurance
• Company Paid Disability Insurance
• Supplemental Insurance including Critical Illness, Accident, Legal, Pet Insurance
• 401(k) with Safe Harbor Match
• Paid Time Off
• Paid Holidays

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed