Outside Sales Representative & Trainer, Insurance Benefits
Overview
The Outside Sales Representative and Trainer owns a local territory, selling supplemental insurance to small and mid-sized businesses while training new agents. You build your own book of business and mentor others, leading from the front. This hybrid role combines field sales with hands-on coaching. You work with business owners, deliver group presentations, and guide reps through call reviews and prep sessions. What sets this apart: dual focus on personal quota and team development, with clear paths into senior leadership.
What You'll Do8
- 1Meet with business owners to assess needs and sell tailored supplemental insurance plans
- 2Present benefit packages to employee groups, handling questions and objections
- 3Shadow new reps in the field, offering live feedback and hands-on Salesforce coaching
- 4Run call reviews, prep sessions, and debriefs to improve team performance
- 5Help new reps set weekly activity goals and track progress in Salesforce
- 6Maintain and grow your own client book while guiding others to build theirs
- 7Collaborate with your manager to refine sales strategies and grow the team
- 8Follow up with clients on claims and coverage, ensuring long-term satisfaction
Requirements8
- 12+ years in outside sales or B2B sales, with a track record of closing deals
- 21+ year mentoring or training sales reps, either formally or informally
- 3Active Health & Life General Lines License or ability to obtain within 90 days
- 4Salesforce experience, including pipeline management and activity logging
- 5Comfort presenting to groups of 50+ people, with clear and confident communication
- 6Proven follow-through and organizational skills, managing multiple client accounts
- 7Bachelor's degree or equivalent experience in sales, leadership, or coaching
- 8Coachable attitude and commitment to helping others succeed
Salary Insight
Salary not disclosed in listing
Location
Required Skills
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