Insurance Sales Coach

trainwell

Anywhere$180,000 - $220,000 / yearSales & Partnerships

Trainwell is the premier sales training and implementation company for insurance agencies. We work with top-producing agents — many ranked in the top 10 nationally — to scale their production, build accountability systems, and transform their teams into elite closers.

Our coaching is built on the 4 Pillars: needs-based sales process, accountability and management, marketing and lead ROI, and hiring and ramp. We don't do fluff. We don't recycle 2014-era training. We install systems that produce measurable results — and our clients pay a premium for it.
We're scaling fast, and we're hiring a Coach to work directly with our highest-tier clients.

The Role

As a Trainwell Coach, you'll work 1-on-1 and in group settings with insurance agents and their teams to drive production, install systems, and build winning sales cultures. This is not a babysitting role. You'll be expected to deliver outcomes — and you'll have the platform, IP, and team behind you to do it.

What You'll Do

  • Coach insurance agents and team members through structured 3-month engagements

  • Install needs-based sales processes built around the Golden Multiline Script

  • Diagnose and fix breakdowns in sales process, accountability, hiring, and lead ROI

  • Build and refine accountability systems for agency teams

  • Lead live group calls, roleplay sessions, and 1-on-1 coaching

  • Review recorded sales calls and deliver actionable feedback

  • Help clients hire, ramp, and retain top-performing team members

  • Identify upgrade opportunities and move clients into higher-tier programs

  • Contribute to the evolution of Trainwell's IP, curriculum, and coaching methodology

What You Get

  • $180K–$220K+ earning potential (base + performance compensation)

  • Fully remote — work from anywhere

  • Direct access to Trainwell's IP, frameworks, and proprietary tools (including AI George)

  • Growth inside a company scaling toward 8 figures

  • Real ownership of client outcomes

  • A seat at the table with the team redefining insurance sales training

Requirements

What We're Looking For
Required:

  • Experience as a captive insurance agent, agency team lead, or top-producing team member

  • Documented track record of elite production

  • Deep understanding of multiline insurance sales — auto, home, life, financial services

  • Ability to coach, teach, and develop people (not just close)

  • Strong systems thinking — you build processes, not just hit numbers

Highly Preferred:

  • Experience hiring, ramping, and managing licensed team members

  • Background in life and financial services production

  • Prior coaching, training, or sales management experience

  • Comfort with technology (GHL, AI tools)

  • Fitness, military, or athletics background

You Are:

  • Hungry, humble, and coachable

  • Obsessed with winning and incapable of accepting average

  • Direct in your communication — you tell people the truth even when it's uncomfortable

  • A lifelong learner who has invested significantly in your own growth

Benefits

  • Remote

  • Base Salary

  • Commission

  • Performance Bonuses

  • Health Insurance

  • 401k with match & Roth 401k

  • PTO, Life Insurance, Disability Insurance