Work-From-Home Sales Specialist — Field and D2D Sales Pros

The Wood Agency is hiring a Work-From-Home Sales Specialist in Winchendon, MA to sell life insurance remotely. This is a 100% remote, work-from-home position open to candidates in Winchendon, MA. You'll call people who requested coverage, handle discovery and closing on commission as a 1099 independent contractor, and stay with cases through policy issuance.

What you'll actually do

• Sell life insurance to families remotely, compensated by commission on a 1099 independent-contractor basis
• Call people who submitted a request for coverage — no territory routes, no windshield time
• Understand a family's actual situation before presenting anything, then walk through options and complete the application together
• Stay with the case through to issued policy, keeping the client informed while underwriting runs
• Log calls and notes in the CRM as you go and stay current on products across 43 represented carriers

Who this is a fit for

• Legally authorized to work in the United States
• Door-to-door, solar, or home services reps who close on commission and handle a "no" without losing their stride
• Comfortable holding a real conversation by phone — discovery first, presentation second
• Organized enough to track a case from first call to issued policy without needing someone to chase you
• Ready to sit for a state life insurance exam before making sales calls — or already cleared to sell

What we provide

• 1:1 mentorship with Ben and Andrea, who built The Wood Agency across all 50 states with 43 carrier relationships over five years
• Weekly team call, scripts, call reviews, and ride-alongs — available to you as you get started

The honest part

This is commission-based 1099 work — no base salary, and income is not guaranteed. If a fixed paycheck matters more than schedule freedom right now, that's a fair reason to pass. But if you've been grinding a physical territory for someone else's quota and you're ready to put those same skills to work from home, reach out to The Wood Agency and we'll walk you through exactly how it works.