The Wood Agency Life
Remote Sales Representative — Career Changers Welcome
Role: Sales Representative
Remote life insurance sales — specifically final expense coverage — is the work The Wood Agency is hiring for in the Pittsfield, MA area. This is a 100% remote, work-from-home position. The role suits career changers who can hold an honest conversation with older adults and their families, follow through consistently, and work without someone looking over their shoulder.
What you'll do
- Call or message people who have already asked about final expense coverage and set up a time to talk
- Ask the right questions first — health situation, budget, what they're trying to protect — before you ever mention a plan
- Walk through coverage options and complete the application together by phone or video
- Log every conversation and next step in the CRM while the case is still fresh
- Keep clients informed as their application moves through the carrier's review process, all the way to a decision
- Stay current on product and carrier training — this continues well past your first month
Qualifications
- Legally authorized to work in the United States
- A state life insurance license — or the ability to get one before you begin selling
- Comfort carrying detailed conversations over the phone or on video, with people you've never met
- Able to navigate web-based tools: e-applications, quoting systems, a CRM
- You manage your own schedule and keep your own pipeline moving without reminders
- Resilient when a case doesn't close — and willing to follow up anyway
What we provide
- Access to 43 carriers, so you can match clients to coverage that actually fits rather than pushing one product
- An exclusive lead system is available to agents — ask about it during your conversation
- Weekly team call, scripts, call reviews, and ride-alongs available as you get started
- 1:1 mentorship available through The Wood Agency's founders, who work directly with agents on the team
Compensation
This is a 1099 independent contractor role. Compensation is commission-based. No salary or hourly pay is provided. Earnings depend on individual production. If that structure fits where you are right now, The Wood Agency welcomes your application.
Apply directly to The Wood Agency Life
Interested in this role?
Send your information to the hiring team. This opening is accepting applications through October 19, 2026.