Nurses, CNAs & Skilled Trades — Remote Life Insurance Agent (1099)

Serving Agawam, MA and Western Massachusetts, Shipley Legacy Group is hiring nurses, CNAs, home health aides, and skilled tradespeople who are ready to bring their gift for explaining hard things in difficult moments to 100% remote, commission-based 1099 life insurance work. This is a remote, work-from-home position — you'll work entirely from home on your own schedule while serving clients throughout the region.

What you'll actually do

• Contact prospective clients who've asked about life insurance coverage
• Schedule and hold coverage conversations by phone or video call
• Listen to each client's situation and explain available policy options clearly
• Help clients complete applications and track their cases through underwriting
• Work independently, setting your own hours around your current commitments
• Use call review resources and scripts available through the agency when you need them

Who this is a fit for

• Healthcare workers and tradespeople ready for a meaningful career shift
• People already comfortable having honest conversations about serious topic
• Self-directed individuals who don't need someone managing their daily schedule
• Those who hold a state life insurance license — or are willing to obtain one before selling
• Anyone with a computer, a phone, and reliable internet at home

What we provide

• Direct carrier appointments available through Shipley Legacy Group
• 1:1 mentorship available from day one alongside scripts and call reviews
• Weekly team call available to connect with the agency's 17 active agents
• Underwriting advocacy available when a client's case needs extra attention

The honest part

This is commission-only 1099 work — no hourly wage, no salary. Anissa and Joe Shipley started Shipley Legacy Group after losing close family members and learning firsthand what a missing policy costs a grieving family; if that mission resonates with the work you've already been doing, it's worth a conversation. If you need guaranteed pay right now, this isn't the right fit — if you don't, reach out and let's talk.

Ready to start a conversation? Send us a note with a bit about your background and why life insurance work appeals to you. We're hiring now and would love to hear from Western Mass healthcare and trades professionals who are ready to work remote.