Remote Whole Life Insurance Agent — Career Changers From Healthcare & Skilled Trades (1099)

Decorah, IA — You've worked beside people when life goes sideways — on a floor, in the field, or on a job site. Shipley Legacy Group was started by Anissa and Joe Shipley after both lost close family members, and this agency exists because of it. This is a remote, work-from-home position serving the Decorah, IA area. It's 100% remote, commission-based 1099 life insurance sales for career changers who want that to mean something.

What you'll actually do

• Contact prospective clients and schedule coverage conversations from home, on your schedule
• Listen to what a family needs and explain whole life insurance options in plain terms
• Help clients complete applications and follow each case through underwriting
• Use available scripts and call reviews to sharpen how you talk about coverage
• Tap into a 1:1 mentor available through Shipley Legacy Group as you find your footing
• Manage your own pipeline and follow up consistently — no one does that part for you

Who this is a fit for

• Healthcare workers or tradespeople ready to stop letting the shift schedule run their lives
• People who've watched a family scramble after a loss and want to help others avoid that
• Career changers willing to obtain a state life insurance license before selling
• Self-directed adults who can work without supervision or a time clock
• Anyone already comfortable talking to people about serious, real-life topics
• Those who understand flexibility and commission-only pay go hand in hand

What we provide

• Direct carrier appointments available upon joining the team
• 1:1 mentorship and access to weekly team calls available through Shipley Legacy Group
• Scripts, call reviews, and ongoing training available as you build your practice
• Underwriting advocacy to help your clients' cases move forward

The honest part

This is commission-only 1099 work — no salary, no guaranteed income. Shipley Legacy Group has 17 agents and six years in business, but this role isn't for everyone: if you need a steady paycheck while you get started, that's worth knowing now. If the work sounds right, apply below and let's talk.

Ready to turn your experience into a career that fits your life? Apply now and connect with the Shipley Legacy Group team. We're building something real in Decorah and beyond.