Remote Captive Insurance Manager Jobs in Chicago, IL

Agency Owners: Direct IMO Access, 120%-145% Comp, Leads & Top Carriers

Most insurance agents and agency owners eventually hit the same ceiling:

• Contracts are too low
• Lead flow is inconsistent
• Carriers are limited
• Support disappears after onboarding
• Recruiting is hard
• Growth depends entirely on doing everything alone

Taylored Legacy is opening a limited expansion opportunity for licensed agents, agency owners, and serious producers who want a direct path to the top of the IMO, stronger contracts, lead support, and a platform built for long-term agency growth.

This is not a basic sales job.

This is for people who want to build.

Why Agency Owners Are Looking at Taylored Legacy

Qualified producers and agency builders may access:

• 120%-145% contract opportunities based on production
• Direct IMO-level growth path
• Free lead options for qualified agents
• High-intent lead programs, including inbound TV lead opportunities
• Top carrier access
• Daily pay opportunities
• Non-captive platform
• Final expense, mortgage protection, life insurance, annuities, and Medicare expansion
• CRM and dialing support
• Training, mentorship, and leadership support
• Spanish and English market opportunities
• Opportunity to build and own your book of business

Why This Opportunity Is Different?

Most IMO offers sound the same.

Higher comp. Better leads. More support.

The difference is whether the platform can actually help you scale.

Taylored Legacy is built around three things agency owners care about:

1. Better Economics

If you are producing or building a team, your contract level matters. Qualified agents and agency owners may qualify for 120%-145% contracts based on production, carrier approval, state requirements, and product mix.

2. Better Lead Options

Lead flow is the lifeblood of an insurance agency. We offer lead options designed to help serious producers scale, including free lead opportunities for qualified agents and high-intent inbound lead programs.

3. Better Growth Path

This is a non-captive platform with leadership growth, agency-building support, carrier access, and expanding product lines. You are not just writing business. You are building equity, leadership, and long-term opportunity.

Who We Want

This may be a strong fit if you are:

• A licensed life insurance agent
• A final expense producer
• A mortgage protection agent
• An annuity producer
• A Medicare producer looking for expansion
• An agency owner with active agents
• A team builder who wants stronger contracts
• A producer tired of weak support and low contract levels
• A hard-working entrepreneur who wants to scale

Product Lines

Taylored Legacy supports growth across:

• Final expense
• Mortgage protection
• Life insurance
• Annuities
• Medicare division expansion
• English and Spanish markets

What You Get Access To

• Top carrier relationships
• Contract levels from 120%-145% based on production
• Lead options, including free lead opportunities for qualified producers
• Inbound TV lead opportunities
• CRM and dialing platform
• Training and onboarding support
• Leadership mentorship
• Recruiting and agency-building support
• Daily pay opportunities
• Non-captive structure
• Long-term book-of-business ownership opportunities

Limited Expansion Window

We are not looking for everyone.

We are looking for serious licensed agents, agency owners, and producers who understand that direct access, stronger contracts, and lead support can accelerate growth.

This opening will not remain available forever. Contract access, lead options, and direct expansion slots are limited and based on fit, production, licensing, and market availability.

Compensation

This is a commission-based 1099 opportunity.

Qualified producers may access contract opportunities ranging from 120% to 145% comp.

Income varies by individual performance, licensing, state approval, carrier approval, activity level, product mix, lead follow-up, and sales results. No income is guaranteed.

Quick Apply

Apply in under 2 minutes.

No long resume required.

If you are licensed, producing, or leading a team, apply now, and let’s see if Taylored Legacy is the right platform for your next level.

Taylored Legacy is a family-owned national insurance organization built to help agents and agency owners succeed while protecting families across the United States. Specializing in Final Expense, Mortgage Protection, Annuities, and Medicare, our team has helped protect hundreds of thousands of families and has paid over $200 million in commissions to the agents and entrepreneurs who represent us.

We are one of the fastest-growing independent marketing organizations in the insurance industry, powered by a proven system that combines exclusive inbound leads, daily compensation, contracts up to 145%, and true long-term book ownership on a fully non-captive platform.

Agents and agency owners choose Taylored Legacy because we deliver what others only promise. Our in-house lead generation includes high-intent TV, digital, and direct mail campaigns. Our compensation is transparent with daily payouts. Our training and mentorship programs are hands-on and ongoing. And our remote-first model gives producers the flexibility to build their business from anywhere.

We are committed to building careers and agencies, not just writing contracts. Whether you are a brand-new entrepreneur or a seasoned agency owner looking for a better home, Taylored Legacy provides the carriers, leads, technology, and support to help you reach your full potential.

Commission-based 1099 independent contractor opportunity. Income varies by individual performance and production level.