Insurance Sales Representative Jobs in Kentucky
Insurance Sales Representative jobs in Kentucky concentrate in personal lines, commercial property and casualty, life and health coverage, and Medicare supplement products, with demand running from entry-level agents to senior producers and agency managers. Louisville, Lexington, and Bowling Green are the busiest hiring markets, anchored by established carriers and agencies such as Humana, Anthem, and State Farm. Group benefits and Medicare Advantage sales are among the most sought-after specialties as Kentucky's insurer footprint continues to expand. Scan the live roles below and apply to whichever ones fit.
Find JobsOverview
Showing 5 of 25+ Insurance Sales Representative jobs
Insurance Sales Representative
About the Role
We're looking for a motivated Insurance Sales representative to join our team and make a real impact. You'll meet with business owners, managers, and employees to provide supplemental insurance solutions that protect what matters most.
This is a full-time, outside sales role with a focus on relationship-building, client support, and helping businesses and individuals secure their financial future.
What You'll Do
Build relationships and maintain your own book of business.
Conduct face-to-face consultations and group presentations (1100+ people).
Follow up on leads, schedule appointments, and respond to client needs.
Manage your schedule while collaborating with a supportive team.
Hit monthly and quarterly sales goals with guidance from your manager.
What We Offer
Comprehensive training and mentorship.
Weekly draw pay, plus commissions and bonuses.
Advancement, incentive trips, cash bonuses, and stock share opportunities.
Flexible schedule once you've built your client base.
Work in a collaborative, caring culture that feels like family.
Who You Are
Service-oriented, empathetic, and motivated by helping others.
Self-driven, resilient, and able to manage your own schedule.
Professional, positive, and relationship-focused.
Licensed in Health & Life (or willing to obtain license; reimbursement available).
Company:Cleft on the Rock
Compensation:$75,000 - $95,000 per year withdraw pay, commissions, and bonuses as an independent contractor
Schedule:MondayFriday, weekends as needed
Location:Remote/Hybrid, B2B Sales
Join Us
Help businesses and individuals protect what matters most while building a rewarding career. Apply today to become an Insurance Sales representative with Cleft of the Rock!
See All 25 Insurance Sales Representative Jobs in Kentucky
Find roles in Kentucky that match your experience and apply in just a few clicks.
Find JobsInsurance Sales Representative Jobs by City in Kentucky
Where Kentucky roles are concentrated, by current openings.
Insurance Sales Representative Job Market in Kentucky
A snapshot from current Kentucky openings, updated as new roles post.
Who's Hiring
- Cleft of the Rock10C
- State Farm5
- 360Care2
- Pioneer Agency1P
- Alexander & Schmidt1
Top Industries Hiring
- Insurance
- Consulting & Professional Services
What Kentucky Employers Look For
The qualifications that appear most often in insurance sales representative jobs across Kentucky.
- Active Kentucky Property and Casualty or Life and Health insurance producer license required
- Proven ability to prospect, quote, and close personal or commercial lines policies
- Strong knowledge of Kentucky insurance regulations and carrier product portfolios
- Experience using agency management or CRM platforms to track client activity
- Valid driver's license and reliable transportation for in-person client meetings
- Bachelor's degree in business, finance, or a related field preferred but not required
Insurance Sales Representative Jobs in Kentucky: Frequently Asked Questions
How do you become a insurance sales representative in Kentucky?
You must obtain a Kentucky insurance producer license through the Kentucky Department of Insurance before selling any policy. The process requires completing a state-approved pre-licensing education course, passing the relevant state licensing exam administered by Pearson VUE, submitting a license application, and passing a background check. Most agents start with a Property and Casualty or Life and Health license, and many pursue both to broaden the products they can sell.
Which companies hire insurance sales representatives in Kentucky?
Kentucky insurance sales representative roles are posted by Cleft of the Rock, State Farm, and 360Care and others right now, based on current listings on Migrate Mate as of September 2026. Kentucky's concentration of major health insurers, regional independent agencies, and national captive carriers keeps hiring active across Louisville, Lexington, and beyond throughout the year.
Which Kentucky cities have the most insurance sales representative jobs?
Louisville, Murray, and Lexington account for the largest share of insurance sales representative openings in Kentucky. Louisville leads because it is home to Humana's headquarters and a dense cluster of regional agencies, Lexington draws openings through its large employer base and growing commercial sector, and Bowling Green has seen steady growth tied to its expanding healthcare and manufacturing industries that need commercial and group benefit coverage.
Are there remote insurance sales representative jobs in Kentucky?
Yes, but they're less common than in purely desk-based fields since many insurance sales roles depend on in-person client relationships and local market knowledge. About 70% of insurance sales representative openings tied to Kentucky are remote or hybrid as of September 2026, reflecting a mix of models across employers. Roles focused on inbound leads, inside sales, or group benefit enrollment tend to offer the most remote flexibility.
How can I get hired as a insurance sales representative in Kentucky with little or no experience?
The most realistic entry path is obtaining your Kentucky insurance producer license first, which signals commitment and lets you start selling on day one. Large Kentucky carriers like Humana and Anthem run structured onboarding programs that pair new agents with experienced producers, and many independent agencies in Louisville and Lexington hire unlicensed candidates on a contingent basis while they complete pre-licensing coursework. Customer service roles at insurance offices, bank branches, or financial services firms are common lateral moves that give candidates enough product knowledge to qualify for junior sales positions.
Where can I find and apply to insurance sales representative jobs in Kentucky?
You can find and apply to insurance sales representative jobs in Kentucky on Migrate Mate, which lists current Kentucky openings updated regularly. Search the available roles, find the ones that match your license type, specialty, and preferred location, and apply directly to each posting that fits your background.
See All 25 Insurance Sales Representative Jobs in Kentucky
Find roles in Kentucky that match your experience and apply in just a few clicks.
Find Jobs