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.
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Insurance Sales Representative & Trainer
About Us
At Cleft of the Rock, we provide businesses and individuals with supplemental insurance solutions that protect what matters most. Our team values integrity, responsibility, and a genuine desire to serve, creating a culture where professionals who care about doing the right thing and helping others can thrive.
Your Role
As an Insurance Sales Representative & Trainer, you will combine your commitment to excellence with a service-minded approach. You will guide clients through insurance solutions with clarity and care, ensuring they understand their options and feel confident in their decisions. You will also mentor and support your team, helping them succeed while upholding high standards.
Key Responsibilities:
Meet with business owners, managers, and employees to present insurance solutions clearly and thoughtfully
Conduct individual consultations and group presentations for teams of various sizes
Build and maintain your own book of business with careful attention to client needs
Train and mentor new team members, providing guidance with both professionalism and support
Follow up on leads, maintain client relationships, and ensure a positive experience for every client
Collaborate with management to set goals, track performance, and uphold best practices
What We Offer
Comprehensive training and mentorship focused on excellence and service
Weekly draw pay, plus commissions and bonuses
Incentives including cash rewards, stock options, and recognition programs
Opportunities for career advancement and professional growth
A structured, supportive environment where quality, integrity, and client care are valued
Who You Are
Principled, detail-oriented, and committed to serving clients and team members with excellence
Reliable, ethical, and motivated by helping others make the right decisions
Professional, patient, and skilled at building trust while maintaining high standards
Independent yet collaborative, with a focus on meaningful impact
Licensed in Health & Life or willing to obtain a license (reimbursement provided)
Company:Cleft of the Rock
Compensation:$85,000 - $105,000 per year withdraw pay, commissions, and bonuses
Schedule:MondayFriday, weekends as needed
Location:In-person, business-to-business and individual sales
Join Us
This is a career where you can serve clients, support your team, and make a lasting impact while upholding high standards. Cleft of the Rock provides the tools, training, and culture you need to succeed as an Insurance Sales Representative & Trainer.
See All 15 Insurance Sales Representative Jobs in Kentucky
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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
Top Industries Hiring
- Insurance
- Technology & Software
- 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 State Farm, Cleft of the Rock, and Arcare and others right now, based on current listings on Migrate Mate as of November 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, Bardwell, and Mayfield 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 50% of insurance sales representative openings tied to Kentucky are remote or hybrid as of November 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 15 Insurance Sales Representative Jobs in Kentucky
Find roles in Kentucky that match your experience and apply in just a few clicks.
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