Insurance Jobs in Lexington, KY
Insurance jobs in Lexington, Kentucky are concentrated in the downtown core, Hamburg Pavilion corridor, and the Beaumont business district, driven by steady demand from carriers, agencies, and the city's growing healthcare and equine industries. Employers actively hiring right now include State Farm, Kemper, and AMBA. See the openings below and apply to the ones that match your experience.
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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!
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Find Insurance JobsInsurance Job Market in Lexington
Who's Hiring
Top Industries Hiring
- Insurance
Insurance Jobs in Lexington: Frequently Asked Questions
How do I get an insurance job in Lexington?
Lexington's insurance market centers on independent agencies, regional carriers, and the large healthcare systems that self-insure and employ benefits specialists in-house. Candidates who focus on property and casualty lines, commercial accounts tied to the horse industry, or employee benefits for healthcare employers tend to move quickly through the hiring process here. Strong local networking through the Bluegrass Independent Insurance Agents association and experience with agricultural or equine clients gives applicants a meaningful edge in this market.
Which companies hire insurance professionals in Lexington?
Companies currently hiring insurances in Lexington include State Farm, Kemper, and AMBA, per current listings on Migrate Mate as of July 2026. Lexington's employer mix ranges from national carriers with regional offices downtown to independent agencies serving the surrounding Bluegrass farm and equine community.
Are there remote insurance jobs in Lexington?
Yes, though availability depends heavily on the role, with desk-based positions like underwriting, claims analysis, and policy servicing being far more remote-friendly than field sales or loss control work. About 100% of insurance openings tied to Lexington are remote or hybrid as of July 2026, reflecting a broad industry shift toward flexible work arrangements. Analytical and back-office roles at Lexington-based carriers and benefits administrators account for the largest share of those remote opportunities.
How can I get an insurance job in Lexington with little or no experience?
The most realistic entry path in Lexington is a customer service or policy servicing role at one of the city's independent agencies or regional carrier offices, where on-the-job training is common and advancement to licensed positions is expected. Employers in the Hamburg Pavilion and downtown corridors regularly hire candidates with strong communication skills and a willingness to pursue a Property and Casualty license. Entry-level claims intake roles at healthcare-affiliated insurers near the medical campus also offer a structured path into the industry.
Which industries hire the most insurance professionals in Lexington?
Lexington insurance roles concentrate in Insurance, based on current listings on Migrate Mate as of July 2026. Lexington's unique position as a hub for equine commerce, healthcare, and regional agriculture keeps demand across those sectors consistently above what you'd see in a comparable-sized city elsewhere.
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