Demo

Territory Sales Representative

Progressive
Ashland, KY Full Time
POSTED ON 7/18/2026
AVAILABLE BEFORE 11/14/2026

Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun. Apply today and take the first step to Destination: Progress.

As a territory sales representative, you'll be the face of Progressive for independent agencies. In this role, you'll meet with agents in your assigned territory to influence and advocate for increased utilization of Progressive's products and services. You'll tailor your agent meetings to create opportunities to benefit both Progressive and the agency. As an account sales representative, you'll manage the quality of the book of business and overcome objections to drive profitable growth within your territory. By becoming a trusted partner, you'll learn the agency's goals and how our products fit into those goals. You'll be provided a company vehicle, phone, laptop, and company credit card.

Territory: Kentucky territory of Florence, Ashland, Middlesboro, Lexington and surrounding communities.

Home office location: Must live in Lexington or Ashland, KY or surrounding communities.

Travel Requirements: Candidates must be able to occasionally travel to and meet with all agencies within this geographic area. Overnight travel will be required within the territory (approximately 2-3 times per month). Additional overnights may take place for agent meetings/conferences or team meetings outside of the assigned territory. In addition, overnight travel will be required to attend training in either Ohio or Florida.

Our interview process for this position will include at least one in-person interview, if you advance after the phone interview.

Must-have qualifications
  • High School diploma/GED equivalent or higher and a minimum of 6 years outside business to business sales experience or territory management experience.
  • {OR} Bachelor's degree or higher and a minimum of 3 years outside business-to-business sales experience or territory management experience.
  • {OR} High School diploma/GED equivalent or higher and a minimum of 4 years of experience in a Progressive Agency Distribution Inside Sales Representative role.
  • {OR} Bachelor's degree or higher and a minimum of 1 year of experience in a Progressive Agency Distribution Inside Sales Representative role.
  • This position requires compliance with Progressive's driving standards and\or policy.
  • This position requires a valid driver's license and auto insurance.

Preferred skills
  • Outside business-to-business sales experience with a demonstrated ability to advocate, influence, and advance results and business outcomes
  • Ability to manage work and weekly schedule independently and efficiently- prior experience in a field-based role
  • Ability to use formal and informal networks to accomplish goals and review data sources
  • Proficient in Microsoft Office (i.e., Word, Excel, and PowerPoint)
  • Experience with a sales or customer relationship management tool (i.e., Salesforce)

Compensation
  • $90,000-$105,000/year
  • Gainshare annual cash incentive payment up to 30% of your eligible earnings based on company performance

Benefits
  • 401(k) with dollar-for-dollar company match up to 6%
  • Medical, dental & vision, including free preventative care
  • Wellness & mental health programs
  • Health care flexible spending accounts, health savings accounts, & life insurance
  • Paid time off, including volunteer time off
  • Paid & unpaid sick leave where applicable, as well as short & long-term disability
  • Parental & family leave; military leave & pay
  • Diverse, inclusive & welcoming culture with Employee Resource Groups
  • Career development & tuition assistance

Physical requirements and working conditions

The physical requirements and working conditions listed below are representative of those required on the job. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential duties and responsibilities.
  • May require lifting < 25 lbs.
  • Ability to work outdoors, including ability to tolerate extreme weather conditions.
  • Involves frequent driving.

Energage recognizes Progressive as a 2025 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

Applicants must be authorized to work for any employer in the U.S. without the need or potential need, of current or future sponsorship for employment. Progressive does not hire candidates with (e.g., F-1 CPT, OPT, or STEM OPT, H-1B, O-1, E-3, TN) statuses for this role.

For ideas about how you might be able to protect yourself from job scams, visit our scam-awareness page at https://careers.progressive.com/pages/how-we-hire-faq-job-scams/

#LI-CM1
#LI-Hybrid

Benefits:

401K Plan, Vacation & Paid Time Off, Health Insurance

Salary : $90,000 - $105,000

If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Territory Sales Representative?

Sign up to receive alerts about other jobs on the Territory Sales Representative career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$109,535 - $156,850
Income Estimation: 
$168,296 - $226,155
Income Estimation: 
$103,275 - $152,386
Income Estimation: 
$51,625 - $76,458
Income Estimation: 
$116,498 - $172,747
Income Estimation: 
$63,227 - $94,954
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Progressive

  • Progressive Colchester, VT
  • Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun. Apply today and take the first ... more
  • 12 Days Ago

  • Progressive Lexington, KY
  • Project Administrator - Transmission Construction Location: Hybrid in Lexington, KY Position Summary We are seeking a Project Administrator to provide admi... more
  • 12 Days Ago

  • Progressive Rochester, MN
  • Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun. Apply today and take the first ... more
  • 12 Days Ago

  • Progressive Wayne, NJ
  • Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun. Apply today and take the first ... more
  • 12 Days Ago


Not the job you're looking for? Here are some other Territory Sales Representative jobs in the Ashland, KY area that may be a better fit.

  • The H.T. Hackney Company Harold, KY
  • Job Summary We are seeking a dynamic and driven Territory Sales Representative to join our team and spearhead growth within designated regions. This role o... more
  • 12 Days Ago

AI Assistant is available now!

Feel free to start your new journey!