Fleet Territory Sales Representative

Progressive Insurance; Maryland; On-site; USD 90,000 - 120,000; Full time

Benefits offered by this job

401(k) with company match up to 6%

Medical, dental & vision insurance

Paid time off and disability

Job summary

Progressive Insurance is seeking a territory sales representative (or senior) for its Fleet & Specialty programs. You will manage agencies in PA, NJ, NY, DE, WV, VA, and New England, driving growth and supporting the full sales process.

Travel is required, with at least 50% overnight trips. You’ll need to obtain a Property & Casualty license within 90 days, maintain eligibility with a valid driver’s license and auto insurance, and collaborate across underwriting and claims teams to

Qualifications

• Minimum 6 years outside business-to-business sales or territory management experience (or 3 years with a Bachelor's).
• License within 90 days and a valid driver’s license and auto insurance.
• This role requires compliance with Progressive driving standards and policies.

Responsibilities

• Manage agencies within a defined geographic region to drive premium growth.
• Develop relationships with agency leaders and production staff.
• Provide in-person education on fleet products and sales/marketing support.
• Coordinate collaboration among agencies, underwriting and claims teams.

Skills

Outside B2B sales

Territory management

Agency relationship development

Driver's license

Education

Bachelor's degree

High school diploma or GED

Tools

Property & Casualty license

Insurance certifications (ARM CIC TRIP TRS)

Job description

Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun.

As a territory sales representative or senior territory sales representative for Progressive Fleet & Specialty programs, you’ll focus on commercial mid and large fleet insurance product offerings. In this role, you’ll manage agencies within a specific geographic region to support premium growth and the overall sales process. You’ll develop relationships with agency leaders and production staff, provide in-person education on fleet products and provide sales and marketing support with insureds and prospective insureds. In addition, provide assistance with collaboration between the agency, underwriting and claims teams.

This role will require you to obtain a Property & Casualty insurance producer license within 90 days of starting position.

Territory: PA, NJ, NY, DE, WV, VA, and the New England states

Home office location: Philadelphia, PA; Baltimore, MD; Newark, NJ or surrounding communities

Travel Requirements: Candidates must be able to travel to and meet with all appointed agencies and their respective marketing and production teams within this geographic area. There is overnight travel with this position (minimum of 50%). Additional overnight travel may take place for conferences, special events or team meetings

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

Minimum 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
• Outside commercial insurance sales or marketing experience in fleet trucking industry
• Licensed Property & Casualty insurance producer.
• Insurance industry certifications (ARM, CIC, TRIP, TRS).
• Ability to use formal and informal networks to accomplish goals.

Compensation

• $90,000-$120,000/year depending on position level and experience
• 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

• Ability to work outdoors, including ability to tolerate extreme weather conditions.
• Involves frequent driving.

Energage recognizes Progressive as a 2026 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

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.