Senior Territory Sales Representative Commercial-Fleet

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Territory Sales Representative – Senior for Progressive Fleet & Specialty programs focuses on commercial mid‑ and large‑fleet insurance product offerings. In this role you will manage agencies within a specific geographic region to support premium growth and drive the overall sales process. You will develop relationships with agency leaders and production staff, provide in‑person education on fleet products, and deliver sales and marketing support to insureds and prospective insureds.

Additionally, you will collaborate with the agency, underwriting, and claims teams.

Responsibilities include obtaining a Property & Casualty insurance producer license within 90 days of starting and traveling to meet with all appointed agencies and their marketing and production teams (50%–70% overnight travel, with additional travel for conferences, special events, or team meetings).

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

• Philadelphia, PA;
  Baltimore, MD;
  Newark, NJ; or surrounding communities

• Must be willing to travel extensively within the territory (50‑70% overnight travel, additional travel for conferences or special events)

At least one in‑person interview after the phone interview if you advance.

• High School diploma/GED equivalent or higher with a minimum of eight years of outside business‑to‑business sales or territory management experience.
• OR Bachelor’s degree or higher with a minimum of five years of outside business‑to‑business sales or territory management experience.
• Compliance with Progressive’s driving standards and policy.
• Valid driver’s license and auto insurance.

• Experience in outside business‑to‑business sales with demonstrated ability to influence and advance results.
• Experience in outside commercial insurance sales or marketing in the fleet trucking industry.
• Licensed Property & Casualty insurance producer.
• Insurance industry certifications (ARM, CIC, CPCU, TRIP, TRS).
• Ability to leverage formal and informal networks to achieve goals.

• $100,000 – $113,000 per year.
• Gainshare annual cash incentive up to 30% of eligible earnings based on company performance.

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

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

Equal Opportunity Employer.

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Mid‑Senior level

Full‑time

Sales and Business Development

Insurance