The Progressive Corporation

Fleet Territory Sales Representative

The Progressive Corporation$90K — $120K *
Finance & Insurance
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • High School diploma/GED and 6+ years in outside B2B sales or territory management, or a Bachelor's degree with 3+ years in similar roles.
  • Alternatively, a minimum of 4 years as a Progressive Agency Distribution Inside Sales Representative with a high school diploma, or 1+ year with a Bachelor's degree.
  • Compliance with driving standards and possession of a valid driver's license is required.
  • Experience advocating and influencing in outside B2B sales is preferred.
  • Previous exposure to commercial insurance sales within the fleet trucking sector is valued.

Responsibilities

  • Manage agency relationships within specified regions to drive premium growth.
  • Educate agency leaders and teams on fleet insurance products.
  • Provide sales and marketing support to insureds and prospects.
  • Collaborate with underwriting and claims teams for effective operations.
  • Travel to meet with appointed agencies and attend relevant conferences.

Benefits

  • 401(k) with company match up to 6%.
  • Comprehensive medical, dental, and vision plans, including free preventive care.
  • Wellness and mental health program offerings.
  • Flexible spending and health savings accounts available.
  • Generous paid time off which includes volunteer opportunities.
  • Short and long-term disability, as well as sick leave, are provided.
  • Parental leave and support for military personnel, if applicable.
  • Commitment to diversity and inclusion with supportive Employee Resource Groups.
  • Tuition assistance and growth opportunities for career development.
Full Job Description
As aterritory 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-termdisability
  • 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 2026 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

About The Progressive Corporation

Progressive is a place where innovation and collaboration are a way of life. Each of our employees has a role in our success and together, we continue to find new and better ways to satisfy our customers and move the insurance industry forward.

The Progressive Corporation Careers

Join the vibrant team at The Progressive Corporation, a leader in the insurance industry, and propel your career to new heights with a company known for innovation, leadership, and a commitment to diversity and growth.

Work You’ll Do

At The Progressive Corporation, we offer more than just job opportunities; we provide a platform for professional development and personal growth. As part of our team, you will contribute to transformative projects that redefine the standards of the insurance industry. Our collaborative culture ensures that every team member has the opportunity to make a significant impact.

Empower Your Career

Step into a role that challenges and excites you. At Progressive, you can navigate through a variety of career paths with the support of our extensive training and development programs. From leadership training to diversity workshops, we equip our professionals with the tools they need to excel.

Innovate with Us

Join a group of forward-thinkers who are constantly driving innovation in the insurance sector. At Progressive, your skills in technology, industry expertise, and digital innovation will help shape solutions that meet the evolving needs of our customers.

Internship Programs

Kickstart your career with The Progressive Corporation’s internship programs. Gain invaluable experience, build your resume, and develop professional networking connections that will benefit your career for years to come. Our internships offer a deep dive into the insurance industry, providing a robust foundation for future success.

Benefits and Culture

Choose a career with The Progressive Corporation and enjoy a wealth of benefits that go beyond the basics. Our inclusive culture supports our employees’ life stages and fosters a workplace where everyone can thrive. Health, wellness, financial planning, and work-life balance are just the beginning of what we offer.

Join Our Team

Explore the numerous positions available at Progressive, from entry-level to executive, and find where your expertise can make the most impact. We are continuously hiring talented individuals who are passionate about making a difference and ready to contribute to our culture of continuous improvement.

Stay Connected

Keep up to date with the latest at Progressive: - **Career Insights**: Get insider perspectives and industry-leading insights through our careers blog. - **Job Alert Emails**: Customize your subscription to receive job alerts and news tailored to your preferences. Discover the exciting and rewarding opportunities that await at The Progressive Corporation.

Explore Job Opportunities

Search open positions that match your skills and interests. We look for curious, creative, and solution-driven team players who are eager to drive progress and thrive in a dynamic environment.

SEARCH PROGRESSIVE JOBS

At The Progressive Corporation, your career is what you make of it. Grow, innovate, and lead with us as we redefine the future of insurance. Join us and be part of a team that values diversity, innovation, and the professional growth of its members.
Learn more about The Progressive Corporation
Size
49,000 employees
Market Cap
$75.6 billion
Industry
Net Income
$5.7 billion
Founded
1937
5 Year Trend
+15.3%
Revenue
$42.6 billion
NASDAQ

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