Progressive vs Pie Insurance: A Complete Small Business Insurance Comparison for 2026

As a small business owner, choosing the right insurance provider is crucial for protecting your company and employees. Let's compare two major players in the commercial insurance space: Progressive and Pie Insurance, focusing on their workers' compensation and business insurance offerings.

Company Overview

Progressive is one of America's largest insurance companies, currently ranking as the #2 auto insurer in the United States behind State Farm. Founded in 1937 by Jack Green and Joseph M. Lewis, the company is headquartered in Mayfield, Ohio.

Progressive offers a comprehensive range of insurance products, including:

Commercial vehicle insurance
Business property coverage
Workers' compensation
Other business-related policies through select partners

Workers' Compensation Insurance Landscape [1]

Before diving into the specifics of each provider, it's important to understand the current workers' compensation insurance market:

Most states require employers to purchase workers' compensation insurance to protect employees injured on the job. This insurance protects business owners from their statutory obligation to provide coverage for employees who experience work-related injuries or illnesses on business premises or due to business operations. Nearly all U.S. states mandate employers to carry this coverage.

Typically, workers' compensation insurance covers:

Medical expenses
Rehabilitation costs
Lost wages for injured employees

Market Trends and Pricing [2]

Recent market data reveals interesting trends in the workers' compensation insurance sector:

In 2024, workers' compensation was the only insurance line showing premium decreases, driven by rate reductions that outpaced payroll growth. Despite this, workers' compensation remains one of the most profitable lines for underwriting in the property and casualty industry, with a combined ratio of 86% in 2024.

Progressive's Commercial Insurance Strengths [3]

Progressive has established itself as an innovation leader in the insurance industry, being:

The first auto insurance company to offer phone purchases (1993)
A pioneer in online policy purchases (1997)
An early adopter of mobile technology for policy management
The first to provide 24/7 claims reporting

The company operates in three main segments:

Personal lines
Commercial auto
Other indemnity

Business Owner's Policy (BOP) Coverage [1]

For comprehensive business protection, both companies offer Business Owner's Policies (BOP). Here's what you should know about BOPs:

A Business Owner's Policy (BOP) is specifically designed for small and medium-sized businesses, providing:

Cost-effective protection against common risks
Coverage for property damage
Protection against lawsuits
Income loss coverage for unexpected events
The policy bundles general liability and property insurance together, typically offering reduced premiums compared to separate policies.

However, it's important to note that a standard BOP typically does not include:

Commercial auto insurance
Workers' compensation
Health insurance
Disability insurance
Professional liability coverage

Making Your Decision [2]

When choosing between Progressive and Pie Insurance, consider these factors:

Premium costs: Business liability coverage premiums vary based on:
- Type of product or service you provide
- Perceived level of risk
- Your specific business type
Cost savings: Some insurers can secure workers' compensation coverage at lower costs than individual companies can obtain on their own through group negotiation power.

Visit our detailed guides for more information: [4]

Conclusion

The law provides workers' compensation as the sole remedy for an injured employee. Therefore, it's crucial to check with your state insurance department to understand the specific requirements for your business type.

Both Progressive and Pie Insurance offer valuable coverage options for small businesses, but your choice should ultimately depend on your specific business needs, industry requirements, and state regulations. Consider getting quotes from both providers and comparing their specific offerings for your situation [2].

Remember to review your coverage needs annually and adjust your policies as your business grows and evolves. The right insurance partner will not only provide necessary coverage but also help you manage risks and protect your business's future.