Progressive vs Simply Business Reviews: A Comprehensive Comparison for Small Business Owners

Choosing the right insurance provider is one of the most critical decisions you'll make as a small-business owner.

For the more than half million U.S. entrepreneurs who start a business each month, making the right insurance moves can mean the difference between a first-anniversary celebration and an inaugural-year flop.

Two names that frequently appear in small business insurance searches are Progressive and Simply Business, but these companies operate in fundamentally different ways. This comprehensive review will help you understand which option might be the best fit for your business needs [1].

Understanding the Key Difference: Carrier vs. Broker

Before diving into detailed reviews, it's essential to understand that Progressive and Simply Business aren't direct competitors—they operate under entirely different business models.

Progressive is an American insurance company that is currently the #2 auto insurer in the United States behind State Farm, co-founded in 1937 by Jack Green and Joseph M. Lewis, and is headquartered in Mayfield, Ohio.

The company ranked #62 on the 2024 Fortune 500 list of the top American corporations.

When you purchase insurance from Progressive, you're buying directly from the carrier that underwrites your policy and pays your claims [2].

Simply Business is a digital broker and agency for small business insurance.

In August 2017, The Travelers Companies acquired the company from Aquiline Capital Partners for approximately $490 million.

Rather than underwriting policies themselves, Simply Business connects small businesses with multiple insurance carriers, comparing quotes from various providers to find competitive rates. When you get a quote through Simply Business, you might actually end up with a policy underwritten by Progressive, Travelers, or another carrier in their network [3].

This fundamental difference affects not just pricing, but also your shopping experience, the range of options available, and how you'll interact with your insurance provider throughout the policy lifecycle.

Progressive Commercial Insurance: Detailed Review

Company Background and Financial Strength

Progressive operates in three segments: personal lines, commercial auto, and other indemnity, with the personal lines segment writing insurance for private passenger automobiles, motorcycles, boats, and recreational vehicles through both an independent agency channel and a direct channel.

The company's financial stability is substantial, providing peace of mind that they can pay claims even during economic downturns or after major catastrophic events [2].

Coverage Options

Progressive's commercial insurance offerings focus primarily on specific business needs:

Commercial Auto Insurance: This is where Progressive truly excels.

Progressive is the second-largest auto insurer in the United States as of the 2023 fiscal year, with 15.2% of the market.

Their commercial auto segment is particularly robust, offering coverage for various vehicle types including trucks, vans, and specialty vehicles [4].

Commercial auto insurance policies typically have higher liability limits, for example $1 million, and may have provisions that cover rented and other non-owned vehicles, including employees' cars driven for company business.

Business Owners Policy (BOP): [5]

A business owner's policy is a "package" product that typically includes property, business interruption/continuation and liability insurance, and for many small businesses, purchasing a BOP can be a less costly option than buying individual policies.

Progressive offers BOP coverage, though their offerings are more streamlined compared to some competitors who specialize in comprehensive commercial packages [1].

Professional Liability: Progressive's professional liability offerings are more limited, typically available through partnerships rather than direct underwriting. The other-indemnity segment provides professional liability insurance primarily to community banks, including directors and officers liability insurance.

Digital Experience and Technology

Progressive claims being the first auto insurance company to allow customers to purchase insurance policies over the phone in 1993, and to have a website in 1995, and have policies available for purchase online in 1997, later enabling customers to use mobile browsers and smartphone apps for rating and managing policies, and reports to be the first to offer 24/7 claims reporting.

Their online platform allows businesses to obtain quotes, purchase policies, manage coverage, file claims, and access policy documents entirely online. This streamlined digital experience can save considerable time for busy business owners who prefer minimal interaction with agents [2].

Pricing and Value

Generally, Progressive tends to be more competitive on commercial auto insurance due to their specialization and scale in that market. Their technology-driven underwriting can result in faster quotes and potentially lower rates for lower-risk businesses. For businesses with significant vehicle fleets or transportation needs, Progressive often provides excellent value.

However, for businesses needing comprehensive coverage packages beyond commercial auto, Progressive's pricing may not always be the most competitive option.

Best Suited For

Progressive is an excellent choice for:

Transportation and logistics companies
Delivery services
Businesses with significant vehicle fleets
Very small businesses (1-10 employees) seeking straightforward coverage
Tech-savvy business owners who prefer digital-first interactions

Simply Business: Detailed Review

Company Background and Business Model

Simply Business was launched in 2005 as an online broker for business insurance and the trading name of Xbridge.

Simply Business launched their first office in the United States in December 2016.

As a digital broker now owned by Travelers, Simply Business has access to multiple carrier relationships, allowing them to shop your business across various insurers [3].

How Simply Business Works

As a broker, Simply Business doesn't underwrite policies themselves. Instead, they:

Collect information about your business and coverage needs
Compare quotes from multiple insurance carriers in their network
Present you with options from different providers
Help facilitate the purchase process
Provide ongoing support for policy management

This means you're essentially getting the benefit of shopping multiple carriers through a single platform, potentially saving time while accessing competitive rates.

Coverage Options

Because Simply Business works with multiple carriers, they can typically offer a broader range of coverage options than any single carrier:

General liability insurance
Business owners policies (BOP)
Professional liability/errors and omissions
Commercial property insurance
Workers' compensation
Cyber liability insurance
Commercial auto (through carrier partners like Progressive)

In 2021, Simply Business was selected to participate in the Amazon Insurance Accelerator Program to distribute general liability coverage to Amazon sellers.

This partnership demonstrates their focus on serving specific business niches with tailored solutions [3].

The Broker Advantage

Working with Simply Business offers several potential advantages:

Multiple Options: Rather than being limited to one carrier's appetite and pricing, you can compare multiple options. If Progressive doesn't want to write your particular business type, Simply Business can present alternatives.

Expert Guidance: Brokers can provide valuable advice on coverage adequacy and help you understand policy differences that might not be apparent when shopping directly.

Ongoing Advocacy: If you have a claim dispute or coverage question, a broker can advocate on your behalf with the carrier.

Potential Considerations

Additional Layer: Some business owners prefer dealing directly with their insurance carrier rather than having a broker as an intermediary.

Carrier Limitations: You're limited to the carriers in Simply Business's network. If a particular carrier you want to work with isn't in their network, you'd need to go direct.

Commission Structure: Brokers earn commissions from carriers, which is built into your premium. However, this doesn't necessarily mean you'll pay more—brokers often have access to competitive rates due to their volume.

Best Suited For

Simply Business works well for:

Business owners who want to compare multiple carriers efficiently
Companies needing specialized or hard-to-place coverage
Businesses that value having an advisor to guide coverage decisions
Amazon sellers and e-commerce businesses
First-time business owners navigating insurance for the first time

Key Factors to Consider When Choosing

Your Business Type and Industry

In a survey by the National Federation of Independent Business (NF

Progressive vs Simply Business Reviews: A Comprehensive Comparison for Small Business Owners

Understanding the Key Difference: Carrier vs. Broker

Progressive Commercial Insurance: Detailed Review

Company Background and Financial Strength

Coverage Options

Digital Experience and Technology

Pricing and Value

Best Suited For

Simply Business: Detailed Review

Company Background and Business Model

How Simply Business Works

Coverage Options

The Broker Advantage

Potential Considerations

Best Suited For

Key Factors to Consider When Choosing

Your Business Type and Industry

Sources