Simply Business vs Progressive Business Insurance: Which Is Better?
A marketplace that shops 20-plus carriers for liability versus the #1 commercial auto insurer in the country. Six rounds. Real numbers. One honest scorecard.
The verdict
Progressive takes it, 4–2 on rounds.
This one turns almost entirely on a single question — does your business run on vehicles — so answer that before you compare a single price.
Choose Simply Business if…
- • You have no business vehicles and just need liability shopped cheaply
- • You're a niche or non-vehicle trade that standard carriers won't quote directly
Choose Progressive if…
- • A truck, van or fleet is central to how your business earns money
- • You want one A+-rated carrier's own strength behind an expensive vehicle
Round by round
- Round 1Commercial Auto DominanceProgressive winsSimply Business4/10
Not a specialty
Commercial auto available via partner carriers, not Simply Business's focus
- No dedicated commercial-auto underwriting
- Not a fleet expert — no dedicated tooling for vehicles
Source: Simply Business product lines
Progressive9/10~13% share
$10.8B in commercial auto premiums — 2x the next-largest writer
- Deepest vehicle underwriting expertise in the market
- Contractor commercial auto averages ~$260/mo
Source: Progressive market position, 2025
This round goes to Progressive Commercial.
- Round 2Fit for Non-Vehicle Micro-BusinessesSimply Business winsSimply Business8/10
400+
Small-business types Simply Business will quote
- Specializes in the smallest, non-vehicle operators
- 400+ business types advertised, including trades some carriers won't write directly
Source: Simply Business footprint data
Progressive4/10Partner-written
BOP, GL, workers' comp largely written through partner carriers
- Less tailored for office-based micro-businesses
- Non-auto lines written through partner carriers, not in-house
Source: Progressive product lines
So this round goes to Simply Business.
- Round 3How You Shop: Marketplace vs Fleet AgentProgressive winsSimply Business6/10
20+
Carriers shopped in one application for liability quotes
- Fast liability price comparison
- 20+ carriers compared in a single application
Source: Simply Business marketplace model
Progressive7/10~$260/mo
Average contractor commercial-auto premium, plus a huge agent network
- Agents built for fleets and for-hire work
- One of the largest independent-agent networks in the country
Source: Progressive pricing data
So this round goes to Simply Business.
- Round 4Financial Strength & Complaint RecordProgressive winsSimply Business6/10
No own AM Best rating
Places with A-rated partners; backed by Travelers parent
- Backed by a financially strong Travelers parent
- Accountability shifts with each quote's carrier
Source: Simply Business notable facts
Progressive9/100.87
2024 NAIC complaint index — below the expected 1.0
- A+ rated in its own name
- 2024 NAIC complaint index of 0.87 — fewer complaints than expected
Source: NAIC Complaint Index 2024
Round to Progressive Commercial on that. Clear ratings and fewer complaints make a difference when money’s on the line.
- Round 5Renewal & Billing TrustProgressive winsSimply Business4/10
Recurring auto-renewal complaints
- Documented surprise renewal charges
- Broker doesn't fully control the carrier's billing
Progressive8/10Easy to manage online, fleet-friendly
- Consistent, in-house billing and renewals
- Below-average complaint volume backs up the consistency
This round goes to Progressive Commercial.
- Round 6Price for the Risk You're Actually InsuringSimply Business winsSimply Business8/10
~$97/mo
MoneyGeek 2026: among the most affordable providers studied
- Lowest price for simple, non-vehicle liability
- ~$97/mo by shopping carriers against each other
Source: MoneyGeek 2026
Progressive5/10~$260-926/mo
Contractor auto ~$260/mo; for-hire trucking up to ~$926/mo
- Real vehicle coverage a liability marketplace can't match
- Not competing on price with pure liability policies
Source: Progressive pricing data
So this round goes to Simply Business.
Which one is for you?
Delivery driver, contractor or fleet owner
→ Progressive · Progressive is the #1 US commercial auto insurer by a wide margin
Owner-operator trucker or for-hire transport business
→ Progressive · Core underwriting strength as the commercial auto category leader
Sole-proprietor consultant with no vehicles
→ Simply Business · Marketplace shops competing liability quotes for non-vehicle operations
Home-based micro-business wanting the cheapest liability
→ Simply Business · Among the most affordable providers for the smallest operators
ProgressiveSide by side
- One application compares many insurers' prices at once
- Partners with A-rated carriers like Travelers and CNA
- Cheap, easy initial purchase
- Multi-carrier shopping can surface a lower quote for niche risks
- Undisputed market leader in commercial auto
- Deep underwriting expertise across contractors, for-hire and trucking
- Still offers easy bundling through its large agent network
- Direct underwriting tuned to every vehicle class
- Final carrier and premium vary by which partner you're matched with
- Claims experience depends entirely on which partner you're matched with
- Recurring reports of auto-renewal at higher prices with little notice
- Final premium depends on which partner carrier is matched
- Service and claims vary by which partner carrier is assigned
- Heavier process than a pure self-serve app
- Rates climbing industry-wide
- BOP, GL, workers' comp and cyber placed through partner carriers