Simply Business vs The Hartford: Which Is Better?
A marketplace that shops 20-plus carriers for the cheapest quote versus a 200-year-old A+ carrier that underwrites and pays the claim itself. Six rounds. Real numbers. One honest scorecard.
The verdict
The Hartford takes it, 5–1 on rounds.
The choice comes down to the size and complexity of your business — Simply Business for the smallest, budget-first operators, The Hartford once employees and claims accountability really matter.
Choose Simply Business if…
- • You're a sole proprietor or micro-business watching your budget
- • You want to compare 20+ carriers fast for the lowest first-year price
Choose The Hartford if…
- • You have employees and real workers' comp exposure
- • You want one accountable A+ carrier that owns your claim end-to-end
Round by round
- Round 1Carrier Structure: Marketplace vs Single Accountable InsurerThe Hartford winsSimply Business7/10
20+
Carriers Simply Business shops in one application
- Real price competition in one application
- Underwriting carrier changes per quote
Source: Simply Business marketplace model
The Hartford8/101 accountable carrier
Underwrites the policy and handles the claim itself
- One company owns the whole outcome
- Its own claims team and its own A+ rating, not a broker match
Source: The Hartford market position
So this round goes to Simply Business.
- Round 2Business Size FitThe Hartford winsSimply Business7/10
400+ trades
Specializes in sole proprietors and micro-businesses
- Purpose-built for the smallest operators
- 400+ niche trade types some carriers won't quote directly
Source: Simply Business market position
The Hartford8/101.3M+
Small businesses insured over 200+ years
- Built for larger SMBs with employees and premises
- 1.3M+ small businesses insured over 200+ years
Source: The Hartford market position
So this round goes to Simply Business for fitting the smallest operations better. It just knows your scale.
- Round 3Workers' Compensation StrengthThe Hartford winsSimply Business5/10
Partner-placed
Workers' comp available via carrier partners, not owned in-house
- Not a comp specialist — matches you to a partner
- Less reassuring when workers' comp is central to your risk
Source: Simply Business product lines
The Hartford9/10No. 3
U.S. News rank for workers' compensation; ~$81/mo under $300K payroll
- Full-service, in-house claims handling
- Averages ~$81/mo for payroll under $300,000
Source: U.S. News Best Small Business Insurance 2026
Round to The Hartford on that. Full-service claims handling beats being matched to partners every time.
- Round 4Financial Strength & Claims AccountabilityThe Hartford winsSimply Business6/10
No own AM Best rating
Places with A-rated partners including CNA, Travelers, Hiscox
- Backed by financially strong Travelers parent
- Accountability shifts with each quote's carrier
Source: Simply Business notable facts
The Hartford9/10A+ (Superior)
AM Best rating in The Hartford's own name
- Fewer complaints than expected for its size, 2022-2024
- Own rating, own name — no partner dependency
Source: AM Best ratings
This round goes to The Hartford.
- Round 5Renewal & Billing TrustThe Hartford winsSimply Business4/10
Recurring auto-renewal complaints
- Documented surprise renewal charges
- Service mixed across review sites
The Hartford7/10Consistent, praised claims handling
- Single carrier owns billing and claims end-to-end
- Less slick online experience than a digital MGA
So the round goes to The Hartford — not for price, but for trust.
- Round 6Price & All-In ValueSimply Business winsSimply Business8/10
~$97/mo
MoneyGeek 2026: among the most affordable providers studied
- Lowest first-year price for a micro-business
- Shopping carriers against each other keeps the price down
Source: MoneyGeek 2026
The Hartford5/10~$68-141/mo
GL ~$68/mo; BOP ~$141/mo ($1,687/yr); comp ~$81/mo
- Price includes claims depth and comp expertise
- Not the cheapest option available
Source: The Hartford pricing data
So this round goes to Simply Business.
Which one is for you?
Sole proprietor or freelancer wanting the cheapest liability policy
→ Simply Business · Shopping 20+ carriers lands a low first-year price fast
Owner of a niche trade carriers won't quote directly
→ Simply Business · 400+ business types placed across many partner carriers
Established business with employees needing real workers' comp
→ The Hartford · Top-3 U.S. comp writer with full-service in-house claims
Owner who wants one accountable A+ carrier behind every claim
→ The Hartford · Underwrites and handles claims itself, backed by its own A+ rating
Side 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
- An agent can structure coverage and catch gaps
- 200+ years, 1.3M+ small-business customers insured
- ~86% five-star on a Trustpilot business-insurance sample
- Fewer GL & commercial-property complaints than expected (2022-2024)
- 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
- Slower — most policies still finish with an agent
- One tier below biBERK's top A++ grade
- GL ~$68/mo, BOP ~$141/mo, workers' comp ~$81/mo
- Premiums vary further by trade, payroll, location and claims history