Thimble vs The Hartford: Which Is Better?
One sells business insurance by the hour from an app. The other has been underwriting risk since 1810. Six rounds. Real numbers. One honest scorecard.
The verdict
Rounds split 3–3; The Hartford edges it on total score.
There's no universal winner — Thimble and The Hartford are built for opposite business rhythms, so match the carrier to how you actually operate, not which name feels safer.
Choose Thimble if…
- • You work in bursts — events, short jobs, solo gigs — and want to pay only for the days you're covered
- • You want the fastest possible quote-and-bind with no agent involved
Choose The Hartford if…
- • You have employees, vehicles, or year-round operations that need real workers' comp and bundled coverage
- • You want an A+ rated carrier's own balance sheet and low-complaint claims record behind you
Round by round
- Round 1On-Demand Flexibility & DurationThimble winsThimble9/10
1 hour
the shortest general-liability policy Thimble will sell
- Pay only for the exact window you're exposed
- Instant certificate of insurance on the spot
Source: Thimble on-demand product (dossier)
The Hartford4/10Annual only
The Hartford writes standard annual policies — no hourly or daily option
- Cheaper per day than stacked short-term policies for year-round operators
- No short-term option for one-day or one-off jobs
Source: The Hartford product model (dossier)
So this round goes to Thimble.
- Round 2Employees & Workers' CompThe Hartford winsThimble3/10
Comp only via partners, not core
- Not built for payroll risk
- No dedicated in-house comp claims team
The Hartford9/10"Handled our workers' comp claim quickly and professionally"
- No. 3 U.S. News rank for workers' comp
- Averages ~$81/mo for payroll under $300,000
Round to The Hartford on that. Their workers’ comp setup is just tighter and more reliable.
- Round 3Buying Experience & SpeedThimble winsThimble9/10
"Quick to get covered"
- Instant self-serve quote-and-bind, no phone call
- Share a certificate of insurance on demand
The Hartford6/10Agent-distributed
Primarily sold through independent agents and brokers, plus direct online quotes
- Human advice for complex bundles
- Slower than an instant app
Source: The Hartford distribution model (dossier)
So this round goes to Thimble.
- Round 4Coverage Breadth & Specialty LinesThe Hartford winsThimble4/10
GL, PL, BOP, equipment, events
Focused liability menu across ~130 professions — no auto, no in-house cyber or D&O
- Deep enough for ~130 professions with simple liability needs
- No commercial auto or in-house specialty lines
Source: Thimble product lines (dossier)
The Hartford9/10~$1,687/yr
Average BOP premium; also writes auto, cyber, D&O/EPLI and group benefits in-house
- One carrier, one claims process for multiple lines
- BOP bundles property and liability into one policy
Source: The Hartford pricing data (dossier)
So this round goes to The Hartford.
- Round 5Financial Strength & Claims Track RecordThe Hartford winsThimble4/10
"Claims processing could be better"
- No AM Best rating of its own
- Claims handled by whichever partner wrote the policy, not Thimble directly
The Hartford9/10A+ (Superior)
AM Best rating in its own name; fewer GL/property complaints than expected for its size, 2022-2024
- A+ Superior AM Best rating in its own name
- Fewer GL/property complaints than expected, 2022-2024
Source: AM Best / MoneyGeek complaint analysis (dossier)
This round goes to The Hartford.
- Round 6Price for How You Actually WorkThimble winsThimble8/10
from ~$17/mo
Advertised short-term GL starting price; ~$94/mo average across coverage types
- Short-term GL advertised from ~$17/mo
- No wasted premium for occasional work
Source: Thimble / MoneyGeek (dossier)
The Hartford6/10"Not the cheapest quote I got"
- Usually cheaper per day than stacked short-term policies for continuous work
- Rarely the cheapest quote at the entry point
So this round goes to Thimble for keeping your cash in your pocket.
Which one is for you?
Wedding photographer who needs one-day event liability a few times a year
→ Thimble · Thimble's by-the-day policy and instant certificate fit event work perfectly
Landscaping company with five employees, trucks and year-round operations
→ The Hartford · Payroll needs workers' comp and continuous operation favors The Hartford's annual bundle
Contractor with a growing payroll who needs serious workers' comp claims handling
→ The Hartford · Workers' comp is The Hartford's franchise strength, with full-service, low-complaint claims at scale
Solo consultant taking on a few short client projects a year
→ Thimble · On-demand professional liability covers the engagement without a year-round commitment
Side by side
- No premium wasted between jobs
- Instant certificate for a single hour, day, or event
- Deep enough for straightforward freelance risk across ~130 professions
- No agent required at any point
- 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)
- No cyber, EPLI, workers' comp or agribusiness lines
- Zero coverage for these specialized risks
- Not built for larger or more complex risk profiles
- Claims handled by the underwriting partner, not Thimble
- 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