Small business insurance,
compared the way it should be.

What is small business insurance?

Small business insurance protects companies from financial loss caused by lawsuits, property damage, employee injuries, and business interruptions. Most small businesses carry general liability, workers' compensation, and commercial property as core coverages, often bundled into a Business Owner's Policy (BOP). Required coverages vary by state, industry, and business structure. Pricing depends on revenue, payroll, claims history, and risk class.

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  Travelers Small Business

  Small businesses seeking the strongest combination of credit quality, coverage breadth, and at-market pricing on direct-bind paper — especially growing businesses that need D&O, EPLI, or commercial umbrella alongside primary liability; trades, contractors, and field-services businesses needing the full GL + WC + auto + umbrella package on A++ paper.

  • A++ (Superior) A.M. Best paper across the full ten-line product ladder — the only direct carrier in our coverage set combining the highest rating with the broadest ladder
  • At-market pricing per Insureon medians ($42 GL, $57 BOP, $45 WC) — neither cheapest nor premium, sitting at marketplace medians
  • NYSE-listed publicly-traded parent (TRV) with quarterly statutory-statement disclosure — primary-source financial transparency deeper than private direct-to-business peers
  • 172-year continuous operating history; one of the largest commercial claims organizations in U.S. P&C insurance; published workplace-safety research

  8.1/10

  Good

  Read review
• 

  Simply Business

  Small businesses whose profile could reasonably land on multiple panel carriers — especially buyers with mixed exposure (GL + PL + WC + cyber) where different panel carriers fit different lines — and who value broker-channel claims advocacy plus multi-carrier comparison pricing. Strong fit for micro-businesses in trades, services, professional services, and e-commerce outside Alaska and Hawaii.

  • Broad 8-carrier panel with all Excellent-band paper — Travelers (A++), Hiscox (A), Markel (A), Liberty Mutual (A), Accredited America (A), Cerity (A), Clear Blue (A), plus Harborway (Simply Business own-branded admitted program)
  • Travelers ownership provides operational stability and parent backing — $490M acquisition by NYSE-listed parent in August 2017
  • Honest pricing-disclosure methodology — "from $20.75/mo GL" explicitly defined as 10th-percentile quotes sold Jan–Jun 2025, not a teaser floor
  • Genuine claims-advocacy value-add — broker-of-record relationship pushes carrier for response in disputes, documentation, and resolution escalation

  8.1/10

  Good

  Read review
• 

  The Hartford

  Growing small businesses that need a single-carrier program across five or more commercial lines — especially those needing D&O, EPLI, commercial umbrella, native workers' comp, or commercial auto in the same placement; contractors, trades, and field-services businesses needing GL + WC + commercial auto + umbrella on one carrier; buyers who value 215-year claims-relationship depth over lowest premium.

  • Broadest direct-bind SMB product ladder in our coverage set — 10 commercial lines including D&O, EPLI, umbrella, native WC, and commercial auto
  • A+ (Superior) A.M. Best rating, upgraded from A in July 2025 — recent affirmation of underwriting and reserve discipline
  • 215-year continuous operating history; NYSE-listed publicly-traded parent (The Hartford Financial Services Group, HIG) with SEC-filed financials
  • Deep claims organization with phone and field-adjuster access beyond direct-to-business insurtech peers

  7.9/10

  Good

  Read review

• 

  Thimble review

  Gig workers, event-based micro-businesses (photographers, fitness instructors, weekend tradespeople, pop-up retailers), seasonal contractors, and early-stage side businesses whose actual liability exposure is intermittent rather than continuous — and whose state is not in the 14-state Thimble cyber unavailability list if cyber is a material need.

  Updated May 5, 2026
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  Pie Insurance review

  Small businesses whose primary insurance need is workers' compensation — restaurants, trades, light contracting, fitness studios, service businesses with hourly employees — especially those with variable headcount that benefits from pay-as-you-go payroll billing, and buyers who value instant AI-driven quote-to-bind over broker-channel WC placement.

  Updated May 5, 2026
• 

  Embroker review

  Venture-backed tech and SaaS companies, IT consulting firms, and professional-services firms in Embroker's named industry list that need D&O + EPLI + PL + cyber bundled with tech-specific underwriting depth — especially Series A to Series C startups scaling headcount and handling product-engineering liability, and accountants/lawyers/consultants placing PL on Everspan-backed programs added in October 2024.

  Updated May 5, 2026