Best Small Business Insurance in Oregon

ERGO NEXT ranks first in Oregon at $93 monthly ($1,113 annually) because it solves the biggest bottleneck solo service providers face: getting instant certificates for client contracts and venue bookings without fees. Oregon businesses save on workers' comp and professional liability, making it ideal when you need affordable multi-policy coverage plus same-day proof.

ERGO NEXT costs $93 monthly in Oregon and ranks fifth overall, though delivering the state's cheapest workers' comp at $64 monthly, which matters since Oregon requires immediate coverage as soon as you hire your first employee. Professional liability costs $67 monthly (2nd cheapest), while ERGO NEXT's BOP runs $7 above Oregon's $137 average. If you need bundled liability and property protection, it's worth comparing rates from other providers.

ERGO NEXT ranks first nationally for digital experience and policy management because you can add additional insured endorsements, adjust coverage limits and download certificates through the app without calling an agent. Claims processing averages 15 days and live support runs weekdays only, though the 24/7 AI chatbot handles routine policy questions and certificate requests immediately.

ERGO NEXT offers equipment breakdown coverage through its BOP, protecting Oregon food service and retail businesses when HVAC systems, refrigeration or POS equipment fails and halts operations. Add cyber liability for data breach notification costs, tools and equipment coverage for contractor gear theft between job sites or hired and non-owned auto when employees use personal vehicles for client visits.

The Hartford ranks second overall in Oregon at $78 monthly ($933 annually) while having the cheapest rates for BOP, general liability and professional liability. With 215 years of experience and an A+ Superior rating, it works best for Oregon businesses prioritizing the lowest multi-policy rates and agent support over instant app-based certificate access for same-day client requests.

The Hartford costs $78 monthly in Oregon and ranks first for affordability because it offers the state's lowest rates across almost every major coverage type, helping you manage insurance costs when carrying multiple policies. BOP costs $104 monthly (saving $33), general liability costs $76 monthly (saving $20) and professional liability costs $66 monthly (saving $6).

The Hartford ranks first nationally for service quality, claims process and customer service, meaning faster claim resolutions and more responsive support when you need help after accidents or property damage. The tradeoff shows in digital experience, where it ranks last because you'll work with agents rather than downloading certificates instantly through an app like digital-first competitors offer.

The Hartford includes up to $25,000 employment practices liability insurance in its BOP at no extra cost, covering discrimination and wrongful termination claims from employees, job candidates and even vendors, which protects Oregon restaurants and retailers managing wage disputes with hourly workers. The Hartford's risk engineering team conducts on-site safety assessments to help prevent workplace injuries, reducing your workers' comp premiums over time.

Simply Business ranks 3rd in Oregon at $90 monthly ($1,081 annually) and first for coverage options because its 18-carrier marketplace includes specialty insurers for hard-to-place industries that single-carrier competitors often decline. It works best for Oregon businesses struggling to find coverage elsewhere or needing specialized policies like inland marine for mobile equipment and contract-required endorsements.

Simply Business costs $90 monthly in Oregon and ranks third for affordability, offering competitive rates for general liability at $89 monthly (saving $7) and BOP at $134 monthly (saving $3). Professional liability costs $71 monthly and workers' comp $67 monthly, both above Oregon's average, so explore other providers if these coverage types are your primary need.

Simply Business ranks fifth for customer service and eighth nationally for claims processing, meaning slower claim resolutions and less responsive support when you need help after accidents or losses. Its platform ranks third nationally for digital experience because you can compare carrier quotes, download certificates and manage policies online, though you'll work directly with whichever carrier underwrites your policy for actual service issues.

Simply Business participates in Amazon's Insurance Accelerator Program and serves Etsy sellers through partnerships with specialty carriers, making it Oregon's go-to option for e-commerce businesses needing platform-compliant coverage that traditional insurers often reject. The multi-carrier marketplace includes Hiscox for professional services, CNA for contractors and Markel for food operations, letting you compare coverage terms across insurers to match specific contract requirements.