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Your Trusted Insurance Partner in Alameda, CA
Caffrey Insurance is a family-founded employee benefits brokerage firm dedicated to providing tailored insurance expertise for small businesses (1-100 employees) and individuals. Founded by Lynn Caffrey, an industry veteran with decades of experience, we specialize in small business health insurance and have expanded to serve individual and senior markets. Our approach combines deep industry knowledge with personalized service, offering access to hundreds of health plans, dental, vision, life, and ancillary coverage.

We prioritize client needs by conducting thorough research, presenting alternatives, and facilitating seamless enrollment and ongoing support. Our value-added services include custom enrollment portals, HR resources, and transparent guidance to help clients navigate complex insurance landscapes. With a focus on the San Francisco Bay Area, we serve California businesses and individuals, emphasizing trust, clarity, and long-term partnerships.
Services
Health Insurance Medicare Plans Small Business Insurance Dental Insurance Vision Insurance Life Insurance Disability Insurance Travel Insurance Ancillary Coverage Senior Insurance
Highlights and features
  • We offer free broker services with no additional costs to consumers
  • Our team has decades of experience navigating ACA regulations
  • We provide personalized claims assistance and HR resource access
  • We specialize in California-specific insurance solutions
  • We maintain strong carrier relationships for better plan options
What people say
Super helpful Efficient, care, honesty Best insurance broker Trust implicitly Compassionate guidance
Services
Health Insurance
We provide comprehensive health insurance solutions for individuals, families, and small businesses. Our services include plan comparison, ACA compliance guidance, and enrollment assistance. We help clients navigate deductibles, copays, and out-of-pocket maximums while ensuring access to in-network providers. Our expertise covers both marketplace and private plans with no broker fees.
Medicare Plans
Our Medicare specialists assist with Part A/B enrollment, Supplement (Medigap) plans, Advantage plans, and Prescription Drug Plans (PDP). We explain coverage differences, help avoid penalties, and provide annual plan optimization during open enrollment periods. We clarify 'donut hole' complexities and network limitations for California seniors.
Small Business Insurance
We help businesses with 2-100 employees establish compliant group health plans. Services include carrier comparison, HR portal implementation, and ACA reporting assistance. We explain employer contribution requirements, network limitations, and alternative options like QSEHRAs for small businesses seeking cost-effective solutions.
Dental Insurance
We offer standalone dental coverage for individuals and group dental plans for businesses. Our solutions include preventive care, major procedures, and discount plans. We help clients understand waiting periods, annual maximums, and network dentist availability across California.
Travel Insurance
We provide temporary insurance solutions for travelers and individuals needing gap coverage. Our plans cover emergency medical expenses, trip cancellations, and unexpected delays. We explain policy limitations, claim submission processes, and coverage exclusions for pre-existing conditions.
People
Lynn Caffrey
Founder
With over 40 years of insurance experience, Lynn Caffrey established the company to help individuals and small businesses navigate complex insurance markets. Her expertise spans ACA compliance, senior insurance, and group benefits, with a focus on personalized solutions for California clients.
Gabriel Caffrey
President
As President, Gabriel Caffrey leads client services and strategic growth. He specializes in small business insurance solutions and has expanded the company's digital tools for improved client access to enrollment portals and HR resources.
Questions
What qualifies as a small business group plan?
A group requires at least 2 employees, with one W-2 employee unrelated to business owners. Partner-only businesses no longer qualify under ACA regulations.
Can I get insurance outside open enrollment?
Qualifying life events like job loss, income changes, or moving allow enrollment outside standard periods. Documentation verification is required for eligibility.
How do Medicare Supplement plans work?
Medigap plans cover costs not paid by Original Medicare. Plan F offers comprehensive coverage, while High-Deductible options reduce premiums. California allows annual birthday-based plan changes.
Are pre-existing conditions covered?
Under ACA regulations, all plans accept applicants regardless of health status. Rates cannot be adjusted based on pre-existing conditions in individual and group markets.
What HR tools do you provide?
We offer custom enrollment portals, compliance documentation templates, and access to low-cost HR resources to streamline benefits administration for small businesses.