• Clear and Creative Health Insurance Solutions

  • Your Guide through the Benefits Labyrinth

  • Helping You Make Friends with Your Benefits


We specialize in helping individuals and groups find health insurance along with a wide range of additional benefits. We’ll simplify the process so you are confident in your decision and satisfied with the results.

We Serve

Individuals and Families

We help individuals and families meet the tax mandate to get covered while balancing options and finding the best solution for your needs and budget.

Small Groups / Business

We help provide you and your employees with the best benefits program.


Medicare prescription drug, advantage and supplement carriers can be very confusing. We'll explain it clearly and help you make your decision.

What Our Customers Say

"Lynn was a fount of information, super helpful and steered me in the right direction. [I] feel so lucky to have met Lynn and trust her implicitly…I could see that she only had my best interests at heart.”


"You are different from any image I have had of an insurance broker. I simply enjoy being with you. I experience a combination of efficiency, care, honesty, commitment and flexibility. I couldn't ask for better."

Miki Kashtan, Bay Area Nonviolent Communication

"I'm glad there are individuals like Gabriel who can break it down so the average joe can understand the ins and outs of each plan, and make better-informed decisions."


The Caffrey Insurance Solutions Promise

  • Listen to you 
  • Research plans
  • Present alternatives

You choose the best way to make use of our expertise. And of course, our services are free to you. We work with clients of all ages and backgrounds, and group sizes from 2-100 employees. We provide access to value added services such as custom enrollment portals, HR resources and referrals upon request.

  • Answer your questions
  • Expedite your enrollment
  • Keep your plans running smoothly

We love to work with start-up companies and help you get your employee benefits programs on the right track.

We work throughout California but concentrate our services in the San Francisco Bay Area and are happy to visit you at your location. 

Frequently Asked Questions

Groups & Businesses

A group is defined as at least 2 people, at least one of whom is paid on a W-2 basis and who is not related by marriage to any owner of the business. Partner-only businesses are no longer eligible for group plans under the Affordable Care Act.

Generally you need to provide documentation of the legitimacy of your business and sufficient payroll history to show you've been around at least a short while. The types of documents usually include a business license, proof that you are registered with the California Secretary of State's office, a Statement of Information listing business owners and address, and any DBA (Doing Business As) paperwork if applicable.

For payroll purposes, most insurance carriers will insist on a copy of the latest DE-9C Quarterly Contribution Return and Report of Wages form showing that at least one full time employee has been active for at least half of the prior calendar quarter. However, some carriers will accept less payroll, especially if you are a newly incorporated startup. If you have questions as to whether a group plan is a viable option, please contact us.

In some instances, a group plan will not consider an individual or family plan a qualifying reason to waive coverage. We can help you sort out the factors in play and find the right solution.

Except in one particular circumstance, you cannot. This is specifically prohibited under the ACA and carries stiff tax penalties of up to $36,500 per year per employee if you are shown to be reimbursing for open market plans.

There is a particular type of Health Reimbursement Arrangement (HRA) that small businesses can set up to allow partial reimbursement for purchase of plans on the individual market. This <strong>Qualified Small Employer Health Reimbursement Arrangement (QSEHRA) must be done instead of a standard group plan and has far fewer protections for employers and employees. These arrangements do not have access to group plan networks, have no provisions for enrolling employees in coverage if they have missed the standard open enrollment period.

If you are a small group between 1-50 employees, you are not required to put a plan in place. However, the plan options available for groups are substantially more comprehensive than those available on the individual and family market.

Individuals & Families

Nothing. A broker's services are always free to the consumer. We are paid by the insurance vendors, and it is a large part of our job to service your account and help resolve any issues that may arise.

Coverage can be provided by an employer or purchased on the open market. There is a narrow window each year to sign up for coverage, and it is not generally possible to get coverage outside that time frame unless there is a qualifying event. The next open enrollment period for coverage starting in January of 2016 runs from November 1st 2015 to January 31st 2016.

There are a wide variety of Qualifying Life Events that could permit you to buy coverage on the open market or through Covered California. Generally speaking you may qualify for any involuntary loss of coverage, significant income change, getting too old to stay on a parent's plan, changing residency or marital status, having a child, acquiring citizenship, and many others. Covered California provides a useful reference for the types of qualifying events.

No. Under the Affordable Care Act, there are no health questions asked and no effect on rates if you have a condition.

It varies depending on the plan. Similar to your insurance, a deductible is the amount you pay in full up front before the insurance company steps in and pays the lion's share of the costs. However, there are some services that you pay for on a strict copayment structure that you do not need to meet the deductible for. These include almost all basic medical visits.


You are eligible as soon as you turn 65. However, if you are still working and your company provides benefits, you can delay signing up until you are ready to leave the company. If your company has under 20 employees, let us explain.

4 months prior to the month of your birth, you can go to Medicare.gov and apply online for Medicare. If you are already receiving Social Security, a Medicare card will be sent to you automatically. If the card shows Part A and Part B and you don't want Part B yet, you'll need to fix this with the Social Security Department.

Part A is free. Part B for 2015 has a base cost of $104.90 per month. This is based on an adjusted gross income of $85,000 for an individual and $170,000 for a family. If your income is higher, the cost will be higher. Here's the link for higher incomes. Part D is a separate product for prescription drug coverage, and the government cost for Part D is free but it can cost if you are a higher earner.

Medicare definitely does not pay for everything, and it is a good idea to buy a Medicare Supplement (Medigap) or a Medicare Advantage plan to augment Medicare.

Advantage plans are typically HMO-type programs where you select a primary care physician and are referred to specialists and hospitals by that physician. Kaiser Senior Advantage is the primary example of this that most people know about.

A Supplement plan allows you to any provider nationwide as long as they accept Medicare patients. A Plan F is the most comprehensive Supplemental plan and covers 100% of what Medicare Part A and Part B do not cover for any claims that are a Medicare-permitted expense. There are other options to reduce costs.

We help individuals and families get clear advice and coverage for the affordable care act. Get in touch with us today.