As you say, the sheer number of choices can be overwhelming. This is why we have our brokers, who are experts on the nuances of health plans, recommend a few plans for each employee - we do the shopping for most employees, and the power users can pick for themselves if they like. Employees can always chat with us in-app as well.

If you work for a large employer, you have benefits professionals who spend all year thinking about this - we work with small employers who don't have these kinds of resources and are happy to offload it onto us.

That isn’t a benefit at all. Not to mention I don’t see why an employer has any less incentive to offer a plan that “screws you”.

Anyone can easily use healthcare.gov to find a plan appropriate to their needs. And you’re healthcare providers are not tied to your employer, in case you leave your job.

And any employer that doesn’t offer HSAs is really screwing their employees by not giving the option of the best investment vehicle available to Americans.

An additional benefit is your compensation gets more transparent, as you can easily see the dollar amount of the benefits you’re receiving prior to accepting job offer.

One of the key disadvantages is that you don't get to shop for health insurance, too. This becomes obvious when you change jobs/get bought out and suddenly your dentist or pediatrician isn't covered.