Customer Experience & Why I Signed Up For Oscar Health Insurance - Sarah Doody
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Customer Experience

Customer Experience & Why I Decided To Sign Up For Oscar Health Insurance

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I grew up in Canada and trying to figure out the American health insurance system is something that’s been a huge challenge for me.

I remember getting my first “real” job at a big Fortune 500 software company and being emailed a ton of forms to fill out for health insurance. I had no idea what any of it meant. Unfortunately, there wasn’t really anyone who could guide me through the process.

No one in the human resources department wanted to be advise me because of that delicate line between “advising” and “choosing”. It was so very frustrating for me as I felt totally blind. If someone had asked me what my plan deductible was or what my yearly out of pocket maximum was, I would have been clueless.

It wasn’t because I didn’t have the brains to figure it out. It was because the process was so broken and the information was so inaccessible that I just gave up out of impatience and total frustration. Each plan had it’s own brochure or PDF with tiny fonts and crazy charts and tables filled with insurance and legal jargon.

Over the decade or so that I’ve been responsible for my own American health insurance, I feel like I finally have a better understanding of the key things to look for in plans. However, after having at least 6 different health insurance companies throughout 3 different jobs, I can attest to the fact that they are all broken.

All the information is hard to understand. All the communications are done in formats that are inaccessible and poorly designed. And each time I had to call a health insurance company with a question, I felt like they were reading answers crafted from their legal department rather that listening to me as a person and giving me a personal response.

The customer experience of health insurance company is awful. No wonder so many people don’t have health insurance or don’t understand the insurance they do have. I have a college degree and even I find myself questioning my coverage and wondering if I’m getting scammed.

A few years ago when the Affordable Care Act started to come to life, I wrote an article called EnrollUX 2013: Designing A Better Health Insurance Enrollment. The article talked about how the California HealthCare Foundation enlisted the help of IDEO to design a proposed new system to help guide millions of people through the process of signing up for health insurance.  I’m still wondering if anyone over at ever heard about this and how that whole rollout had the outcome that it did.

I’ve been searching for health insurance for about a year. I’ve been covered through a COBRA plan that I opted-into after leaving a startup I was previously at.

I looked into health insurance through the Freelancer’s Union, but I honestly had a really bad experience trying to sign up with them. Apparently they were completely swamped with requests when I was trying to sign up. But as a consumer I still felt a bit blind — I didn’t understand the forms I was filling out, I had trouble getting answers, and the entire process had a lot of friction in it.

So, I decided to stop my enrollment process and just keep paying my high COBRA premiums because I knew it would not expire until September 2014.

Over the last 6 months or so I’ve heard so much about Oscar health insurance. Finally, I decided to check them out and at least get a quote. I honestly hadn’t read any of the press they’d received, such as this New York Times article. And me only exposure to them had been through seeing a tweet every now and then from people.

The first time I went to the Oscar website site, I really felt like I could trust them. The site is very simple, easy to navigate, and uses language that normal people use. I didn’t feel like they were trying to cover their asses and put their best interest before mine.

Within about 3 minutes on the site, I was able to get a quote that was easy to understand because it was presented in a simple, elegant, well designed layout. From that point, I was able to identify the 3 plans that I knew fit my budget.

Next, I had to narrow down which plan made sense for me. Someone from Oscar emailed me and I was able to ask them some questions that I couldn’t find answers to such as whether or not the 3 plans covered things like acupuncture or physical therapy. I also wanted to double check the yearly out of pocket maximums with the Oscar representative. Even though they are clearly listed on the website, I just wanted to be 10,000% sure because that number is so important to me. God forbid anything bad happen to me, I didn’t want to be stuck with a $20,000 out of pocket maximum bill because I didn’t understand something in the plan. The Oscar representative assured me that I understood the out of pocket maximum correctly.

When I was ready to sign up, the Oscar representative called me and the entire process was complete in 11 minutes.

I tweeted this and a few people said that the whole “sign up on the phone” part turned them off. But, I completely disagree.

If Oscar had sent me forms that I had to fill out, it would have taken far longer than 11 minutes for me to fill out the information. Also, putting the burden of filling out the forms on me adds the risk that I do it incorrectly, or that I don’t have the right software to fill in the forms, or that I have to print the form and scan it back it and email or fax it to Oscar. I completely see why Oscar does sign up over the phone. As well, it allowed me to ask the representative any final last minute questions.

Health insurance isn’t something that anyone really gets excited about. But, I am so excited to have Oscar as my health insurance. I think they have nailed the customer experience so far and I really love their focus on helping me live a healthy life.

I feel like they really want to go the extra mile to encourage me and make sure that I don’t need their services in the first place. For example, they offer partial gym reimbursements as well as a doctor on call so you can ask questions and decide if you really need to schedule an appointment or go to the ER.

As far as cost, it ended up being cheaper than my COBRA coverage and has a lower deductible. I can also pay my bill by setting up automatic payments from my bank account. When I had COBRA I had to mail in a physical check and include a little paper “voucher” that they sent me. It was so inefficient and was so time consuming!

It is so great to see people reinvent such an important part of our lives. I’m really curious to see how Oscar health insurance grows in the coming months and years. It’s so refreshing to know that if I need their services I won’t run into any surprises and that they truly care about my health.

PS: My coverage doesn’t actually start until March 1, so I haven’t even received my insurance card yet (which I imagine will be a lot more useful and well designed than the hard to read and flimsy ones that other companies mail out).




Dear Twitter: Please Don’t Change Your Design, I Like You Just The Way You Are

  • Mike

    Problem with new health insurance is that you must do research on who accepts them. While I’m doing my research, the clinic I want to visit CityMD, does not take Oscar.

    • izzy

      Make sure to check this with Oscar, and NOT with the clinic. Iv’e had many providers tell me they do not accept oscar, when in fact they did. I even had one provider claiming they “do not accept obamacare” (whatever that means) and after 2 min on the phone with oscar they were surprise to learn they they do in fact accept ‘obamacare’

      • Thanks so much for the tips. After I did my research I felt like Oscar had great coverage in the New York City area. But like you said it’s good to double check, especially as Oscar is a new provider. I’m sure the people at the medical offices haven’t made “Oscar” a part of their daily office vocabulary, yet!

      • 8104012

        This is infuriating – I’ve been told this too, the clinic will actually use the term Obamacare and I ask them what that means. I ask if they are refering to the ACA because Obamacare is slang, bordering on still being a perjorative. But they reply that they are just reading from a script their company has laid out. Unbelievable.

    • Katie

      I checked with Oscar and two CityMD locations participate: 2465 Broadway, upper west side, and 315 West 57th St., Columbus Circle.

      • Thanks so much for taking the time to look that up Katie, very helpful!!

  • Izzy

    I got there card and new member kit already, and i can tell you it is nothing like you’ve ever seen before!

    • I’m so excited to get mine!!! I saw some photos the other day, excited to get mine. It’s all a part of the experience. I remember with my last plan I’d often accidentally throw out new cards they’d send for various reasons. The cards would be sent in a plainly marked envelopes and I thought it was junk mail!


    Oscar is part of Magnacare network. City MD takes Magnacare. You should be good.

    • Thanks so much for sharing!! Very good to know that we should ask about “Magnacare” if the office isn’t familiar with Oscar yet.


    Did you end up getting your Oscar package yet ?

  • Agreed that Oscar has great customer service. You can also download their ID card from their website in case you do lose the one sent in the mail. And for pics of the “kit” see my post here –

  • Terminator123

    Hi… Have you started using Oscar? How has you experience been so far ?

  • Meurglys13 .

    I really need to see a dr and all I’m getting from magnacare oscar is bs. I’ve been on the phone all day trying to find someone who actually accepts this insurance and all I’m getting is the run around. whether I go to the website or call and speak to a rep they keep directing me to drs who do not accept their coverage, this is a sick twisted joke. I work hard I pay my bills I try to treat people with courtesy and dignity and all I ever get from people is lies and bs and misery. I’m seriously done with NY, it’s just a rat race here with people who are increasingly selfish and overweening with their me me me ambitions and pretension. I’m done, done and done.

  • Just a quick update, I had to put Oscar Health to the test. Here’s my review of the “Talk To A Doctor” feature that’s available from Oscar:

  • BarbaraGordon

    I’ve had Oscar for a year now. Less than a month after I signed up with them last year, I underwent emergency surgery in the middle of the night. Oscar picked up all of the costs required under my plan and was generally great to work with. Definitely check on the website as to whether a provider is in the Oscar network because many of the physician office receptionists are not quite sure. Most big radiology groups take Oscar so that isn’t an issue.

    • Good tip Barbara! Given how new Oscar is, a lot of providers don’t recognize the name. But, I feel like they are becoming more well recognized. Sounds like you had a great experience with Oscar so far!! Be well!

  • Amy

    Thanks, Sarah. It’s 2 years later, and you helped me pick my insurance with this piece!