A Medicare Advisor Who Works for You — Not the Carriers
I built Red Sky Insurance Advisors on one idea: that people navigating Medicare deserve honest guidance from someone who has nothing to gain by steering them toward the wrong plan.
From IT to Insurance — and Why That Pivot Matters
Before I became a licensed insurance advisor, I spent years in information technology. I was trained to solve problems methodically, to ask the right questions before recommending a solution, and to explain complicated systems in plain language. When I made the move into insurance in 2017, I brought all of that with me.
I didn't stumble into this work. I chose it because I kept watching people around me get lost in Medicare's complexity — confused by jargon, misled by mailers, and left without a real advocate after enrollment. I wanted to be the person who fixes that.
Since then, I've helped hundreds of Wisconsin residents find coverage that actually fits their lives. And I show up every year to make sure it still does.
What "Independent" Actually Means for You
Most people don't realize that not all insurance agents work the same way. Some are captive — they represent one carrier and can only sell that carrier's products. I'm not.
As an independent broker, I hold contracts with 13 to 14 insurance organizations and, depending on where you live, can compare anywhere from zero to 51 products to find what fits your situation. I'm not rewarded for recommending one plan over another. My compensation from carriers is fixed by law, regardless of which plan you choose — so my only incentive is to get it right for you.
That same law also prohibits me from charging you a consultation fee. My help costs you nothing. Your premium is identical whether you work with me or go directly to a carrier — you just get an informed second set of eyes at no added cost.
Licensed independent broker since 2017
Contracts with 13–14 insurance organizations
0–51 plan options depending on your location and situation
Legally prohibited from charging consultation fees
Compensation is carrier-fixed — no incentive to favor any plan
Certified Every Year — Because Medicare Changes Every Year
Medicare isn't static. Plans change. Formularies shift. Premiums move. What worked for you last year may not be the best fit this year.
I complete more than 100 hours of annual Medicare certification through AHIP — America's Health Insurance Plans — plus carrier-specific training on top of that. I do this every year, without exception, so that when you call me with a question, I'm current.
That ongoing training is also why I offer annual plan reviews to every client as a standing part of my service. Before each Annual Enrollment Period, I reach out to review your coverage, check for plan changes, and make sure nothing has shifted in a way that costs you money or limits your care. I don't disappear after enrollment.
Licensed Across Six States — So You Can Take Me With You
Many of my clients are Wisconsin residents today, but life doesn't always stay in one place. Retirement brings relocations, and the last thing you should have to do is start over with a new agent in a new state.
I'm currently licensed in Wisconsin, Minnesota, Illinois, Texas, Arizona, and Washington — and I'm adding states as my clients' needs grow. If you're moving from Wisconsin to one of those states, I can continue serving you without any gap in support.
If you're already working with me and considering a move, reach out before you go. There's a good chance I'm already licensed where you're headed.
How We Can Work Together
I meet clients the way that works best for them. That means:
In-person appointments at my seasonal Fitchburg coworking office
Kitchen-table visits for clients who prefer to meet at home
Phone consultations for straightforward questions and reviews
Virtual meetings via video for clients anywhere in my licensed states
Whether you're turning 65 and trying to understand Medicare for the first time, reviewing a plan that no longer feels right, or relocating and need to sort out your coverage in a new state, the first conversation is always free and always without pressure.
Frequently Asked Questions About Working With Me
How is Ryan compensated if consultations are free?
Insurance carriers pay licensed brokers a fixed commission rate that is set by law. That rate is identical regardless of which plan you choose, which means I have no financial reason to recommend one plan over another. You pay the same premium you would going directly to the carrier — I'm simply an additional resource at no added cost to you.
What does an annual plan review include?
Before each Annual Enrollment Period, I contact every client to review their current coverage. We look at any plan changes, premium adjustments, formulary updates, and whether your doctors and prescriptions are still covered. If a better option exists, I'll tell you. If your current plan is still the right fit, I'll confirm that too.
Who is Ryan Olson and what is Red Sky Insurance Advisors?
I'm Ryan Olson, a licensed independent Medicare broker based in Fitchburg, WI. Red Sky Insurance Advisors is my independent agency, founded in 2017. I specialize in Medicare and individual health insurance, serving clients in Fitchburg, Madison, and across Dane County, as well as clients in my other licensed states.
Can I keep working with Ryan if I move out of Wisconsin?
Possibly, yes. I'm currently licensed in Wisconsin, Minnesota, Illinois, Texas, Arizona, and Washington. If you're relocating to one of those states, we can continue working together without interruption. I'd encourage you to reach out before your move so we can plan ahead.
Is Ryan Olson certified to sell Medicare plans?
Yes. I complete annual certification through AHIP — America's Health Insurance Plans — along with carrier-specific training each year. This ongoing certification is required to sell Medicare Advantage and Part D plans and ensures I'm current on plan options, regulatory changes, and enrollment rules every year.
*Disclaimer:
Red Sky Insurance Advisors is an independent insurance agency. Ryan Olson is licensed to sell insurance products in Wisconsin, Minnesota, Illinois, Texas, Arizona, and Washington. Product availability varies by state and county. The number of available plans (0–51) depends on your location and coverage type. Ryan Olson is compensated by insurance carriers at a fixed rate established by the Centers for Medicare & Medicaid Services (CMS). Carrier compensation does not vary based on plan selected. Consultations are provided at no cost to the consumer. Red Sky Insurance Advisors is not affiliated with or endorsed by the federal Medicare program or any government agency.*
