Sherri Haskell | Medicare Strategic Specialist

The Distinction

This Is Medicare Strategy.

There's a significant difference between someone who processes your Medicare paperwork and someone who investigates your entire situation — your income, your coverage history, your retirement timeline, your physicians, your prescriptions, your financial goals — and then finds the answer that most people never knew existed.

Sometimes that answer is a new plan. Sometimes it's the confidence of knowing you're already in exactly the right one. Either way, you'll know — and you'll know why.

I don't hand you a brochure. I ask the questions nobody else thinks to ask. And I don't stop until I've found the right answer for the right person.

That approach has uncovered hidden costs, avoided five-figure penalties, and given clients the clarity they didn't know they were missing.

That's where strategy changes everything.

Who I Work With

Two audiences.
One unwavering standard.

For Individuals Approaching Medicare & Solving Existing Issues

You're about to make decisions that will affect your healthcare access, your out-of-pocket costs, and your retirement finances for years to come. You deserve more than a sales pitch. You deserve a strategy.

For CPAs, CFPs, Attorneys & Financial Advisors

Medicare decisions don't happen in a vacuum. IRMAA thresholds, income timing, Roth conversions, RMDs — the intersections with your client's financial plan are numerous. I work alongside you so your clients get the complete picture — healthcare and financial, fully aligned.

Why It Matters

“The right answer often isn’t the obvious one. Sometimes it’s the one nobody thought to look for.”

One of my first clients came to me with a modest income and an enormous premium bill. She wasn’t looking for a new plan. She wanted to know why her premiums had suddenly skyrocketed. Something didn’t add up.

Because of my financial background, my instincts took me straight to the source — a situation that looked one way on the surface and was something else entirely underneath. I explained in plain English what exactly had happened and why. I mapped out an immediate solution and a roadmap for the future, in coordination with her wealth planner.

She left our conversation with a plan she didn’t know was possible.

That’s what Medicare strategy looks like.

Medicare documents on a desk with a sticky note reading Something doesn't add up

About Sherri

Clinical Background

Cardiovascular Critical Care Nurse Specialist — Top-10 Medical Center

Capital Markets

Stockbroker · Private Equity Partner · Registered Investment Advisor · Hedge Fund Manager

Track Record

$170M+ raised · 50+ companies advised · 3 securities licenses

Medicare

Licensed Insurance Broker · CA License #4496898 · Coast to Coast Health Insurance Solutions

Uniquely Suited.

Most people who work in Medicare come from insurance. I come from a cardiovascular ICU and a trading floor — and that changes everything about how I do this work.

I began my career as a Cardiovascular Critical Care Nurse Specialist at one of the top-ten medical centers in the country — six years at the bedside where the margin for error is zero and the stakes are always real. I learned early that the right decision, made at the right time, changes outcomes.

That instinct followed me into financial services. Over two decades in capital markets: Stockbroker, Private Equity Partner, Registered Investment Advisor, Hedge Fund Manager. Three securities licenses. $170M+ raised. Dozens of companies advised from inception to exit.

I don’t think or operate like a typical Medicare agent. I’m a broker. I explore. I investigate. I spend whatever time it takes to understand a client’s unique situation — and then I find the answer that most people never knew was available. Often, it’s an answer that wasn’t even on the table until I put it there.

Medicare is where clinical knowledge and financial consequences collide — and most people navigate it without either. I bring both.

Definition of Trust.

This photo was taken on the day Trina — a mare from a wild Colorado herd who had never seen water — trusted me enough to stand at the ocean’s edge. It took months to get there. It was worth every minute.

“One of the greatest lessons I’ve learned about trust didn’t come from a boardroom or a hospital. It came from earning the confidence of an Arabian mare who had never seen the ocean.”

My Discovery Process

I don’t start with a plan comparison. I start with questions — the kind that reveal what’s actually going on beneath the surface. Your income history. Your coverage timeline. Your physicians. Your prescriptions. Your retirement strategy. Your long-term financial goals. If you’re covered through an employer, a corporate plan, or a spouse’s benefits — that’s exactly where the investigation begins.

Schedule a Conversation

How I Work

Discovery

A conversation, not a sales pitch. I need your complete picture before making a single recommendation.

Investigation

I go deep — employer plans, existing coverage, and every financial intersection that matters.

Strategy

A clear, specific answer with the reasoning behind it. Not a menu of options — a strategy built for you.

Coordination

I work alongside your CPA, CFP, or financial advisor. I speak their language — fluently.

Ongoing Support

I stay in the picture — reviewing, adjusting, and alerting you when something changes.

For Financial Professionals

Your clients are making Medicare decisions.
Are those decisions aligned with their financial plan?

For high-income clients, Medicare isn’t just a healthcare decision — it’s a financial event. IRMAA surcharges, income timing around RMDs and Roth conversions, capital gains events — the intersections are numerous, consequential, and frequently overlooked.

1. Overlooking IRMAA Planning

The two-year lookback creates delayed premium impacts. Income events can trigger significant and unexpected surcharges that catch clients off guard.

2. Treating Medicare as a Commodity

Plan selection based on premium alone consistently leads to higher long-term costs and coverage gaps that affect quality of care.

3. Lack of Financial Integration

Decisions made outside the planning framework miss opportunities to optimize income structure, reduce tax exposure, and protect assets.

My Edge

I’m not a referral to another insurance agent. I’m a former RIA, stockbroker, private equity partner, and hedge fund manager with three securities licenses and a clinical background in critical care medicine. I speak your language — and your clients’ language — fluently.

I work alongside you, not around you.

Medicare done right helps protect everything else you’ve built for them.

When to Introduce a Medicare Conversation

Clients approaching 65 within the next 12 months
High-income clients subject to IRMAA thresholds
Retirement transitions
Income restructuring events
Clients evaluating existing or private coverage
Any client whose Medicare hasn’t been reviewed through a financial lens

Schedule a Conversation

Schedule Your Confidential Conversation

Healthcare decisions have financial consequences. Let’s make sure yours support the retirement you’ve worked so hard to build.

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Your information is always kept confidential and will never be shared.

Get in Touch Directly

(415) 404-7576

Sherri@c2csmarthealth.com

SherriHaskell.com

Sherri Haskell
Medicare Strategic Specialist
Coast to Coast Health Insurance Solutions, LLC
CA License #4496898

Medicare decisions have financial consequences.