A Referral Partner of 40 Quarter Coach
Credentialed expertise in Social Security claiming strategies, Medicare coordination, and retirement income planning — serving pre-retirees across the Sacramento region and Northern California.
Cassandra Barry is a Managing Director and Partner at Arrowroot Family Office in El Dorado Hills, California — a wealth management firm serving high-net-worth individuals and families across Northern California and beyond. With a professional foundation spanning more than a decade in financial services, Cassandra has built her practice around one core conviction: that retirement planning is most powerful when every piece — Social Security, Medicare, investments, insurance, and legacy — is understood together.
As a credentialed Registered Social Security Analyst (RSSA®), Cassandra brings a level of rigor to Social Security planning that goes well beyond the guidance most pre-retirees receive. She understands that the decision of when and how to claim Social Security is one of the most consequential financial choices a person will make — and that getting it wrong can mean leaving tens of thousands of dollars on the table over the course of a retirement.
Before joining Arrowroot Family Office, Cassandra spent nearly a decade at Lagunitas Asset Management in Folsom, CA, where she served as CEO and Head of Financial Legacy Planning, leading the firm's insurance services division with a particular emphasis on Medicare, life insurance, and long-term care. That experience gave her both a deep fluency in the insurance landscape and a clear-eyed understanding of how Medicare fits into a broader retirement income picture — skills she now applies in partnership with 40 Quarter Coach to help Sacramento-area clients navigate the full complexity of their retirement transition.
Cassandra's approach: She believes in listening first — understanding each client's family situation, income sources, health profile, and long-term goals before any recommendation is made. Her philosophy is that custom solutions come from deep conversations, not pre-packaged plans.
Today, through her referral partnership with 40 Quarter Coach, Cassandra makes her Social Security and Medicare expertise available to pre-retirees across the Sacramento region — including El Dorado Hills, Folsom, Roseville, Granite Bay, Rocklin, Lincoln, and the greater Sacramento area — through a structured, fee-for-service consulting process designed around the client's best interest.
The Registered Social Security Analyst (RSSA®) designation is awarded by the National Association of Registered Social Security Analysts (NARSSA) to financial professionals who have demonstrated advanced, applied knowledge of Social Security law, regulations, and claiming strategies. It is a rigorous, specialized credential — not a general financial certification — and it exists specifically to address the gap between the complexity of Social Security rules and the quality of guidance most Americans actually receive.
Earning the RSSA® requires completing a comprehensive five-module self-study curriculum covering everything from basic benefit calculations to advanced coordination strategies for married couples, divorced spouses, survivors, and public-sector workers subject to WEP and GPO rules. Candidates must pass a proctored four-hour competency exam — including live case analysis using the RSSA Roadmap® software — before the credential is awarded. Ongoing continuing education and NARSSA membership are required to maintain it.
The RSSA® curriculum is built around real-world Social Security decisions — not theoretical financial planning. Core competency areas include:
The RSSA® credential remains relatively rare, particularly in the Sacramento region and Northern California. While general financial advisors may touch on Social Security in the course of broader planning, few carry a credential dedicated exclusively to it. For pre-retirees making one of the most permanent and high-stakes financial decisions of their lives, that specialization matters.
Through the partnership between Cassandra Barry and 40 Quarter Coach, pre-retirees in El Dorado Hills, Folsom, Sacramento, and across Northern California have access to a coordinated consulting process that addresses the full range of Social Security and Medicare decisions. All services are provided on a fee-for-service basis — meaning the only agenda is yours.
Personalized analysis using the RSSA Roadmap® software to identify your optimal claiming age — whether you're single, married, divorced, or widowed. Includes full earnings record review, benefit projections, and a written action plan.
For married couples, coordinating when each spouse claims can add substantially to your combined lifetime benefits. Cassandra models multiple claiming sequences to find the strategy that works best for your household — including survivor benefit planning.
Understanding when and how to enroll in Medicare — including Parts A, B, C, and D — is critical to avoiding costly late-enrollment penalties. This service helps El Dorado Hills and Sacramento-area clients navigate enrollment windows, coverage types, and how Medicare interacts with any existing employer or retiree coverage.
IRMAA surcharges can significantly increase Medicare Part B and Part D premiums for higher-income retirees. Cassandra's financial planning background makes her particularly well-positioned to help Northern California clients understand how their income — including IRA distributions, Roth conversions, and capital gains — affects their Medicare costs.
Should you claim at 62, at your Full Retirement Age, or wait until 70? The answer depends on your health, income sources, spousal situation, and risk tolerance. Cassandra walks through a break-even analysis that makes these trade-offs concrete and actionable — not theoretical.
California public school teachers, state employees, and other government workers in the Sacramento region may see their Social Security benefits reduced by the Windfall Elimination Provision or Government Pension Offset. Cassandra's RSSA® training covers both provisions in depth, ensuring affected clients have an accurate picture before they make any decisions.
Cassandra Barry and 40 Quarter Coach serve pre-retirees throughout the greater Sacramento region. Whether you live in El Dorado Hills, commute to Sacramento, or are based anywhere across the Northern California foothills, the consultation process is designed to work around your schedule — with in-person meetings available in El Dorado Hills and virtual sessions available for clients across the state.
The Sacramento region has a large and growing population of pre-retirees — many of them long-time state government employees, educators, and private-sector professionals — who face complex Social Security decisions often made more complicated by pension income and the WEP/GPO rules. Having a local RSSA® who understands this specific population is a meaningful advantage.
Virtual consultations available statewide. While Cassandra is based in El Dorado Hills and deeply connected to the Sacramento region, all consultations can be conducted via video — making this Social Security planning expertise accessible to clients anywhere in California.
Most Americans get their Social Security information from the Social Security Administration — which, by statute, cannot give personalized claiming advice — or from a financial advisor whose primary business is selling investment products. Neither source is optimized for the decision itself. Cassandra Barry's RSSA® credential, combined with her decade-plus background in insurance and retirement income planning, makes her genuinely different.
Whether you're five years from retirement or five months away, a Social Security planning consultation with an RSSA® can make a meaningful difference. Start with a free discovery call through 40 Quarter Coach.
An RSSA®, or Registered Social Security Analyst, is a financial professional who has completed a rigorous certification program through the National Association of Registered Social Security Analysts (NARSSA) focused exclusively on Social Security law, claiming strategies, and benefit optimization. Unlike a general CFP or financial advisor who may cover Social Security as one piece of a broader practice, an RSSA® has dedicated, specialized training in the specific rules that govern when and how you claim — including spousal coordination, survivor benefits, WEP/GPO for public employees, and how Social Security integrates with your overall retirement income. For Sacramento-area pre-retirees, having access to an RSSA® in El Dorado Hills means getting advice that is specifically designed for these decisions, not adapted from a broader financial planning context.
Yes. While Cassandra is based in El Dorado Hills and the partnership with 40 Quarter Coach serves the broader Sacramento region, all consultations can be conducted virtually. Clients in Folsom, Roseville, Granite Bay, Rocklin, Lincoln, Citrus Heights, Elk Grove, Auburn, and across Northern California routinely work through this process by video. The analysis — powered by the RSSA Roadmap® software — is entirely personalized to your earnings history and situation, so geography doesn't affect the quality of the work.
The Social Security Administration (SSA) is prohibited by law from giving personalized claiming advice. SSA representatives can tell you what your benefit amount will be at different ages, but they cannot tell you when you should claim, how to coordinate with a spouse, or how claiming at 62 versus 70 affects your lifetime income. An RSSA® like Cassandra can do all of that — using sophisticated software to model your specific situation, run break-even scenarios, and deliver a written strategy with a clear recommendation. That's the gap this service fills.
Potentially yes — and this is one of the most misunderstood areas of Social Security planning for Sacramento-region retirees. If you receive a pension from a government employer (such as CalSTRS or CalPERS) and also worked in Social Security-covered employment at some point, the Windfall Elimination Provision (WEP) may reduce your Social Security benefit. If you receive a government pension and are eligible for Social Security spousal or survivor benefits, the Government Pension Offset (GPO) may reduce or eliminate those benefits entirely. The RSSA Roadmap® software is specifically designed to model these scenarios accurately. Cassandra's training covers both provisions in depth, making her an especially strong resource for Northern California public employees navigating these rules.
The process through 40 Quarter Coach follows four structured steps. It begins with a free 15-minute discovery call to understand your situation and confirm this is the right fit. From there, a deep-dive session reviews your earnings record, benefit projections, family situation, and retirement timeline. Cassandra then produces a personalized RSSA Roadmap® analysis — a written document showing your Social Security options with specific recommendations and a clear action plan. Finally, follow-up support is available as your situation evolves. The goal is that you leave the process knowing exactly when to claim, exactly what your benefits will be, and exactly how they fit into your broader retirement income picture.
Disclosure: Cassandra Barry is an independent RSSA®-credentialed professional and a referral partner of 40 Quarter Coach. 40 Quarter Coach is not a licensed insurance agency and does not sell, recommend, or endorse any insurance products, carriers, or plans. 40 Quarter Coach is an independent, private fee-for-service consulting practice and is not affiliated with, endorsed by, or authorized by the Social Security Administration, Medicare, CMS, or any government agency. NARSSA has no affiliation with the Social Security Administration or any government agency. The RSSA® credential is issued by NARSSA and does not imply government endorsement or authorization.