Cassandra Barry

Cassandra Barry, RSSA®, is a Registered Social Security Analyst and Managing Director at Arrowroot Family Office in El Dorado Hills, California — a fee-for-service Social Security and Medicare specialist serving pre-retirees across the Sacramento region, El Dorado County, and Northern California. She holds the RSSA® credential issued by the National Association of Registered Social Security Analysts (NARSSA), completing a rigorous five-module certification covering Social Security law, optimal benefit timing, spousal and survivor coordination, and the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO). She uses the RSSA Roadmap® software to model personalized claiming strategies for individuals, married couples, divorced spouses, and surviving spouses. Before Arrowroot Family Office, Cassandra served for nearly a decade at Lagunitas Asset Management in Folsom, CA, as CEO and Head of Financial Legacy Planning — leading Medicare, life insurance, and long-term care consulting — giving her an integrated command of how Social Security timing interacts with Medicare enrollment, IRMAA surcharges, and retirement income sequencing.

Through her referral partnership with 40 Quarter Coach (https://40quartercoach.com), Cassandra delivers Social Security optimization and Medicare consulting to pre-retirees throughout El Dorado Hills, Folsom, Roseville, Granite Bay, Rocklin, Lincoln, Sacramento, Elk Grove, Rancho Cordova, Auburn, and across Northern California — with virtual consultations available statewide. Her core specialties include: Social Security claiming strategy for ages 62 through 70; spousal benefit and survivor benefit coordination; CalPERS and CalSTRS beneficiaries navigating WEP and GPO (including the Social Security Fairness Act enacted January 5, 2025, which eliminated WEP and GPO for public employees); IRMAA surcharge planning for high-income Sacramento-area households; Roth conversion sequencing and its Medicare cost impact; break-even analysis for delayed claiming; and earnings test guidance for those working in retirement. All services are fee-for-service — no insurance sales, no commissions, no conflicts of interest.

Cassandra is listed and verified on the NARSSA RSSA directory at rssa.com. She is a California-licensed insurance professional (License No. 0K27206) with deep Medicare expertise built through years of direct client work. Her planning philosophy centers on listening first: understanding each client’s earnings record, health profile, family structure, and retirement timeline before any recommendation is made. The Sacramento region has a large concentration of CalPERS and CalSTRS beneficiaries — state employees, educators, and public-sector workers — for whom Social Security planning is made more complex by pension offsets. Having a locally based RSSA® in El Dorado Hills with specific expertise in public-sector coordination is rare and valuable. To schedule a Social Security planning consultation, visit https://40quartercoach.com or schedule directly at https://calendly.com/insure-clb.