Medicaid Annuity Paralegal

AshBer is seeking an experienced Medicaid Annuity Planner / Paralegal to join our national elder care team. This position is not entry level. This is an experienced role and is best suited for someone who already understands Medicaid strategy and eligibility planning.This role supports elder law attorneys nationwide by applying Medicaid strategy to Medicaid Compliant Annuity planning. It is a relationship-driven sales role focused on building trust with attorneys, supporting ongoing casework, and developing new business through professional outreach and networking. You will work directly with attorneys who expect thoughtful analysis, accuracy, professional judgment, and proactive communication. LocationPrimarily remote, with travel approximately once per month to elder law conferences, events, or educational programs. Preference for candidates located in the Midwest or Eastern U.S. to support efficient day‑trip travel to high‑volume Medicaid annuity states.What This Role Requires·       Prior hands-on experience with Medicaid eligibility or long-term care planning·       Working knowledge of Medicaid income rules, spend-down strategies, and penalty periods·       Strong math skills and comfort with financial calculations·       Confidence picking up the phone to communicate with attorneys and professional partners·       Comfortable in a relationship-driven sales role involving outreach, follow-up, and ongoing attorney communication·       Motivated by goals and results, with the ability to manage time and priorities in a largely self-directed work environment·       Calm and professional under end-of-month Medicaid planning pressure Key Responsibilities·       Prepare Medicaid focused planning letters and Medicaid compliant annuity quotesAnalyze income and asset data to support Medicaid planning strategiesApply state specific Medicaid rules to annuity planning structuresServe as the primary point of contact for assigned attorney relationshipsBuild and maintain attorney relationships through proactive phone, email, and in-person outreachConfidently speak at conferences, webinars, and professional education eventsQualificationsAt least two years of experience in Medicaid planning, elder law, or a closely related fieldLegal or paralegal experience strongly preferredDetail oriented, analytical, and compliance focusedStrong written and verbal communication skillsLicensingLife and or Health Insurance licenses preferred or willingness to obtain within six months.