Compliance Paralegal - Remote / Telecommute

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.

Location
Primarily 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 quotes
Analyze income and asset data to support Medicaid planning strategies
Apply state specific Medicaid rules to annuity planning structures
Serve as the primary point of contact for assigned attorney relationships
Build and maintain attorney relationships through proactive phone, email, and in-person outreach
Confidently speak at conferences, webinars, and professional education events

Qualifications
At least two years of experience in Medicaid planning, elder law, or a closely related field
Legal or paralegal experience strongly preferred
Detail oriented, analytical, and compliance focused
Strong written and verbal communication skills

Licensing
~ Life and or Health Insurance licenses preferred or willingness to obtain within six months.