Full-Time Medicaid Annuity Planner / Paralegal (Experienced)

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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.

 

Compensation

$50,000 to $100,000 per year based on experience and licenses, plus bonuses, profit sharing, 401(k), paid time off, and holidays.

 

To apply or email your resume and cover letter to amber@ashber.com or click the button below.

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