Estate Planning Drafting Paralegal

Sheppard Law Firm is seeking a full\-time estate planning drafting paralegal to join our Fort Myers office. We’re a boutique estate planning firm with over 100 years of service in Southwest Florida, and we’re looking for someone who wants to grow in a professional, team\-oriented environment. This position works directly with our partner Michael Hill, who leads our estate planning division. You’ll be responsible for drafting the full range of estate planning documents using WealthDocs (HotDocs\-based), working closely with our attorneys, and providing clear communication with clients and their advisors. This is not a behind\-the\-scenes job. While you won’t give legal advice, you’ll be an integral part of our client experience — ensuring that documents are prepared accurately, efficiently, and in a way that reflects each client’s personal and financial goals. **Who We’re Looking For** The right candidate will: * Take ownership of their work and pride in getting the details right. * Think critically and catch issues before they become problems. * Be growth\-oriented — professionally, personally, and intellectually. * Communicate clearly and comfortably with clients, attorneys, and team members. * Enjoy working in a structured system with room to improve how we do things. * Be genuinely interested in helping clients — and not just checking boxes. **Why Work With Us** We take a proactive, relationship\-driven approach to estate planning — and that means we value the people behind the work. You’ll have a seat at the table, the support of experienced professionals, and opportunities to grow in responsibility over time. To apply, send your resume along with a short cover letter explaining what you enjoy about legal drafting or working in a client\-focused legal setting. **Skills \& Requirements** The ideal candidate is highly proficient in Microsoft Word — not just for basic typing, but for formatting complex legal documents with accuracy and efficiency. Strong typing skills and close attention to detail are essential, along with the ability to proofread your own work and spot errors before they go out the door. You should be comfortable working within templates and automation systems. Prior experience with WealthDocs (or any HotDocs\-based document drafting software) is strongly preferred. Familiarity with estate planning documents — including wills, revocable and irrevocable trusts, and powers of attorney — is helpful. That said, we’re willing to train the right person who brings strong technical ability, good judgment, and a desire to learn. Excellent communication skills are a must. You’ll be expected to interact with clients, attorneys, and financial professionals, and you should be comfortable doing so in a clear, professional, and personable manner — both verbally and in writing. This is not a position for someone who needs to be micromanaged. We’re looking for someone who takes ownership of their work, manages multiple projects at once, and meets deadlines without needing to be reminded. You’ll be part of a highly collaborative team, but you’ll also need to work independently and follow through consistently. Our firm culture values consistency, professionalism, and mutual respect. Many members of our team have been with us for over a decade, and several recently retired employees were with the firm for 40 and even 50 years. If you’re looking for a long\-term professional home — not just your next job — this is the kind of place where people build careers. We offer great benefits paid for by the firm, including health insurance, a health insurance gap policy, life insurance, and 401(k) match after eligibility period, and even a team bonus when we receive 5 Star Google Reviews. We also offer additional programs you may enroll in, including dental and disability insurance. Pay is commensurate with your experience. It is common for us to pay a generous end of year bonus when we have a good financial year, which is dependent upon the quality of our team. We value our team members. **To apply for this position, please follow these instructions precisely:** **1\) Write an email to hiring@sheppardlawfirm.com** **2\) Set the subject line of your email as "I'm a Legal Document Specialist!"** **3\) In the body of your email, please include a paragraph explaining why you believe you are the right fit for this role, considering the qualities and skills we've outlined.** **4\) Please also attach your resume in the email as a PDF.** Job Type: Full\-time Pay: $800\.00 \- $900\.00 per week Benefits: * 401(k) * 401(k) matching * Dental insurance * Employee discount * Flexible schedule * Health insurance * Life insurance * Paid time off * Vision insurance Ability to Commute: * Fort Myers, FL 33919 (Required) Ability to Relocate: * Fort Myers, FL 33919: Relocate before starting work (Required) Work Location: In person