June 24, 2026

Legal Executive Assistant

Senior • Remote

Washington, DC

The Opportunity

We're looking for an experienced Legal Executive Assistant to provide exceptional support to the Chief Estate Accountant and the Estate Administration team within the Private Wealth practice. This role is central to ensuring seamless operations and outstanding client service for Ultra High Net Worth individuals and families.

What You'll Do

  • Prepare and revise estate planning documents with precision and attention to detail
  • Manage complex calendars, schedule appointments, and coordinate travel arrangements
  • Oversee all aspects of new client intake and implementation
  • Maintain document retention systems, including vault documents and digital filing
  • Handle billing processes and client distributions
  • Support time tracking
  • Build and maintain strong client relationships with professionalism and discretion
  • Manage communications with internal and external stakeholders

Estate & Fiduciary Administration Support

  • Assist with preparation and organization of estate tax returns (Form 706), fiduciary income tax returns (Form 1041), and gift tax returns (Form 709)
  • Maintain detailed filing systems for estate and trust documentation in compliance with retention requirements
  • Track critical deadlines for tax filings, court accountings, and fiduciary reporting obligations
  • Coordinate collection and organization of financial data, asset valuations, and supporting documentation
  • Perform additional ad-hoc tasks as required

What We're Looking For

  • Minimum 5 years of executive support experience, preferably in professional services, accounting, or estate planning
  • Working knowledge of estate and trust taxation concepts; familiarity with Forms 706, 1041, and 709
  • Experience working with high-net-worth clientele
  • Comfort with AI tools and emerging technology to enhance productivity and workflow efficiency
  • Experience supporting C-suite executives or senior professionals
  • Exceptional organizational and deadline management skills
  • Advanced proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint)
  • Outstanding written and verbal communication skills
  • Ability to handle highly confidential information with absolute discretion

Benefits

  • Eligibility for Medical, Dental, and Vision insurance plans
  • 401(k) retirement program
  • Employment verification through E-Verify

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Remote

Alpharetta, GA

🏢 Summary: The offer is for an experienced Executive Assistant to support multiple C-Suite executives in a fast-paced, growth-stage environment. The role focuses on managing complex calendars, coordinating travel and meetings, preparing materials, and serving as a trusted partner to ensure executives are aligned with strategic priorities. It requires strong judgment, discretion, and the ability to operate cross-functionally with senior leaders and external stakeholders. 🗂️ Requirements: Minimum 5 years of Executive Assistant experience in a fast-paced, growth-stage organization, Direct experience supporting C-Suite executives, Ability to manage complex calendars across multiple time zones, Experience coordinating executive travel, meetings, offsites, and board-related activities, Experience handling sensitive and confidential information with discretion, Strong organizational and multitasking skills, Ability to track action items, expenses, and commitments accurately, Comfort working in ambiguous and rapidly changing environments 📃 Skills: CalendarManagement, TravelCoordination, MeetingCoordination, ExpenseReporting, TimeManagement, Documentation, Communication, ProjectManagement 🏢 Description: PlayOn is looking for a highly organized, proactive, and trusted Executive Assistant to support several C-Suite executives. This role will steward executives’ time, priorities, and attention by ensuring they are well-prepared, well-positioned, and focused on the work that matters most. Partnering closely with the Executive Assistant to the CEO, this Executive Assistant will manage complex schedules, manage travel, coordinate communications, and anticipate needs, while operating cross-functionally with senior leaders and external stakeholders. The Outcomes You’ll Deliver - Executives whose time and attention are aligned to the company’s highest priorities - Clear, well-managed calendars, meetings, and communications that enable effective decision-making - Strong preparation and follow-through for internal and external meetings - Smooth coordination across the C-Suite, senior leaders, and key external partners - A trusted partnership built on anticipation, discretion, and sound judgment - A professional brand suited to the executive suite that you’re managing In this role, you can expect to - Own and manage complex calendars across multiple time zones - Protect and promote the executive brand internally and externally - Act as a steward of executive time and attention - Proactively prepare leaders for meetings, including agendas, background materials, talking points, and follow-ups - Coordinate events with internal and external stakeholders - Coordinate logistics for meetings, offsites, board-related activities, and travel - Serve as a key point of contact between executives, senior leaders, board members, and external stakeholders - Track action items, commitments, travel arrangements, and expense reports - Anticipate challenges, flag risks, and solve problems before they escalate - Handle sensitive and confidential information with discretion and professionalism - Support special projects and strategic initiatives as needed To thrive in this role, you have - Demonstrated experience displaying exceptional judgment, discretion, and emotional intelligence - Minimum 5 years’ experience providing Executive Assistant support in a fast-paced, growth-stage organization with direct experience supporting the C-Suite and interacting with other executives - Strong organizational skills and ability to manage competing priorities - Proactive approach and ability to anticipate needs - Comfort working in ambiguous situations - Excellent strategic communication skills - Ability to ask clarifying questions and protect executive focus - Passion for operating in an environment where priorities evolve - Service-oriented mindset while operating as a true business partner The Benefits We Offer - Multiple medical insurance plans to choose from - Dental, vision, life and disability insurance - Employee Emergency Fund - Company equity (stock options) - Open PTO policy - 401K plan with company match - Hybrid/flexible work environment Note: Must be a full-time employee to participate in the company’s employee health benefit plan. Part-time employees and interns are not eligible to participate.