Virtual Executive Assistant for a Caregiving and Support Services Company in the US (Home Based Full Time)

1. Calendar & Communications Management

Calendar Management

• Own and manage the principal's calendar across all entities — scheduling, rescheduling, and resolving conflicts proactively

• Coordinate internal meetings with staff (Director of Nursing, and HR/Benefits and Technology, and others)

• Schedule external meetings with attorneys, government contacts (DDS, DHCF), lenders, vendors, and contractors

• Issue meeting agendas and pre-meeting briefings; circulate follow-up action items afterward

• Maintain awareness of recurring deadlines: billing cycles, regulatory filings, loan payments, and lease

renewals

Email & Correspondence

• Monitor and triage email inbox across multiple accounts; flag urgent items, draft responses, and maintain Inbox Zero standards

• Draft, edit, and finalize professional correspondence — letters, memos, notices, and formal communications — in the principal's voice

• Convert voice-dictated messages into polished written correspondence

• Manage communication threads with external counsel, state agencies, financial advisors, and real estate partners

• Track outstanding responses and follow up on behalf of the principal

Phone & Contact Management

• Screen and log calls; relay messages accurately and promptly

• Maintain up-to-date contact database across all entities

• Coordinate conference calls and video meetings (Zoom, Teams, etc.); send invitations with dial-in details

2. Nonprofit Operations

Administrative & Regulatory Support

• Track and support compliance with DC, Maryland, and Virginia DDS/Medicaid regulatory requirements and reporting deadlines

• Prepare and format documentation for DDS/DHCF submissions, audit responses, and coalition correspondence

• Assist with coordination related to the Gainwell Medicaid billing platform — tracking enrollment status, escalating issues, and following up with agency contacts

• Maintain organized digital filing systems for regulatory documents, provider enrollment records, and correspondence

Human Resources & Staff Coordination

• Support HR documentation: termination letters, FMLA paperwork, disciplinary notices, and CMT-to-TME

certification tracking

• Coordinate onboarding logistics for new hires; prepare offer letters and orientation materials

• Track staff certification expiration dates (TME, eMAR, CPR, etc.) and issue advance reminders

• Maintain staff roster and assist with scheduling across 24+ locations

Technology & Program Rollouts

• Assist with coordination of the eMAR/iCareManager and TME rollout across all waiver settings — tracking training schedules, device assignments, and completion status

• Support the Remote Supports cohort rollout with Vista (contacts: Precious and Carlito)

• Coordinate tablet procurement logistics (iPads preferred) — vendor quotes, shipping, and inventory tracking

• Track fiber optic installation timeline and vendor milestones at the main office

Vendor & Contractor Coordination

• Manage vendor communications and service agreements for technology, facilities, and transportation

• Track fleet-related matters: citation reconciliation, toll accounts, and service records across 17 vehicles

• Support coordination with Special Olympics DC (Head Coach & Coordinator)

3. Real Estate Administration

Transactions & Leasing

• Coordinate with title companies (e.g., AWO Real Estate Title) on transaction documentation and closing logistics

• Track and organize lease agreements, certified check requirements, key pickup logistics, and move-in coordination for supported residents

• Maintain records for real estate LLCs and trust-related properties; prepare summaries of key terms and deadlines

• Liaise with lenders (e.g., EagleBank) on loan refinancing matters, document requests, and correspondence

4. Financial & Legal Coordination

Financial Administration

• Prepare expense reports and reconciliation summaries; coordinate with financial advisors (e.g., Solai)

• Support bank reconciliation efforts across multiple accounts (22 accounts); assist with Sage Intacct documentation

• Track invoice status, accounts receivable, and outstanding payables across entities

• Assist with preparation of materials for Board and leadership meetings

Legal Matter Support

• Coordinate with outside counsel; Brewer and University

Legal Services

• Organize and maintain legal files — correspondence, filings, discovery documents, and court dates

• Track deadlines for pending legal matters and send advance reminders

• Assist with document preparation related to estate and trust administration (five active trusts)

5. Travel, Events & Personal Logistics

Travel Coordination

• Research and book flights, hotels, and ground transportation for domestic and international travel (DC, London, West Africa/The Gambia, and beyond)

• Prepare detailed travel itineraries with confirmations, contacts, and logistics notes

• Coordinate travel arrangements for family members (including the principal's mother) as directed

• Track travel expenses and reconcile against budgets

Events & Special Projects

• Assist with event planning and logistics (family celebrations, organizational events, and related gatherings)

• Research venues, vendors, and accommodations; obtain quotes and make reservations

• Prepare run-of-show timelines and coordinate with on-site vendors

Personal & Miscellaneous

• Handle personal errands and administrative tasks as directed (appointments, deliveries, research)

• Manage gift sourcing, cards, and recognition for key relationships

• Conduct online research and prepare concise briefing summaries as requested