Executive Administrative Assistant

About the RoleThis is not a typical virtual assistant position.

We're looking for an AI-forward Executive Assistant with a Chief-of-Staff potential in the future who builds systems, owns outcomes, and drives the week to zero open tabs and inbox zero.You'll work directly with Billie Graham, a strategic leader managing multiple high-growth ventures across commercial construction, lead generation, nonprofit leadership, property management, and family.

Billie is based in Charlotte, NC, and needs someone who can anticipate needs, convert ambiguity into calendar blocks and checklists, and relentlessly close loops.The Goal : Expand capacity and increase velocity of execution through systems, AI automation, and proactive operational support.This role offers rare exposure to diverse industries while building the foundational processes that will enable rapid scaling.

You'll be part of the early team, collaboratively identifying tools and systems needed to achieve great outcomes.About Billie's VenturesAll ventures are in growth mode, and most do not have formal processes yet.

You'll solve for and document processes to allow rapid onboarding of future hires with repeatable results.Myers & Chapman – Strategic Markets Leader for Healthcare and Public Projects at this Commercial General ContractorLeads Exchange Group – Industry networking agency launching a new high-ticket service offering in

• ReGroup Carolinas – Board Member for this nonprofit focused on workforce development in construction tradesRental Property – Management of two rental unitsWho We're Looking ForWe need a systems-thinker with high agency who is AI-native, proactive, and relentlessly follows through.

You should be comfortable with ambiguity, able to convert loose ideas into structured action plans, and driven to improve workflows weekly.Critical mindset : We're looking for critical thinking over "task-taker."

You should anticipate needs, propose solutions, and own outcomes—not just execute orders.Personality Traits of Successful Candidates : Proactive and calm under pressureHighly organized and goal-orientedSystems-first thinker with high agencyPushes for clarity and closes loops consistentlyLow-ego, coachable, rigorous about details and dataComfortable saying "no / next" to protect prioritiesOperational Cadence & ResponsibilitiesWeekly Rhythm : Calendar & Commitments : Own and manage family / school / kids' activities, professional meetings, travel, and reservationsSend Friday Weekly Brief : next week at a glance, risks flagged, top 3 priorities identifiedInbox & Communications : Triage emails and meeting invites dailyFile receipts and manage reimbursementsMaintain stakeholder communication loopsTask System : Maintain running capture board across all venturesConvert texts / voice notes ? tasks with deadlinesConfirm task owner and status; nudge until doneResearch & Automation : Conduct project research and generate executive summariesWeb scraping and competitive trackingAutomate report generation and research tasksContact enrichment and CRM loggingPublic records, permits, budgets researchSOP Engine : Record Looms of recurring tasksShip 1+ SOP per week to the vaultDocument processes to enable future team scalingIterate and refine edge casesFamily / Personal Operations : Manage school communications and kids' calendarsCoordinate family travel and summer camp planningHandle household-related administrative tasksAI & Systems Improvement : Propose workflow automation improvements weeklyImplement AI tools to increase efficiencyBuild and optimize capture ? triage ? plan ? execute systemsRaise quality bars continuouslyRequired Skills & ExperienceMust-Have : 1–2 years minimum executive assistant or operations experienceAdvanced AI literacy : Fluent with ChatGPT, Copilot, and Perplexity; strong prompt crafting abilitiesCalendar triage & stakeholder management : Expert-level scheduling and communication coordinationResearch skills : Public records, permits, budgets, market intelligenceSOP creation : Ability to document processes via Loom-to-SOP workflowExcel / Power BI basics : Structured data work and simple reportingClear written English : Concise, action-oriented communication styleSecurity hygiene : Understanding of role-based access and data protectionDocumentation discipline : Rigorous attention to detailStrong interest in AI use cases and implementationNice-to-Have : Basic Python or no-code automation experience (Zapier, Make, n8n)AEC (Architecture / Engineering / Construction) familiarity : Procore, RFQ / RFP exposureWeb scraping capabilitiesHubSpot or CRM management experienceContact enrichment skills (LinkedIn, research tools)Power BI visualization and dashboard creationGolf handicap lookup experience (when relevant for relationship building)Tools & Platforms You'll UseEmail / SMS (Google & Microsoft suites)Ninety.io (project / goal management)ChatGPT, Copilot, Perplexity (AI tools – critical)Slack, Discord, Telegram (team communication)SharePoint, Google Workspace, MS Teams (document management)Excel (data organization)Additional tools to be collaboratively identifiedWhat We OfferCompensation : Starting at $1,100 USD per monthFull-time position : 40 hours per weekConsistent schedule : 8 : 00 AM – 5 : 00 PM EST, Monday–FridayFully remote : Work from anywhereDirect collaboration with an entrepreneurial leaderExposure to multiple industries : Construction, lead generation, nonprofit, real estateGround-floor opportunity : Help build foundational systems for scaling venturesLearning environment : Strong focus on AI implementation and automationCompany Culture & ValuesCulture in one line : We are problem solvers—systems over heroics—and the whole is greater than the sum of its parts.Core Values : IntegrityGrowth MindedIn Service to OthersProvide SolutionsOnboarding & SupportThere is currently no formal onboarding program—this will be part of the early partnership.

You'll collaboratively identify the tools and support structures needed to achieve great outcomes.

This is an opportunity to help shape the operational foundation from the ground up.Application ProcessPlease send the following to (

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