Executive Administrative Assistant

About the Role This 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 Ventures All 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 Contractor Leads Exchange Group – Industry networking agency launching a new high-ticket service offering in 2025 ReGroup Carolinas – Board Member for this nonprofit focused on workforce development in construction trades Rental Property – Management of two rental units Who We're Looking For We 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 pressure Highly organized and goal-oriented Systems-first thinker with high agency Pushes for clarity and closes loops consistently Low-ego, coachable, rigorous about details and data Comfortable saying "no/next" to protect priorities Operational Cadence & ResponsibilitiesWeekly Rhythm: Calendar & Commitments: Own and manage family/school/kids' activities, professional meetings, travel, and reservations Send Friday Weekly Brief : next week at a glance, risks flagged, top 3 priorities identified Inbox & Communications: Triage emails and meeting invites daily File receipts and manage reimbursements Maintain stakeholder communication loops Task System: Maintain running capture board across all ventures Convert texts/voice notes → tasks with deadlines Confirm task owner and status; nudge until done Research & Automation: Conduct project research and generate executive summaries Web scraping and competitive tracking Automate report generation and research tasks Contact enrichment and CRM logging Public records, permits, budgets research SOP Engine: Record Looms of recurring tasks Ship 1+ SOP per week to the vault Document processes to enable future team scaling Iterate and refine edge cases Family/Personal Operations: Manage school communications and kids' calendars Coordinate family travel and summer camp planning Handle household-related administrative tasks AI & Systems Improvement: Propose workflow automation improvements weekly Implement AI tools to increase efficiency Build and optimize capture → triage → plan → execute systems Raise quality bars continuously Required Skills & ExperienceMust-Have: 1–2 years minimum executive assistant or operations experience Advanced AI literacy : Fluent with ChatGPT, Copilot, and Perplexity; strong prompt crafting abilities Calendar triage & stakeholder management : Expert-level scheduling and communication coordination Research skills : Public records, permits, budgets, market intelligence SOP creation : Ability to document processes via Loom-to-SOP workflow Excel/Power BI basics : Structured data work and simple reporting Clear written English : Concise, action-oriented communication style Security hygiene : Understanding of role-based access and data protection Documentation discipline : Rigorous attention to detail Strong interest in AI use cases and implementation Nice-to-Have: Basic Python or no-code automation experience (Zapier, Make, n8n) AEC (Architecture/Engineering/Construction) familiarity: Procore, RFQ/RFP exposure Web scraping capabilities HubSpot or CRM management experience Contact enrichment skills (LinkedIn, research tools) Power BI visualization and dashboard creation Golf handicap lookup experience (when relevant for relationship building) Tools & Platforms You'll Use Email/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 identified What We Offer Compensation: Starting at $1,100 USD per month Full-time position: 40 hours per week Consistent schedule: 8:00 AM – 5:00 PM EST, Monday–Friday Fully remote: Work from anywhere Direct collaboration with an entrepreneurial leader Exposure to multiple industries: Construction, lead generation, nonprofit, real estate Ground-floor opportunity: Help build foundational systems for scaling ventures Learning environment: Strong focus on AI implementation and automation Company Culture & Values Culture in one line: We are problem solvers—systems over heroics—and the whole is greater than the sum of its parts. Core Values: Integrity Growth Minded In Service to Others Provide Solutions Onboarding & Support There 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 Process Please send the following to (operations+ ) : Resume: As a PDF titled (Lastname.Firstname.ExecutiveAssistant.pdf) Cover Letter addressing: How you meet the required skills and experience Specific examples of systems or SOPs you've built Your experience with AI tools (ChatGPT, Copilot, Perplexity, automation tools) A time you anticipated a leader's needs and proactively solved a problem How you've closed loops and driven projects to completion Why you're interested in supporting multiple ventures simultaneously AI Competency Example: Share a specific example of how you've used AI tools to automate a workflow, solve a problem, or improve efficiency Email Subject: Systems Over Heroics Timeline: We aim to fill this position within 2–3 weeks. Well-structured and thoughtful applications demonstrating critical thinking and systems-first approach will stand out. If you have questions about the role, feel free to include them in your message.