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 & Responsibilities

Weekly 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 & Experience

Must-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+billiegraham@allsikes.com] :

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.