Strategic Executive Assistant to the CEO

The Vision At AI Leadership, we believe in clarity, structure, and well-run operations that allow our team to focus on the work that creates the greatest impact. The Strategic EA role exists to provide end-to-end leverage to the CEO by owning tactical and operational execution: inbox, calendar, logistics, and meeting prep. We are looking for a \"thinking partner\" who can maintain the highest standards of operational excellence and brand representation. Who We're Looking For The Strategic Executive Assistant (EA) will act as the CEO's \"20% focus\" unlock, allowing him to drive 80% of business outcomes. This is not a role for someone who only follows rigid rules; we need an individual who can operate with nuance, anticipate needs before they are stated, and understand the CEO's unique decision-making framework. You will be measured on your ability to triage the CEO's inbox to 95% without escalation and reduce calendar friction to near-zero. If you are a high-nuance individual who \"just gets it\" and thrives in a fast-paced environment, this role is for you. Why You Should Join Us AI Frontier: Gain direct exposure to the AI space and learn to build and refine AI-driven automation. Career Growth: We are a growing organization that values internal mobility; this role has a path toward operations or management, as demonstrated by previous incumbents. High-Impact Environment: Work alongside experienced leaders who prioritize growth, ambition, and proactive problem-solving. Role Responsibilities The 20% That Drives 80% of Success Inbox Ownership: Manage the CEO's inbox end-to-end, responding to all messages within 24 hours using his tone and zero \"emotional leakage\". Strategic Calendar Defense: Own the calendar to ensure it reflects strategic priorities; proactively identify gaps or blockers and coordinate with the family assistant to honor personal time. Flawless Travel & Logistics: Execute end-to-end travel (flights, hotels, ground transport) and remain on-call for any transit issues. Meeting Readiness: Maintain prep docs and ensure the CEO is fully prepared for every internal and external stakeholder interaction. The Remaining 80% HubSpot & CRM Maintenance: Review deals weekly, ensure follow-up tasks are executed on time, and load new contacts sourced by the CEO. SOP & Notion Management: Fully own and update all CEO-related workflows and databases, ensuring documentation is audit-ready and searchable. Small-Scope Project Management: Lead projects assigned by the Exec Ops Manager, assessing needs, developing plans, and communicating status to stakeholders. Skills & Attributes We're Looking For Methodical & Nuanced: You understand the difference between tactical execution and strategic decision-making and can operate independently in ambiguous situations. 1–3 Years of Relevant Experience: Ideally supporting senior leaders or working in high-growth, corporate, or communications-heavy environments. Proactive Tech-Savviness: Proficiency with Google Workspace, Slack, HubSpot (or similar CRMs), and Notion, plus a strong drive to use AI tools for speed and efficiency. Executive Presence: You have a professional audio/video setup and communicate with the polish required for CEO-facing interactions. Coachability: You believe feedback is the \"breakfast of champions\" and iterate quickly based on guidance. Our Values Create remarkable experiences – Every interaction is a chance to satisfy customers and internal team members. Always be growing – Committed to continuous improvement and individual learning. Deliver results – Taking initiative to solve problems and drive success regardless of formal responsibility. Do the right thing – Prioritizing integrity, respect, and discretion in all interactions. Practice what we teach – Pushing the boundaries of what it means to be AI-driven. Compensation & Location Compensation: Starts at $2,200 USD Location: Remote (Working within 8 AM - 5 PM CST is preferred). Application & Selection Process TO APPLY: Send your Resume (PDF titled \"Lastname.Firstname.EA.pdf\") to [Operations+AIL@allsikes.com]. Record a short demo video (2 - 4 mins max) highlighting your relevant experience for the role, skills, successes, and goals for the future. Also, we'd like you to briefly mention the following insights: Process Optimization Proposal: Share an example of how you've improved an operational workflow in the past (Preferably using AI or automation tools). We want you to showcase your personality, and why you believe you are the ideal candidate for the Strategic Executive Assistant role. Our process is thorough but rewarding. Here is what you can expect: Technical AI Prompt Test and Strategic Thinking Exercise Behavioral Assessments: Working Genius (to assess natural strengths) and Kolbe A Index. Three-Step Interview sequence: Initial Screening call → Head of Operations → CEO.