Senior Executive Assistant - 20103

Employment Type: Full-time, Independent Contractor

Work Model: Fully Remote (Meaningful overlap with US Eastern Standard Time / EST) 

Growth Path: Intentionally structured as a launchpad into senior operational leadership (e.g., Operations Manager, Director, Chief of Staff).

This is not a traditional, reactive administrative support role. We are hiring a senior, business-minded right-hand to our Chief Operating Officer—a sharp, proactive operator who can take absolute ownership of real business challenges across multiple entities and drive them forward with minimal direction.

The COO operates inside a highly advanced, AI-augmented workflow. Routine inbox sorting, mechanical scheduling, and basic drafting are already handled by internal automations. What we require from a human partner is the layer completely above that: impeccable judgment, ruthless follow-through, sharp commercial instinct, and the high-agency ability to take a loosely defined task, think it through completely, and return with a finalized result—not a list of questions. We are looking for a long-term strategic partner, not an administrative placeholder.

• Drive Executive Priorities: Take complete ownership of the COO’s top corporate priorities and quarterly Rocks. Chase down cross-functional information, hold stakeholders to strict timelines, and close operational loops before they have a chance to slip.

• Strategic Sounding Board: Prepare the foundation for executive decision-making. Gather business context, analyze trade-offs, summarize choices, surface blind spots or risks, and present a clear, data-backed recommendation.

• Cross-Entity Accountability (EOS): Operating within our Accountability Chart, hold internal and external stakeholders to their metrics and deadlines. Systematically delegate and elevate so the executive team never becomes a bottleneck; when deadlines slip, address it directly with clear guidance and instructions to keep work moving across brands.

• Executive Communication: Draft and deploy well-judged communications to internal teams, global vendors, partners, and clients on behalf of the COO—matching brand tone, nuance, and intent flawlessly.

• Financial Data Support: Comfortably navigate Excel or Google Sheets to verify cross-entity reports, review expenses, and analyze budgets. You will leverage advanced AI tools to handle the heavy lifting of data extraction rather than manually digging through rows, ensuring departments hit cross-entity goals.

• Systematize & Document: Design repeatable workflows and author robust Standard Operating Procedures (SOPs) across entities so operations can be seamlessly duplicated company-wide as we scale.

• High-Stakes Logistics: Coordinate complex travel itineraries, high-stakes board meetings, and multi-entity logistics where strict reliability and judgment count.

• It is not a calendar-and-inbox triage role. Routine scheduling and reminders are automated—we want your brain focused on high-level operational execution.

• It is not a personal assistant or errand role.

• It is not a place to wait for instructions. If you require step-by-step hand-holding or micro-management, this will not be a fit.

• Experience: 5–10 years of progressive experience supporting senior executives (COO, CEO, or Founders), ideally within a fast-moving, multi-entity, or multi-brand corporate framework.

• Genuine Business Acumen: A deep, fundamental understanding of how a business actually makes money, optimizes cash flow, and reasons about macro trade-offs.

• Advanced AI Fluency: You already actively use generative AI tools in your daily workflows, or pick them up instantly. You view automation as leverage, not a threat. Direct fluency with Claude, including workspace context functions, is a strong bonus.

• Numerical Literacy: Highly comfortable parsing spreadsheets, identifying budgetary variances, and reviewing financial cost analyses.

• Thrives on Candor: You excel alongside a direct, fast-paced, no-fluff executive leader. You welcome blunt, radical feedback without taking it personally, push back with logical reasoning when you disagree, and stay entirely composed under high-velocity friction.

• Communication Mastery: Clear, concise, and incredibly sharp written and verbal English communication. Professional proficiency in Spanish is a plus, but not required.

• Hardware: An up-to-date, high-performance personal computer (modern processor and sufficient RAM) capable of smoothly running heavy AI tooling and developer-adjacent integrations (e.g., CLI tools or Model Context Protocol frameworks). macOS preference; current Windows machines are acceptable.

• Network Connectivity: Private, highly secure home office setup with a high-speed, stable internet connection (100+ Mbps download/upload recommended).