Inside Out Hiring

IMPORTANT - Watch this quick Loom video on how to get hired:
https://www.loom.com/share/345f776084e642ba99c24aabe40a67a0

C1 ENGLISH LEVEL IS REQUIRED, THE SELECTED CANDIDATE WILL BE SPEAKING STRICTLY IN ENGLISH DURING THEIR WHOLE SHIFT.

PLEASE SUBMIT YOUR RESUME AND AUDIO RECORDING IN ENGLISH

 

About the Client:

Our client is a high-velocity entrepreneur, multi-business owner, and U.S. Marine Corps veteran who leads a fast-moving portfolio of ventures spanning business consulting, hospitality, entertainment, real estate, and executive leadership development. His primary operations include:

• Business Consulting & Financial Services: A dedicated firm providing financial optimization, startup consulting, payroll prep, and business strategy focused heavily on supporting the Hispanic market.
• Hospitality & Entertainment Ventures: A parent group managing a sports bar and lounge, a city tour trolley operation, and an active food truck integration.
• Real Estate & Contracted Operations: Independent project management overseeing long-term rentals, short-term Airbnb properties, and a leadership training program.

Because the founder operates across multiple unrelated industries, he relies heavily on strict calendar discipline and leads with a direct, fast-paced, military-style communication style. He values candid efficiency, direct feedback, and high individual accountability over hand-holding. He is seeking a high-caliber partner who can navigate high-level strategic support, financial tracking, and operational chaos with clarity, organization, and complete composure.
 

About the Role:

This is not a traditional administrative position—it is a proactive operational partnership. As the Executive Assistant, you will sit at the center of the founder’s ecosystem, managing both business administration and high-priority personal tasks ("life admin" such as travel arrangements, vendor management, and personal scheduling).

Your main mission is to free up executive capacity by taking full ownership of recurring workflows, anticipating needs before they arise, and operating as an independent problem-solver across all business lines. You will take the lead on financial and payroll preparation (using QuickBooks and Google Sheets), generate reports and PowerPoint decks for key stakeholders, take contextual minutes during virtual meetings, and execute multi-entity research.

By using modern AI platforms (specifically Claude) as a primary "thinking partner" and documenting workflows into clear, repeatable SOPs, you will build structure out of ambiguity so the founder can focus entirely on high-level business growth.

Key Responsibilities

• Executive Organization & Calendar Management: Proactively manage complex calendars, manage inboxes, eliminate scheduling conflicts, and protect focused working blocks.
• Virtual Meeting Minutes & Action Items: Virtually join recurring business meetings to take clear, contextual minutes and turn high-level discussions into trackable, executed action items.
• Financial & Payroll Preparation: Assist in preparing payroll, spreadsheets, and routine accounting tasks in QuickBooks and Google Sheets for the Founders review and final approval.
• Stakeholder Reporting & Presentations: Build polished PowerPoint presentations, executive summaries, and visual handouts for shareholders, business partners, and clients.
• Multi-Entity Research & AI Integration: Utilize AI tools (specifically Claude) as a critical-thinking partner to conduct deep research across Founders varied ventures (consulting, hospitality operations, real estate, and project rollouts like the food truck).
• System Building & Visual SOPs: Document repetitive tasks into visual, step-by-step SOPs (e.g., using Scribe or detailed process maps) to build permanent company documentation.
• Personal Life Administration ("Life Admin"): Handle personal logistics including domestic/international travel bookings, finding home service vendors (cleaners, contractors), dinner reservations, and personal schedule management.

Non-Negotiable Qualifications & Attributes

• Bilingual Fluency (Non-Negotiable): Complete verbal and written mastery of both English and Spanish.
• High-Level Critical Thinking & Autonomy: Proven ability to figure out intermediate steps to reach a high-level goal independently without requiring micromanagement or constant reassurance.
• Direct Communication Resilience: Comfortable receiving candid, direct feedback without taking it personally; engineered to work well alongside military-style efficiency and straightforward direction.
• Advanced Google Sheets & Financial Tooling: Strong, practical knowledge of Google Sheets (including proficiency with formulas, data layout, and tracking) alongside basic-to-intermediate QuickBooks experience.
• Modern AI Proficiency: Daily hands-on experience leveraging Claude (or ChatGPT) as a primary workflow accelerator and "thinking partner."
• Behavioral Adaptability: Willingness to undergo baseline team style assessments (e.g., Working Genius) to ensure seamless workflow integration and communication alignment.