Chief of Staff - job 1 of 4

Job Title: Chief of Staff

Type: Full-Time, Remote LATAM

Working Hours: Monday to Friday - 11 am to 7 pm EST

Compensation: USD $3500 - 3800 (Salary based on assessment)

About the Company and opportunity:

Our clients are two dynamic entrepreneurs based in Philadelphia USA and with a diverse and growing portfolio of business ventures and personal projects spanning technology, real estate, hospitality, and private family matters across the United States, Italy, and Guatemala. They are seeking a highly organized, proactive, and trustworthy Chief of Staff to act as our strategic partner and operational integrator. Your mission will be to bring structure to their vision, drive key projects forward, and create leverage that allows us to focus on high-level growth and strategy.

Job Description:

The Chief of Staff (CoS) will serve as the right hand to the principals, ensuring that their strategic priorities are translated into actionable plans and executed flawlessly.

You will manage a wide range of projects, from overseeing a tech startup, development to coordinating international real estate ventures and building the foundation for a family office. The ideal candidate is a master of project management, an exceptional communicator, and a natural leader who can manage both people and processes with efficiency and discretion

Key Responsibilities

Strategic Project & Business Management:

• Drive key business initiatives from conception to completion, ensuring projects are delivered on time and within budget.

Fiduciary Tech Venture:

• Develop and maintain overall project plans in coordination with family office principals. Coordinate among stakeholders.

• Manage tech development teams; assist with UI/UX development by providing feedback on storyboards and Figma designs.

• Participate in key team meetings, take notes, provide summaries and feedback.

• Interface with legal counsel.

• Create, update, and maintain the business plan, investor presentation, customer presentation, financial model, and CRM of prospective clients and partners.

International Projects (Milan, Italy):

• Act as the central point of coordination for family, legal counsel, and other stakeholders.

• Source, vet, and manage relationships with Italy-based service providers, including accountants, lawyers, architects, and contractors.

• Conduct quantitative analyses as necessary.

New Ventures (e.g., Guatemalan Rum):

• Serve as the primary liaison with external partners, ensuring clear communication and alignment on project goals.

Family Office Development:

• Lead the initiative to establish a formal family office structure.

• Build and maintain a centralized inventory of professional contacts (legal, financial, etc.) across the US, Italy, and Guatemala.

• Handle sensitive and confidential personal projects, such as coordinating with legal counsel for prenuptial agreements.

Operations & Team Management

• Recruit, onboard, and manage a team of part-time virtual assistants, operations associates, and specialized contractors as needed.

• Delegate tasks effectively, providing clear instructions and holding team members accountable for results.

• Develop and implement standardized operating procedures (SOPs) and systems to improve efficiency across all business units.

• Oversee and streamline support for existing hospitality businesses (Restaurants; Catering), including:

  • Implementing maintenance schedules and managing vendor relationships.

  • Developing and refining operations manuals and business expansion Models.

  • Ensuring systems are in place to handle customer inquiries and catering logistics.

Financial & Administrative Oversight

• Manage the process for paying overseas contractors and vendors.

• Oversee expense tracking and reporting for various business entities and personal accounts (e.g., Aegle, Fiduciary).

• Coordinate with bookkeepers and accountants to ensure financial accuracy.

• Manage key administrative and compliance tasks for construction and property management, including overseeing insurance, licensing, and the permit application process.

Requirements

• Experienced Operator: You have 5+ years of experience in a Chief of Staff, operations management, or senior project management role, preferably supporting C-level executives or entrepreneurs.

• Bilingual & A Superb Communicator: You have professional fluency in both English and Spanish (written and verbal). You communicate with clarity, precision, and empathy.

• Master of Organization & Project Management: You can juggle multiple complex projects simultaneously without letting anything fall through the cracks.

• You live by your systems (e.g., Asana, Trello, Notion).

• Proactive & Autonomous: You don’t wait to be told what to do. You identify problems, propose solutions, and take ownership of the outcome. You are comfortable working independently in a remote environment.

• Financially Literate: You are comfortable creating business models, managing budgets, and overseeing financial administration.

• Tech-Savvy: You are proficient with modern business software, including project management tools, CRMs, and communication platforms. Experience with Figma is a plus.

• Utterly Discreet: You will be handling highly confidential business and personal information, and your integrity and discretion are non-negotiable.