Chief of Staff - Remote, Full Time Contractor

Job Description Overview :

We are seeking a sharp, business-savvy Chief of Staff to support the founder in managing and scaling a diverse, fast-moving portfolio of businesses across e-commerce, virtual staffing, entertainment, and physical operations. This role is fully remote, interacting with teams distributed globally, on-the-ground teams, and physical assets.

This is a hybrid strategic and tactical position, ideal for someone who can toggle between high-level business initiatives and meticulous execution. We're looking for a unicorn—someone who thinks like a founder, is grounded in execution, thrives in ambiguity, and can fill in the blanks with good judgment and speed. A strong finance foundation is valuable, but this role goes beyond, requiring the ability to take ownership of projects, make sound business decisions, and act as an extension of the founder with an operational lens.

About The Businesses

The founder operates a growing portfolio of seven (and counting) companies in various industries. These ventures are lean, agile, and reliant on tight operational execution, data-driven decision-making, and cross-functional support. From team building to vendor negotiations, from financial reviews to special projects, the work is dynamic, varied, and always evolving.

Requirements

Required Availability :

• 45-55+ hours / week on average, fully remote
• Flexible, on-call nature; must be responsive during the founder's waking hours (approx. 8am-10pm EST)
• Requires weekday evening and some weekend availability, with some flexibility depending on workload
• Must be responsive and reliable, especially during US business hours
• Must have full ownership of responsibilities and oversee projects & tasks even during PTO to ensure continuity
• Occasional travel support and availability during international travel is required

Education & Experience :

Role Classification : Independent Contractor, 1099

Core Responsibilities :

Founder & Business Support

Operations & Execution

Strategy & Administration

Personal Life Support (As needed)

Desired Traits & Skills :

Benefits

If you're looking for a role where you can make a real impact, move fast, learn across industries, and act as a true business partner—this could be the perfect opportunity. We're looking for someone exceptional. If that's you, apply now.

Skills Required

google suite , Slack