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 unicornsomeone 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:
- Bachelor's degree required; strong preference for business, finance, or economics majors
- 3-6 years of experience, ideally in private equity, investment banking, M&A, or strategic finance
- Prior exposure to cross-functional operations or working directly with a founder/executive
- Currently pursuing or planning to pursue an MBA or other advanced degree is a plus
- Strong written and spoken English; you may represent the founder in meetings and correspondence
- Proficiency with modern tools (Google Suite, Notion, Slack, Zapier, QBO, project management platforms)
Role Classification: Independent Contractor, 1099
Core Responsibilities:
Founder & Business Support
- Act as an extension of the founder owning follow-ups, driving decisions, and filling gaps
- Calendar management, scheduling, and meeting coordination
- Sit in on key meetings, take action points, and follow through
- Filter and manage communications, including inbox and task lists
Operations & Execution
- Coordinate and oversee project execution across the portfolio
- Assist with finance tasks: QBO entries, statement reviews, payment tracking
- Build repeatable systems and SOPs to optimize workflows
- Run special projects end-to-end: vendor sourcing, hiring, deal tracking
Strategy & Administration
- Research and prepare briefs on new business initiatives
- Assist in customer service, basic sales outreach, and internal team hiring
- Help maintain operational claritytrack KPIs, draft updates, build dashboards
- Support financial oversight: invoices, budget alignment, reconciliation tasks
Personal Life Support (As needed)
- Travel booking, gift sourcing, personal appointments, helping family with coordination
- Personal assistance with EA like activities as needed
Desired Traits & Skills:
- Organized, precise, steady, and takes pride in doing things right
- High conscientiousness and follow-throughyou don't drop balls
- Strong problem-solving, decision-making, and execution skills
- Capable of working independently while staying tightly aligned
- Exceptional communicatorboth in writing and in person
- Discreet, trustworthy, and ethically grounded
- Tech-forward and resourcefulable to build workflows and automate where possible
Benefits
- Monthly contractor rate of $2,500-$3,500 USD, depending on experience
- Includes a probationary period during the first 3 months at a slightly reduced rate
- Unlimited vacation - must oversee all responsibilities to ensure continuity at all times
- Role can scale with the businessthis is a potential long-term, growing opportunity
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 partnerthis could be the perfect opportunity. We're looking for someone exceptional. If that's you, apply now.
