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Contractor - Chief of Staff - Remote at The People Group. Job Description Overview:. We are seeking a highly intelligent, detail-oriented, and operationally minded Chief of Staff to support the founder in managing and scaling a diverse and growing portfolio of businesses—both virtual and physical. The businesses span operations, e-commerce, entertainment, and virtual staffing, with teams distributed globally and a few in-person operations. While the role itself is fully remote, the scope of work will certainly touch physical operations in some businesses.. 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 EA 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.. About the Businesses. The founder operates a growing portfolio of seven (and counting) companies in various industries. These ventures are lean, fast-moving, and highly dependent on operational excellence, strategic oversight, and cross-functional collaboration. From team building to vendor negotiations, from financial reviews to special projects, the work is dynamic, varied, and always evolving.. 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 preferred (business, operations, or related fields). . Strong preference for candidates with finance or accounting background. . 3–5+ years in a Chief of Staff, operations, or cross-functional support role. . Prior experience working directly with a founder or executive leader. . 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 clarity—track 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. . Vendor management and occasional dispute resolution. . Desired Traits & Skills:. . Organized, precise, steady, and takes pride in doing things right. . High conscientiousness and follow-through—you don’t drop balls. . Strong problem-solving, decision-making, and execution skills. . Capable of working independently while staying tightly aligned. . Exceptional communicator—both in writing and in person. . Discreet, trustworthy, and ethically grounded. . Tech-forward and resourceful—able to build workflows and automate where possible. . Company Location: Philippines.