Chief of Staff (Direct-to-Consumer Subscription Brand)

About the Role

The CEO currently manages roughly 25 people, agencies, and suppliers across Customer Service, TikTok Shop, Amazon, Operations, Retention, and Finance—plus a running list of ~20 ad hoc growth projects. There is no middle layer between the CEO and the work. Every decision, follow-up, deadline, blocker, and loose thread routes to one inbox.

The Chief of Staff will act as that layer, owning the operating system of the company: defining ownership, measurement, commitments, and outcomes. You’ll also handle a rotating portfolio of high-leverage projects end-to-end, manage the CEO’s calendar, inbox, and meeting follow-ups, ensuring their time is focused on product, partnerships, and P&L.

This is not a coordination role. You are expected to get into the weeds, execute work yourself, push teams, and raise the standard. You’ll report directly to the CEO with influence, not formal authority, and as you prove yourself, you’ll earn the authority to escalate, reassign, and address underperformance.

Career Path: If you excel, the path is clear—C-suite or President within two years. This is not a recruiting line; it’s a real opportunity.

Key Responsibilities

• Own accountability and urgency across every function, including TikTok Shop, Amazon, Operations, Retention, and Finance. Track KPIs, deadlines, and commitments, unblock bottlenecks, and ensure owners take ownership of outcomes.
• Build a comprehensive process map of the entire business: define roles, document responsibilities, create SOPs for recurring workflows, and establish clear reporting structures, bonus criteria, and performance metrics.
• Triage all items currently directed to the CEO. Handle, route, automate, or eliminate them to reduce his workload.
• Lead high-leverage projects end-to-end: scope, execute, hire/coordinate resources, and report progress weekly without micromanagement.
• Convert conversations into tracked action items. Capture decisions from meetings, Slack, or WhatsApp, assign owners, and follow up until completion.
• Manage the CEO’s calendar, inbox, and meeting prep with full ownership—scheduling, prioritization, prep materials, and follow-ups.
• Raise the bar for the team. Provide direct feedback, flag underperformance early, and empower managers to hold their teams accountable.

Requirements

Must-Have

• Ability to learn quickly and independently. If given a new tool (e.g., ClickUp) on a Friday, you’ll master it by Monday through tutorials, consulting, or self-directed study.
• Smart and hands-on problem-solving skills. You reason through complex business challenges and manage people effectively.
• Genuine humility and zero ego. You accept direct feedback, seek more of it, and never shy away from manual work (e.g., cleaning spreadsheets at 11 PM).
• Willingness to do the work yourself. Delegation without execution is a disqualifier.
• Comfort with ambiguity and total ownership. Approach unfamiliar domains with excitement, not fear.
• Directness in giving and receiving feedback without personal or political baggage.
• High work capacity: minimum 50 hours/week, with frequent nights and weekends. This is a fast-moving startup environment.
• Availability during US Eastern hours (9:00 AM – 12:00 AM ET).
• Excellent written and spoken English.

Nice-to-Have

• Track record of excellence in competitive environments (e.g., top academic performance, elite sports, high-level early-career roles, or a company you built).
• Experience in e-commerce (D2C, Amazon, or TikTok Shop), subscription models, or retention businesses.
• Background in Chief of Staff, founder’s associate, consulting, or investment banking.
• Experience building SOPs, process documentation, or operating cadences from scratch.
• Experience managing agencies and offshore contractors.

Note: Soft skills (e.g., adaptability, humility, directness) outweigh hard skills. A candidate with strong soft skills but less domain experience will be favored over a rigid domain expert.

Benefits

• Base Salary: $6,000 – $8,000 USD/month (negotiable for the right fit).
• Annual bonus: 20% of base, tied to project completion and KPI attainment.
• Employment structure: W-2 or 1099 (your choice).
• Remote work: Global flexibility with coverage of US Eastern hours.
• Career growth: Clear path to C-suite or President within two years for high performers.

The Culture

This is a high-performance environment with direct communication, no politics, and no vanity titles. Results drive promotions, bonuses, and authority. If you thrive in a fast-paced, standards-driven culture, this is a rare opportunity at scale with minimal bureaucracy.