Chief of Staff (Remote, Freelance/Contract)

Paired is a global staffing and recruiting agency that connects remote talent with top-tier companies worldwide. Their mission is to provide meaningful jobs to skilled individuals, regardless of location.

The client is seeking a Chief of Staff to blend business operations, executive support, commercial coordination, research, and AI-enabled execution. This role ensures the business operates smoothly while allowing the founder to focus on high-level priorities like closing deals, maintaining key relationships, and making strategic decisions.

The scope of the role will expand as the individual learns the business and gains autonomy. Deep eCommerce or retention experience is not required—genuine curiosity and a willingness to develop expertise in these areas are essential. The ideal candidate is capable, adaptable, and eager to grow with the role rather than fit a predefined checklist.

Responsibilities

• Manage day-to-day operations and support the founder by structuring priorities, communications, scheduling, and administrative tasks. Draft concise updates to clarify what needs attention, what can be handled independently, and which decisions require the founder’s input. Ensure follow-ups are completed.
• Support pipeline and outreach efforts by researching potential clients, maintaining an organized pipeline, and preparing personalized outreach materials. Track conversations, opportunities, and next steps. Initially, the founder handles outreach and sales conversations, but responsibilities will gradually shift toward the Chief of Staff.
• Develop relationship intelligence by converting calls and correspondence into actionable notes, recommendations, and follow-up tasks. Maintain context across relationships with brands, partners, platforms, and agencies, identifying opportunities to strengthen connections.
• Leverage AI tools and agents to streamline research, drafting, analysis, and workflows. Critically evaluate AI outputs, organize information in a central system, and progressively reduce repetitive tasks for the founder. The role involves managing AI-assisted workflows—not passively accepting AI-generated content.
• Organize existing expertise, transcripts, and resources into accessible knowledge libraries. Assist with book-related projects, lead magnets, content repurposing, and promotional initiatives, collaborating with other contributors. Writing, design, or content creation expertise is not required.
• Conduct research to identify business opportunities, connections, and improvements. Analyze lead sources, sales cycles, conversion patterns, and return on effort to inform strategic decisions. Support evolving operational projects as priorities shift.

Requirements

• Strong learning ability and genuine interest in eCommerce, customer retention, and business growth. Quickly absorb new concepts and demonstrate enthusiasm for career development in these areas.
• Exceptional organizational skills, accuracy, and follow-through. Manage multiple tasks simultaneously, maintain reliable information, and complete work without repeated reminders.
• Proactive ownership and sound judgment. Anticipate problems and opportunities, propose solutions, and gradually take on independent decision-making while recognizing when founder input is needed.
• An AI-enabled approach to work. Willingness to integrate AI into daily tasks and learn to work with agents and automation. Must critically assess AI outputs rather than assume correctness.
• Clear communication and relationship awareness. Prepare concise summaries, thoughtful outreach, and appropriate responses while understanding the context and commercial significance of different relationships.
• Trustworthiness and long-term commitment. Discreet, dependable, and interested in becoming a trusted partner over several years. Comfortable handling both administrative and strategic responsibilities as the role evolves.