Chief of Staff (AI-Enabled Business Operations & Executive Support)

The Chief of Staff role at Paired combines business operations, executive support, commercial coordination, research, and AI-enabled execution. This position ensures the business moves forward while allowing the founder to focus on high-level decisions like closing deals and maintaining key relationships.

The scope of the role will expand as the individual learns the business and gains autonomy. While deep eCommerce or retention experience is not required, a genuine interest in developing expertise in this direction is essential. Paired seeks a capable, curious person who can grow with the role.

Responsibilities

• Day-to-day operations and founder support. Bring structure to priorities, communications, scheduling, outstanding tasks, invoice follow-ups, and other administrative work. Prepare concise updates showing what needs attention, what can be handled independently, and which decisions require the founder. Draft responses and ensure follow-ups are completed.
• Pipeline and outreach support. Research potential clients, maintain an organised pipeline, and prepare accurate, personalised outreach with relevant context. Track conversations, opportunities, and next steps. Initially, the founder handles outreach and sales conversations, with responsibilities transferring over time.
• Relationship intelligence and meeting follow-through. Turn calls and correspondence into useful notes, action items, and recommendations. Maintain context across relationships with brands, partners, platforms, and agencies. Connect information across conversations, identify opportunities, and suggest thoughtful ways to strengthen relationships.
• AI-enabled systems and coordination. Use AI tools and agents to support research, drafting, analysis, and repeatable workflows. Check the quality and accuracy of AI outputs, organise information in a central system, and progressively remove recurring work from the founder’s plate.
• Knowledge, content, and project coordination. Organise existing expertise, transcripts, saved resources, and content into accessible knowledge libraries. Help coordinate book-related projects, lead magnets, content repurposing, and promotional initiatives alongside existing contributors.
• Research and business improvement. Investigate relevant opportunities, connections, and information that could improve the business. Identify useful patterns in lead sources, sales cycles, conversion, and return on effort. Support other operational projects as priorities evolve.

Requirements

• Learning ability and genuine interest. Sharp, curious, and able to absorb new concepts quickly, with a real interest in building a career around eCommerce, customer retention, and business growth.
• Organisation, accuracy, and follow-through. Able to manage multiple moving parts, maintain reliable information, notice details, and carry work through to completion without repeated reminders.
• Proactive ownership and sound judgement. Notices problems and opportunities before being asked, proposes sensible next steps, and becomes increasingly comfortable making decisions independently.
• An AI-enabled approach to work. Willing to make AI a core part of daily execution and learn to work with agents and automation. Must critically assess AI outputs rather than assume they are correct.
• Clear communication and relationship awareness. Able to prepare useful 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.