Chief of Staff & AI Systems Partner for a USA Founder (Remote)

Job Description

Paired is a global staffing and recruiting agency that specializes in pairing remote work with top-tier talent. We admire the importance of innovative social media strategies and are committed to connecting talented individuals with great companies that need their unique skills. Our mission is to provide great jobs to talented people, no matter where they are located.

This role is for someone in all LATAM who wants to operate at a Chief-of-Staff / Systems Architect level, combining systems thinking and AI fluency to help scale a high-touch, high-impact personal transformation business working with founders, investors, and post-exit entrepreneurs.

This is a 2–5 year partnership trajectory with fractional ownership upside for the right person. We’re building movements with top-tier organizations (e.g. Light Dark Institute) and need someone who can operate at a high level of trust, autonomy, and strategic altitude.

Top talent doesn’t want a job, they want a Lab. This role offers portfolio-worthy challenges, real leverage, and the opportunity to co-design a life and business as a living experiment.

What You’ll Do (Depending on Your Strengths)

This role can lean more AI-first or more Chief-of-Staff / Operations-first — strong candidates may span both.

Systems & Operations (Chief of Staff–style)

• Act as an operating system for a high-agency founder with a complex life and business.
• Control attention flow: decide what reaches the founder, what gets delegated, and what gets systemized.
• Design and document workflows and SOPs so problems are solved once, not repeatedly.
• Oversee logistics for retreats, programs, and experiments while protecting quality and “vibe.”
• Coordinate and lead generalist assistants through clear systems, not constant supervision.

AI & Automation (AI Architect–style)

• Design AI-native, prompt-driven systems that support decision-making, context management, and operations.
• Build transcript-based and knowledge systems (calls, notes, content, history → insights and actions).
• Create AI agents and workflows that handle research, logistics, follow-ups, and coordination.
• Design dashboards or interfaces that surface clarity, priorities, and system health.
• Continuously refine systems based on real-world use, not theory.

Requirements

You can be strong in both areas below, or clearly strong in just one of them.

• AI / Systems Automation Profile
• Strong AI fluency: understands how to design AI-native systems, not just use tools.
• Experience building prompt-driven workflows (AI + logic + data + tools).
• Ability to turn messy inputs (calls, notes, content, history) into structured outputs and actions.
• Experience with AI agents, RAG-style systems, or context-aware automations.
• Comfortable choosing where AI adds leverage vs where humans should stay involved.
• Thinks in systems and outcomes, not isolated automations.
• Chief of Staff / Operations Profile
• Strong systems thinking applied to real-world operations.
• Experience acting as a force multiplier for a founder or senior operator.
• Ability to control priorities, filter noise, and protect focus.
• Skilled at designing workflows and SOPs so work scales without constant oversight.
• Comfortable making judgment calls without detailed instructions.
• Experience coordinating people, projects, and logistics in complex environments.
• Shared Requirements (Non-Negotiables)
• Operates with a partner mindset, not an employee mindset.
• High autonomy, ownership, and long-term orientation.
• Comfortable in ambiguity and fast-changing environments.
• Clear communicator with strong judgment.
• Interested in long-term alignment (2–5 year horizon), not short-term gigs.
• Drawn to experimentation, learning, and building meaningful systems.

Benefits

• Commission: 5%+ on new revenue generated through systems you help build
• Upside: Significant earning potential tied to business growth and high-ticket clients
• USD Salary
• Ability to work remotely.