Senior AI & Systems Lead

Trolley • San Juan, PR

23h • Remote

About The Position

This isn't an automation role, automation is table stakes. This role exists to make AI the default operating layer of the business and build systems that materially improve how the team thinks, executes, and decides. The Senior AI & Systems Lead is embedded in the executive office and works directly with the CEO to modernize and optimize how the business operates, enabling leadership with best-in-class systems that scale across the organization. This is a high-impact, hands-on role . Strategy matters, but execution is non-negotiable. The person in this role sets the direction and builds the systems themselves. Were a fast-moving team that experiments aggressively, and ships consistently.

Requirements

• Proven AI systems operator — you've shipped LLM-powered workflows using tools like ChatGPT/OpenAI, Claude, Perplexity, Manus, Lovable, Zapier/Make
• AI-stack generalist — fluent across multiple LLM environments (Claude Code, CodeX, OpenClaw, OpenAI ecosystem), selecting the right tool per use case
• Systems-first thinker — you design workflows, data flows, and leverage layers, not one-off automations
• ClickUp power user + vibe coder — you build fast, wire tools together, and turn ideas into working systems without heavy engineering
• High-agency executor — extreme ownership, startup-caliber speed, thrives under ambiguity and pressure
• Deeply embedded in the AI ecosystem — you follow builders, read Substacks, track X accounts, and stay ahead of tooling shifts

Responsibilities

• Executive Office Systems & Leverage Design and maintain the operating systems that power the CEO and executive office, using best-in-class tools
• Translate fragmented, unstructured inputs (from calls, documents, materials) into durable workflows and execution models
• Continuously audit CEOs time, workflows, decisions, content, and execution output for inefficiencies
• Eliminate low-leverage work through AI, automation, and system design
• Ensure leadership operates inside systems, not memory or manual follow-ups
• AI, Automation & Tooling Architect and build AI-first workflows using LLMs, Claude Code, CodeX, OpenClaw, agents, automations, and integrations — with fluency across multiple AI stacks from day one.
• Rapidly prototype, ship, and iterate relying on strong vibe-coding proficiency
• Use AI to build custom presentations, spreadsheets, and internal tools that support executive decision-making
• Translate complex, scattered data into usable AI workflows and logic
• Continuously evaluate and propose AI tools based on leverage, usability, and system fit
• Data, Knowledge & Information Architecture Design systems that extract, clean, structure, and persist operational data for AI consumption
• Integrate data sources across internal tools, meeting transcripts and status updates into a single system of truth to close internal gaps
• Organize Google Drives and executive documentation into AI-ready knowledge bases
• Build scalable knowledge architectures across the company and its startups
• Maintain data quality so decisions reflect reality, not vibes
• ClickUp Ownership, Governance & Adoption Own ClickUp end-to-end as the execution backbone (architecture, automations, reporting, and visibility)
• Design and maintain ClickUp spaces, workflows, dashboards, and views for executives and across teams
• Ensure ClickUp is used correctly and consistently across the organization. No shadow systems, no work happening off-platform
• Train, enable, and hold teams accountable for proper system usage and autonomous execution
• Eliminate micromanagement and ambiguity around ownership, status, and blockers through clean workflows
• AI-Powered Analysis, Reporting & Visibility Build AI-driven analysis workflows (weekly rollups, blocker detection, execution signals)
• Replace manual reporting with automated insight generation
• Surface patterns, risks, and opportunities to leadership through AI-powered solutions before they become problems
• Ensure leadership has real-time visibility into execution, growth, and performance without status chasing, but through system oversight
• Systemize content marketing reporting, analytics dashboards, and performance visibility
• Experimentation, Innovation & Scale Aggressively experiment with new AI tools, agents, and architectures
• Ship fast, test fast and ship what works
• Define and enforce clear system usage standards — adoption is non-negotiable
• Redesign processes to move work from people to systems and increase execution velocity
• Define which decisions belong in systems versus people, progressively removing low-impact decisions from humans

Benefits

• Work from anywhere
• Flexible schedule and time off — no micromanaging
• Direct collaboration with the Founder
• Access to top-tier AI tools (Perplexity, ChatGPT, ClickUp Brain and more)
• Clear path for long term career growth
• A supportive company culture grounded in ownership and prioritizing progress over perfection

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed