Senior Ai & Systems Lead (Xico)

Senior Ai & Systems Lead (Xico)

06 abr
|
Trolley
|
Xico

06 abr

Trolley

Xico

Senior AI &Systems; Lead

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Location: Fully RemoteAvailability: Full-time, strong overlap with PST business hoursReports to: CEOWorks closely with: Executive team, Department Leads and Portfolio StartupsCompensation: Competitive base + performance bonuses tied to output, leverage, and top-line impact

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PLEASE READ BEFORE APPLYINGWe are only reviewing candidates who submit their application through this link: submitted elsewhere will not be considered.

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About the role

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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.

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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.

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This is a high-impact, hands-on role.

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Strategy matters, but execution is non-negotiable.

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The person in this role sets the direction and builds the systems themselves.

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Were a fast-moving team that experiments aggressively, and ships consistently.

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Who You Are

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You are someone who doesn't treat AI as a tool, you treat it as the default way work gets done.

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You're systems-obsessed and relentless about leverage, integrations, automation, and speed.

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You're deeply fluent in modern AI tooling — ChatGPT, Claude, Perplexity, Manus, Lovable, and Zapier/Make — not experimenting, shipping.

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You architect and build AI-powered systems that directly support the executive office and extend across the company's startups and investments.

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You design systems that power core business functions across marketing, operations, and finance in fast-moving,



high-growth environments (without hand-holding).

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Your goal is simple: eliminate manual work and fragmented context by moving execution and decision-making into AI-first systems that scale across the company, enforce clean data, accelerate decisions, and multiply executive leverage.You push systems before you're asked.

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If something relies on memory, follow-ups, or heroics, its broken — and you're here to fix it.

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What You'll Do

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- Executive Office Systems & Leverage

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Design and maintain the operating systems that power the CEO and executive office, using best-in-class tools

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Translate fragmented, unstructured inputs (from calls, documents, materials) into durable workflows and execution models

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Continuously audit CEOs time, workflows, decisions, content, and execution output for inefficiencies

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Eliminate low-leverage work through AI, automation, and system design

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Ensure leadership operates inside systems, not memory or manual follow-ups

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- AI, Automation & Tooling

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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.

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Rapidly prototype, ship, and iterate relying on strong vibe-coding proficiency

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Use AI to build custom presentations, spreadsheets,



and internal tools that support executive decision-making

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Translate complex, scattered data into usable AI workflows and logic

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Continuously evaluate and propose AI tools based on leverage, usability, and system fit

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- Data, Knowledge & Information Architecture

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Design systems that extract, clean, structure, and persist operational data for AI consumption

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Integrate data sources across internal tools, meeting transcripts and status updates into a single system of truth to close internal gaps

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Organize Google Drives and executive documentation into AI-ready knowledge bases

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Build scalable knowledge architectures across the company and its startups

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Maintain data quality so decisions reflect reality, not vibes

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- ClickUp Ownership, Governance & Adoption

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Own ClickUp end-to-end as the execution backbone (architecture, automations, reporting, and visibility)

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Design and maintain ClickUp spaces, workflows, dashboards, and views for executives and across teams

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Ensure ClickUp is used correctly and consistently across the organization.

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No shadow systems, no work happening off-platform

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Train, enable, and hold teams accountable for proper system usage and autonomous execution

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Eliminate micromanagement and ambiguity around ownership, status, and blockers through clean workflows

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- AI-Powered Analysis, Reporting & Visibility

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Build AI-driven analysis workflows (weekly rollups, blocker detection, execution signals)

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Replace manual reporting with automated insight generation

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Surface patterns, risks, and opportunities to leadership through AI-powered solutions before they become problems

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Ensure leadership has real

📌 Senior Ai & Systems Lead (Xico)
🏢 Trolley
📍 Xico

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