**Senior AI & Systems Lead**:**Location**: Fully Remote**Availability**: Full-time, strong overlap with PST business hours**Reports to**: CEO**Works closely with**: Executive team, Department Leads and Portfolio Startups**Compensation**: Competitive base + performance bonuses tied to output, leverage, and top-line impact**PLEASE READ BEFORE APPLYING****Applications submitted elsewhere will not be considered.
**:**About the role**: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.
**Who You Are**:You are someone who doesn't treat AI as a tool, you treat it as the default way work gets done.You're systems-obsessed and relentless about leverage, integrations, automation, and speed.You're **deeply fluent in modern AI tooling**— ChatGPT, Claude, Perplexity, Manus, **Lovable**, and Zapier/Make — not experimenting, _shipping_.You architect and build AI-powered systems that directly support the executive office and extend across the company's startups and investments.You design systems that power core business functions across marketing, operations, and finance in fast-moving, high-growth environments (without hand-holding).
**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.If something relies on memory, follow-ups, or heroics, its broken — and you're here to fix it.
**What You'll Do**:**1.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**2.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**3.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**4.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**5.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**6.Experimentation, Innovation & Scale**- Aggressively exp

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