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

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.

We're a fast-moving team that experiments aggressively and ships consistently.

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, it's broken — and you're here to fix it.

• 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 CEO's 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, Open Claw, 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
• 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

4. Click Up Ownership, Governance & Adoption

• Own Click Up end-to-end as the execution backbone (architecture, automations, reporting, and visibility)
• Design and maintain Click Up spaces, workflows, dashboards, and views for executives and across teams
• Ensure Click Up 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,…