Senior AI & Systems Lead

Role

The Senior AI & Systems Lead partners directly with the CEO and executive team to modernize and operationalize AI-first systems that scale across the company and its portfolio startups. This is a hands-on role responsible for both strategy and executing end-to-end systems that replace manual work and improve decision-making, execution, and visibility.

Key Responsibilities

• Design and maintain executive office operating systems that power the CEO and leadership team.
• Translate fragmented inputs (calls, documents, materials) into durable workflows and execution models.
• Continuously audit executive time, workflows, decisions, content, and execution output for inefficiencies and remove low-leverage work.
• Architect and build AI-first workflows using LLMs, Claude Code, CodeX, OpenClaw, OpenAI tools, agents, automations, and integrations.
• Rapidly prototype, ship, and iterate; rely on strong vibe-coding proficiency to wire tools together.
• Use AI to produce custom presentations, spreadsheets, internal tools, and automated insight generation for executive decision-making.
• Design systems to extract, clean, structure, and persist operational data for AI consumption; integrate meeting transcripts and status updates into a single system of truth.
• Own ClickUp end-to-end: architecture, automations, reporting, spaces, dashboards, views, governance, adoption, and training.
• Build AI-driven analysis workflows (weekly rollups, blocker detection, execution signals) and replace manual reporting with automated insights.
• Aggressively experiment with new AI tools and agents; define and enforce system usage standards and adoption.

Requirements

• Proven track record as an AI systems operator with shipped LLM-powered workflows using tools such as ChatGPT/OpenAI, Claude, Perplexity, Manus, Lovable, Zapier/Make.
• AI-stack generalist: fluent across multiple LLM environments (e.g., Claude Code, CodeX, OpenClaw, OpenAI ecosystem) and able to select the right tool per use case.
• Systems-first thinker who designs workflows, data flows, and leverage layers rather than one-off automations.
• ClickUp power user with strong governance, automation, and architecture experience.
• High-agency executor with startup-caliber speed; comfortable with ambiguity and full ownership.
• Strong cross-functional collaboration, training, and enablement skills to drive consistent usage across teams and eliminate shadow systems.

Tools & Tech Mentioned

• ChatGPT / OpenAI
• Claude (and Claude Code)
• Perplexity
• Manus
• Lovable
• Zapier
• Make
• CodeX
• OpenClaw
• ClickUp (including ClickUp Brain)
• Google Drive

Success Metrics

• CEO and executive office operate entirely inside best-in-class, AI-first systems.
• Executive time, decisions, and output are continuously audited and optimized.
• Company scales without added meetings, coordination, or headcount; manual follow-ups eliminated.
• Real-time visibility into execution and performance via systems, not manual reporting.
• Autonomous progress inside defined workflows with enforced ownership and clear priorities.

Location & Logistics

• Fully remote; full-time with strong overlap required with PST business hours.
• Reports to the CEO and works closely with executive team, department leads, and portfolio startups.

Compensation & Perks (summary)

• Competitive base plus performance bonuses tied to output and top-line impact.