Senior AI & Systems Lead
Explicitly requires vibe-coding proficiency and rapid prototyping with AI tools; uses ChatGPT/Claude/Perplexity/Manus/Lovable and Zapier/Make alongside ClickUp to ship AI-first workflows.
About the Role
Senior AI & Systems Lead embedded in the executive office to make AI the default operating layer of the business by designing, building, and operating AI-first systems that increase executive leverage, eliminate manual work, and scale across the company's startups. Remote, full-time role reporting to the CEO with ownership of ClickUp, AI workflows, data/knowledge architecture, and automation.
Job Description
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.