Senior AI & Systems Lead

Role

The Senior AI & Systems Lead embeds in the executive office and partners with the CEO to design, build, and operate AI-first systems that scale across the company and its startups. This is a high-impact, hands-on role focused on execution: designing operational workflows, integrating data sources, and shipping LLM-powered automation and tooling that materially improve how leadership operates.

Key Responsibilities

• Design and maintain executive office operating systems, turning fragmented inputs (calls, documents, notes) into durable workflows and execution models.
• Architect and build AI-first workflows and automations using LLMs, agents, and integrations; rapidly prototype, ship, and iterate.
• Extract, clean, structure, and persist operational data and knowledge to power AI consumption and decision-making.
• Own ClickUp end-to-end as the execution backbone: architecture, spaces, automations, dashboards, governance, and adoption.
• Build AI-driven analysis and reporting workflows (weekly rollups, blocker detection, execution signals) to replace manual reporting with automated insights.
• Experiment aggressively with new AI tools and agents, define system usage standards, and scale successful patterns across the organization.

Requirements

• Proven operator who has shipped LLM-powered workflows and AI integrations in production.
• Fluency across multiple AI stacks and tools (e.g., ChatGPT/OpenAI, Claude, Perplexity, Manus, Lovable, Zapier/Make) and familiarity with agent architectures and code-like LLM tools (Claude Code, CodeX, OpenClaw).
• Systems-first thinker with strong information architecture and data-quality focus; able to design workflows, data flows, and leverage layers rather than one-off automations.
• ClickUp power user with experience building automations, dashboards, and enforcing platform governance and adoption.
• High-agency executor who moves quickly, ships iteratively, and thrives under ambiguity and pressure.
• Strong stakeholder collaboration, training, and enablement skills to drive consistent usage and accountability across teams.

Success Criteria

• CEO and executive team operate inside best-in-class, AI-first systems with reduced manual follow-ups and meetings.
• Executive time, decisions, and outputs are continuously audited and optimized by systems.
• Company scales execution without proportional increases in meetings or headcount; systems provide real-time visibility and autonomous progress.

What We Offer (Selected)

• Fully remote, work-from-anywhere arrangement with flexible schedule and time off.
• Direct collaboration with the founder/CEO and access to top-tier AI tools (Perplexity, ChatGPT, ClickUp Brain, etc.).
• Competitive base compensation plus performance bonuses tied to output and impact.
• Clear path for long-term career growth and a culture oriented to ownership and rapid execution.