Senior AI & Systems Lead

The Mission This isn’t an automation role—basic automation is table stakes. This role exists to make AI the default operating layer of our business and build systems that materially improve how our team thinks, executes, and decides.

As the Senior Automations & AI Systems Lead, you will be embedded directly within the executive office. Working alongside the CEO, you will modernize and optimize how the business operates, enabling leadership with best-in-class systems that scale across the entire organization. This is a high-impact, hands-on role. Strategy matters, but execution is non-negotiable; you will set the direction and build the systems yourself.

Our Culture We are a fast-growing creative operations company delivering high-impact digital and marketing solutions. We operate with an AI-first mindset and a Founder Mode philosophy—focusing on extreme ownership, strategic thinking, and relentless execution velocity. We value creativity, resourcefulness, and clear communication. If you thrive in dynamic environments and believe in scaling through systems rather than headcount, you will fit right in.

Responsibilities

1. Executive Office Systems & Leverage

Design and maintain the core operating systems that power the CEO and executive office.

Translate fragmented, unstructured inputs (from calls, documents, and meetings) into durable workflows and execution models.

Continuously audit the CEO’s time, workflows, decisions, and content output to eliminate inefficiencies and low-leverage work.

Ensure leadership operates strictly inside systems, eliminating reliance on memory or manual follow-ups.

1. AI, Automation & Tooling Architecture

Architect and build AI-first workflows using LLMs, agents, automations, and integrations from day one.

Rapidly prototype, ship, and iterate custom internal tools, presentations, and spreadsheets to support executive decision-making.

Translate complex, scattered data into usable AI workflows and logic.

Continuously evaluate emerging AI tools based on leverage, usability, and system fit.

1. Data, Knowledge & Information Architecture

Design systems that extract, clean, structure, and persist operational data for AI consumption.

Integrate disparate data sources (internal tools, meeting transcripts, status updates) into a single system of truth.

Organize documentation and cloud storage into highly structured, AI-ready knowledge bases across the company and its startups.

Maintain rigorous data quality to ensure executive decisions reflect reality, not "vibes."

1. ClickUp Ownership, Governance & Adoption

Own ClickUp end-to-end as the company's central execution backbone (architecture, automations, reporting, and visibility).

Design and maintain spaces, workflows, dashboards, and views for executives and cross-functional teams.

Enforce platform compliance across the organization to eliminate shadow systems and off-platform work.

Train and hold teams accountable for proper system usage to eliminate micromanagement and ambiguity.

1. AI-Powered Analysis & Reporting

Build automated analysis workflows, including weekly rollups, blocker detection, and execution signals.

Replace manual reporting with automated, AI-driven insight generation.

Surface operational patterns, risks, and opportunities to leadership before they become blockers.

Systemize content marketing reporting and analytics dashboards for real-time visibility.

• You are not early-career or still learning the fundamentals. You are a proven operator who treats AI as the default way work gets done.
• You design comprehensive workflows, data flows, and leverage layers rather than fragmented, one-off automations.
• Deep expertise in ClickUp architecture, advanced automations, reporting dashboards, and workspace governance.
• Proven experience shipping real-world workflows using tools like ChatGPT/OpenAI, Claude, Perplexity, and Zapier/Make.
• Extreme ownership, startup-caliber speed, and the ability to thrive under ambiguity without needing step-by-step direction or hand-holding.
• You value shipping real, functional systems over planning, theory, or strategy decks.

• Experience or active experimentation with next-generation AI tools and frameworks such as Manus, Lovable, Claude Code, CodeX, or OpenClaw.
• The ability to rapidly wire tools together, prototype fast, and turn abstract ideas into working systems without heavy traditional engineering constraints.
• Prior experience building and scaling knowledge architectures across decentralized environments, such as venture studios, portfolio startups, or multi-client operations.

• Claude, ChatGPT, Perplexity, Zapier/Make, ClickUp, and modern LLM stacks (CodeX, OpenClaw); ability to prototype and integrate across Google Workspace, APIs, and custom AI workflows.