Senior AI & Systems Lead

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

About the Role

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.

Who You Are

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 — 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.

What You'll Do

1. Executive Office Systems & Leverage

• 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 CEOs 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, OpenClaw, 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

3. Data, Knowledge & Information Architecture

• 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
• Maintain data quality so decisions reflect reality, not vibes

4. ClickUp Ownership, Governance & Adoption

• Own ClickUp end-to-end as the execution backbone (architecture, automations, reporting, and visibility)
• Design and maintain ClickUp spaces, workflows, dashboards, and views for executives and across teams
• Ensure ClickUp 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, and opportunities to leadership through AI-powered solutions before they become problems
• Ensure leadership has real-time visibility into execution, growth, and performance without status chasing, but through system oversight
• Systemize content marketing reporting, analytics dashboards, and performance visibility

6. Experimentation, Innovation & Scale

• Aggressively experiment with new AI tools, agents, and architectures
• Ship fast, test fast and ship what works
• Define and enforce clear system usage standards — adoption is non-negotiable
• Redesign processes to move work from people to systems and increase execution velocity
• Define which decisions belong in systems versus people, progressively removing low-impact decisions from humans

What You Bring

• Proven AI systems operator — you've shipped LLM-powered workflows using tools like

  ChatGPT/OpenAI, Claude, Perplexity, Manus, Lovable, Zapier/Make
• AI-stack generalist — fluent across multiple LLM environments (Claude Code, CodeX, OpenClaw, OpenAI ecosystem), selecting the right tool per use case
• Systems-first thinker — you design workflows, data flows, and leverage layers, not one-off automations
• ClickUp power user + vibe coder — you build fast, wire tools together, and turn ideas into working systems without heavy engineering
• High-agency executor — extreme ownership, startup-caliber speed, thrives under ambiguity and pressure
• Deeply embedded in the AI ecosystem — you follow builders, read Substacks, track X accounts, and stay ahead of tooling shifts

This Role Is Not For You If

• You're early-career or still learning the fundamentals
• You want a narrow scope, clear lanes, or a static job description
• You need permission, hand-holding, or step-by-step direction
• You prefer planning or theory over shipping real systems
• You're looking for a support role instead of full ownership
• You're impressed by basic automation or surface-level AI

What Success Looks Like

Most companies talk about AI and then move at a glacial pace. This team is already operating AI-first, and wants someone to push it further. You'll be successful if:

• The CEO operates entirely inside best-in-class, AI-first systems
• Executive time, decisions, and output are continuously audited and optimized
• The company scales without added meetings, coordination, or headcount
• Systems replace unnecessary follow-ups, and manual coordination
• Systems provide real-time visibility without manual updates or reporting
• Work progresses autonomously inside defined workflows
• Ownership, priorities, and dependencies are enforced by systems

Your work will directly shape how the executive office, leadership team, and portfolio companies operate, setting them up to run as efficiently as possible.

This role isn't about maintaining systems. It's about building the operating layer that multiplies executive leverage, sharpens decision-making, and makes the company faster, smarter, and harder to compete with.

About Us

Who We Are Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated powerhouse—combining strategy, design, production, and performance analysis to deliver world-class results.

AI Mindset & Continuous Innovation Our team works with an AI-first mindset, and we look for people who are genuinely excited about using technology to make their work faster, smarter, and more creative.