Senior AI

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

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.

Were a fast-moving team that experiments aggressively, and ships consistently.

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 — ChatGPT, Claude, Perplexity, Manus, Lovable, and Zapier/Make — 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, its broken — and you're here to fix it.

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

• 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

• 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

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.
Its about building the operating layer that multiplies executive leverage, sharpens decision-making, and makes the company faster, smarter, and harder to compete with.

----

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. Everyone at Trolley integrates AI into their daily work, and we expect new team members to contribute to this culture of curiosity, experimentation, and continuous improvement.

We Operate Under Founder Mode
Trolley is built on a Founder Mode mindset—an operating system rooted in ownership, strategic thinking, and execution at speed. Here, we look for people who take initiative, think like entrepreneurs, and use tools like AI to optimize how work gets done. But Founder Mode isnt about going it alone—its about working within high-trust, collaborative teams where contribution matters more than control. We value creativity, resourcefulness, and clear communication. If youre driven by impact, thrive in dynamic environments, and believe in scaling through systems, not stress—this is the place for you.

Benefits at Trolley
At Trolley, we believe in building a company that works for you — not the other way around. That means freedom, tools, and culture that support both your creativity and your execution. We offer:

• Work from anywhere
• Flexible schedule and time off — no micromanaging
• Direct collaboration with the Founder
• Access to top-tier AI tools (Perplexity, ChatGPT, ClickUp Brain and more)
• Clear path for long term career growth
• A supportive company culture grounded in ownership and prioritizing progress over perfection

For any questions regarding the role, please email us