Senior AI
Solliciteren
Plaats
Sint-Jans-Molenbeek1080
Brussel
België
Contract
Vooltijds, Onbepaalde duurDatum gepubliceerd
2026-02-21Online to:
2026-04-22EUR 20.00 HOUR
Senior AI
- Trolley AI
- Brussel
- 4 dagen geleden
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
PLEASE READ BEFORE APPLYING
We are only reviewing candidates who submit their application through this link:
Applications submitted elsewhere will not be considered.
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.
Were 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 — 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.
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.
Its 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. 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
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
PLEASE READ BEFORE APPLYING
We are only reviewing candidates who submit their application through this link:
Applications submitted elsewhere will not be considered.
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.
Were 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 — 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.
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.
Its 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. 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
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