AI Chief of Staff
AI Chief of Staff (Founding Role, 90-Day Trial → Full-Time)
Stark Carpet | New York / Hybrid
Paid, full-time, trial-to-hire
Build real AI systems inside a real company—fast. This is not an internship. It’s a rare, high-trust role designed for someone early in their career who learns fastest by doing, not watching.
About Stark Carpet
Stark Carpet is a third-generation, family-owned luxury carpet and rug company with an 85+ year legacy and $200M+ in annual revenue. We work with the world’s top interior designers and operate a complex, real-world business with showrooms, manufacturing partners, logistics, and long-tenured teams.
We’re beginning to transform Stark into an AI-native organization—not a startup, but a real operating company using AI to:
- Make work easier
- Remove friction and busywork
- Increase speed and clarity
- Help people do higher-value thinking
This is a core company priority, led directly by the CEO.
The Role: AI Chief of Staff (Founding)
You’ll work directly with the CEO to prove what’s possible with AI inside a legacy organization. Your job is not research, decks, or demos. It is to build working systems that people actually use.
You will:
- Identify repetitive, high-friction work
- Build AI agents and automations
- Reduce cognitive load for leaders and teams
- Increase speed and clarity across real workflows
You won’t be handed a roadmap. You’ll create one—by building.
Why This Role Is Special (Especially Early Career)
- Direct exposure to executive decision-making
- Real ownership from Day 1
- No “shadowing” or fake projects
- Freedom to experiment with modern AI tools
- Learning compressed into weeks, not years
This role is designed to accelerate your growth faster than almost any traditional early-career job.
What You’ll Do
🔍 Find Problems Worth Solving
- Shadow executives and managers
- Identify repetitive or confusing work
- Look for tasks that slow decisions or drain energy
🤖 Build AI Agents & Automations
- Create special-purpose AI agents (intern → analyst level)
- Automate workflows like:
- Meetings → notes → follow-ups
- Reporting and data retrieval
- Knowledge capture and internal communication
- Use modern tools (Zapier/Make, LLMs, Cursor, voice tools, etc.)
🚀 Ship, Learn, Iterate
- Launch quickly
- Improve weekly
- Kill what doesn’t work
- Document what does
🎓 Teach by Showing
- Demo what you build
- Help leaders learn how to work with AI agents
- Normalize experimentation across teams
What Success Looks Like (By Day 90)
- AI agents built or in active use
- Multiple workflows meaningfully automated
- Leaders say: “I can’t imagine doing this the old way.”
AI shifts from curiosity → conviction inside the company
If that happens, this becomes a full-time leadership role.
Who You Are
You might be a great fit if you:
- Learn fastest by building and experimenting
- Are comfortable with ambiguity
- Like figuring things out without step-by-step instructions
- Are curious about AI, automation, and systems
- Can communicate clearly and take feedback
- Are excited by real responsibility early in your career
You do not need:
- A CS degree
- Prior “Chief of Staff” experience
- Enterprise background
- Mindset matters more than pedigree.
The 90-Day Trial (Why This Is a Feature)
The trial is intentional and fair. It lets you quickly see if:
- You enjoy real ownership
- You like working directly with a CEO
- You thrive in a fast, FAFO (“figure it out”) environment
- If it’s a fit → we go all-in. If not → you leave with real experience, references, and respect.
How to Apply
Please include:
- A short note on why this role excites you
- Examples of things you’ve built, automated, or experimented with (school, work, or personal)
Final Note
This role is not about predicting the future of AI. It’s about building it, here, with urgency, humility, and results.