Chief of Staff (Sydney) - AI Expert

Chief of Staff / Business Operations Associate

Location: Sydney (with flexibility)
Reporting to: CEO

The Role

This is not a traditional PA role.

You’ll work directly with the CEO to solve high-impact business problems across strategy, operations, and growth. One minute you might be researching international tax implications, the next you’re speaking with major event organisers, and later analysing investment opportunities.

If you like variety, autonomy, and being thrown into the deep end — you’ll enjoy this. If you need structure and step-by-step instructions, you won’t.

What You’ll Be Doing

• Acting as a force multiplier for the CEO — extending decision-making and execution capacity
• Researching and breaking down complex topics (e.g. international markets, tax systems, new industries)
• Communicating with senior stakeholders (clients, partners, suppliers) with confidence and clarity
• Preparing briefs, recommendations, and action plans — not just summaries
• Identifying opportunities across the business (growth, efficiency, partnerships)
• Supporting key projects from idea through to execution
• Analysing commercial opportunities such as new markets or investments
• Bringing structure to ambiguous problems and driving them forward

What We’re Looking For

We don’t care if your title was “PA”.

We care how you think.

You might come from:

• Consulting
• A startup or high-growth business
• A business/strategy/operations role
• Or be an exceptional graduate with strong commercial thinking

What matters:

• Sharp problem-solving ability — you can break down unfamiliar problems quickly
• Commercial awareness — you understand how businesses make money and make decisions
• Strong communication — you can speak with senior stakeholders and hold your own
• High ownership — you don’t wait to be told what to do
• Curiosity — you enjoy learning new industries, fast
• Execution bias — you don’t just analyse, you move things forward

What This Role Is Not

• It’s not diary management and booking flights (though you may occasionally handle logistics)
• It’s not a task-only admin role
• It’s not structured or predictable

Why This Role Exists

The CEO is involved across multiple areas of the business and needs someone who can:

• Think independently
• Take ownership of problems
• Operate at a high level across different domains

Done well, this role becomes a pathway into senior leadership.

How to Apply

Submit your CV along with a short response (max 1 page) to the following:

1. We are considering expanding into Dubai. What are 3 key things you would investigate first, and why?
2. A major event organiser (e.g. Tennis Australia) is planning a large pavilion. What would they care about most?
3. If you had $500k to invest in property today, what would you look for?

We’re not looking for perfect answers — we’re looking at how you think.

Final Note

If you’re looking for a clearly defined role with predictable tasks, this isn’t it.

If you want exposure to real business decisions and the chance to accelerate your career — apply.