Operations Manager and Chief of Staff to the Founder (AI-First)
Outsourcedstaff
·May 23, 2026
- Salary
- $80k – $150k/mo
- Location
- Philippines
- Workplace
- Remote
- Type
- Full-time
- Department
- Management / Executive
- Seniority
- Senior
- Source
- Lever
Description
Operations Manager and Chief of Staff to the Founder (AI-First)
About Outsourced Staff
Outsourced Staff is an Australian-owned offshore staffing company. We help Australian, NZ, and US businesses build reliable, high-performing teams in the Philippines across operations, sales, recruiting, finance, and technical functions. Alongside Outsourced Staff, the Founder also leads Conversational AI, a sister business delivering AI Receptionist, Customer Service, and Sales Agent solutions.
We run a hybrid AI plus human model. Our people use AI tools every day to move faster, think clearer, and deliver more.
About the Role
This is a senior operations role and direct support to the Founder, rolled into one. You will run the operational backbone of the business while acting as the Founder's right hand. His operational brain outside his head. His filter, his follow-through, his force multiplier.
You will start by coordinating the content and client success teams under the Founder's direction. As trust builds, you will take full ownership and run them. This is a genuine leadership arc, not a static support role. You will own the systemisation of every recurring workflow in the business, drive velocity on client-facing deliverables, and make sure that what the Founder commits to actually lands.
You will be expected to use Claude as your default AI working layer, with ChatGPT and other tools alongside it. Full training on Claude, prompt engineering, Claude Projects, and our internal AI workflows will be provided. You do not need to arrive as an AI expert. You do need to be 200% into AI. Genuinely fascinated, actively learning, excited to spend a chunk of your week building and refining AI workflows. If AI bores you, this role is not for you.
You think in systems. You hold a process-improvement discipline (Six Sigma, Lean, or equivalent) and you've run real initiatives that moved real numbers. You will turn a fast-moving, founder-led business into a documented, measurable, scalable operation.
You will sit in meetings with the Founder, you will be client-facing when needed, and you're happy to pick up the phone and follow up a prospect. You understand that how fast and how cleanly we respond is part of how we compete.