Operations Manager and Chief of Staff to the Founder (AI-First)

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.

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Operations leadership

Coordinate the content and client success teams under the Founder's direction, growing into full ownership and management of both as trust builds

Set the operating rhythm. Chase deliverables, track client health, escalate issues, ensure SLAs are met

Run the operational backbone so the Founder can focus on growth

Track and flag operational issues before they reach the Founder's desk

Drive the rollout of new tools, processes, and team initiatives

Process improvement and systemisation (a core deliverable)
This is one of the highest-value parts of the role. You will:

Shadow and observe how the Founder and the teams spend their time, week by week

Map every recurring task, decision point, and workflow across sales, recruiting, ops, content, client success, and finance admin

Document each one as a clear, repeatable SOP, including triggers, steps, tools used, decision criteria, and handoff points

Build a central SOP library that is searchable, maintained, and version-controlled

Apply process-improvement principles (Six Sigma, Lean, or equivalent) to identify waste, reduce variation, cut cycle time, and improve quality

Measure before and after. Show the numbers

Identify which workflows can be delegated or automated with AI agents

Turn the business from a set of habits living in the Founder's head into a documented, measurable system

The benchmark: within six months, any new hire should be able to pick up an SOP and execute the task without needing to ask the Founder how it works.

Direct founder support (the operational cockpit)

Manage the Founder's inbox across Outsourced Staff and Conversational AI. Triage, draft replies, send under direction, escalate what needs his eyes

Run his calendar. Book meetings, defend his focus time, send reminders, prep him for what's next

Attend meetings with the Founder. Take notes, capture decisions and actions, own the follow-through

Daily and weekly check-ins covering priorities, deals in motion, follow-ups due, and blockers

Velocity and client responsiveness

Post-meeting summaries drafted and sent within one to two hours of a call ending

Sales proposals drafted and sent the same day if a request comes through before noon

Follow up warm leads by phone when they go quiet. Typically five calls per week. ("Dom sent that proposal, where are you at?")

Keep HubSpot hygienically moving. Update deal stages, log activity, flag stale deals, ensure leads are in follow-up sequences

Pull together pre-call briefs so the Founder walks into every meeting prepared

AI-leveraged delivery (support and training provided)

Default to Claude as your primary AI tool. Training will be provided on Claude, Claude Projects, prompt engineering, and the internal AI stack

Use AI to draft, summarise, research, and prep faster on everything you touch

Build and maintain light agents and automations under the Founder's direction

Spot repetitive tasks and propose an AI-assisted way to handle them

Must haves

5+ years in operations, with real experience supporting a founder, CEO, or business owner directly

Background in an outsourcing, BPO, or support services business. You understand how service delivery actually works behind the scenes

Formal process-improvement certification (Six Sigma Green or Black Belt, Lean, or equivalent) AND a track record of running initiatives that moved measurable numbers (cycle time, defect rate, cost, SLA performance)

A genuine systems thinker. You see a messy workflow and instinctively want to document, measure, and improve it

200% into AI. Genuinely fascinated, actively learning, and excited to spend a chunk of your week building and refining AI workflows. (We provide the training. You bring the hunger.)

Experience coordinating or managing teams, with the appetite to take full ownership of them

Confident across Google Workspace, HubSpot, and Loom

Strong written and spoken English. You can match the Founder's tone in his emails and hold your own on a call or in a meeting

Comfortable picking up the phone and making warm follow-up calls without being pushed

Sharp judgement on what needs the Founder's attention now, what can wait, and what you can handle yourself

Proactive. You finish things, you do not just flag them

Calm under pressure and comfortable with the pace of a founder-led business

Able to work AU business hours (AEST, 9:00 AM to 6:00 PM) on the Australian public holiday calendar

Reliable high-speed internet and a professional dual-monitor home office setup

Nice to haves

Australian client experience

Hands-on experience with Claude specifically (not just ChatGPT)

Experience building custom GPTs, Claude Projects, or simple automations

ZoomInfo or Expandi exposure (our outbound team handles these, so not essential)

Experience drafting sales proposals or running follow-up sequences

Prior experience holding full P&L or team-leadership responsibility

Logistics

Full-time, AU business hours (AEST, 9:00 AM to 6:00 PM)

Follows the Australian public holiday calendar, not the Philippines calendar

Occasional out-of-hours availability for time-sensitive work

Reliable high-speed internet and a professional dual-monitor home office setup

Long-term role with a clear path into full operational leadership

\n₱80,000 - ₱150,000 a month
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