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.
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
