Chief of Staff

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Brief overview of this role:

• Reports to: CEO

• Level: Open, depending on experience

• Location: Sydney

• Remuneration: A$180,000 - A$240,000 (excl. Super), depending on experience

🏢 About Sitemate

Sitemate builds best-in-class software and AI agents for the built world, helping construction, infrastructure and industrial companies work smarter and faster. Our mission is to multiply the engineering power of the built world.

Storm is the #1 data capture agent for the front line of the built world - converting audio, photos and videos into clean structured records.

With conversational support in-app and across SMS, Whatsapp and phone calls, Storm is shifting front line workers from paperwork and clunky digital forms, to natural language and multi-channel data capture.

Our core platforms are Dashpivot (safety, quality and field reporting), Gearbelt (fleet and asset management), Flowsite (no-code integrations), and the Sitemate mobile app for every worker on site.

We have strong product-market fit, generating thousands of new leads per month through word of mouth and organic channels. We are backed by Blackbird, with 200 people across 18+ countries and entities in Australia, the UK, the US and Canada.

🚀 Why this role exists now

Sitemate runs across multiple products, regions and functions, and AI is changing how work gets done in every one of them. The CEO's priorities cut across all of it.

This role turns those priorities into initiatives that ship. Each one gets a clear owner, a date, and its dependencies and risks surfaced early. The role also owns the operating cadence and reporting the leadership team and board run on, built with AI from day one.

The role is also Sitemate's operational lead. Legal Ops, AI Ops, People Ops, Exec Ops and Finance all run through this seat, and you own the initiatives that get our operational infrastructure ready for the next stage of growth. AI Ops brings RevOps, GTM Ops and BizOps together, and we're making each of them AI-native, with coding agents taking on more of the work so the team can focus on what needs judgement.

From day one, you take over the running of Legal Ops, AI Ops, People Ops, Exec Ops and Finance. What you shape next is the set of initiatives that gets them ready for the next stage of growth, and you'll define those initiatives yourself.

📝 The role

The Chief of Staff is a force multiplier for the CEO. You run the CEO's operating cadence and see cross-functional priorities through to delivery. You prepare the CEO's decisions and communications, and hold every department to what it committed. You also lead operations across the business, owning the initiatives that prepare it to scale.

This is a hands-on role. You write the brief, build the tracker, set up the agent and chase the follow-through yourself. You also lead the operational team as a player-coach, doing the work alongside them.

The role has looked different at Sitemate over the years, leaning towards GTM in one version and Engineering, Product and Design in another. This version is operationally focused, and it can lead into COO or VP-level roles.

🎯 What you own

1. The CEO's priorities, run as a programme. You map goals, dependencies and risks across the business, and turn strategy into actions with owners and dates. You decide the sequencing and definition of done.

2. Operational infrastructure for the next stage of growth. You're the operational lead across Legal Ops, AI Ops, People Ops, Exec Ops and Finance. You own the initiatives that get these functions ready to scale, and you decide what ships first.

3. Cross-functional coordination. You keep departments such as Sales, Product, Finance, People and Customer Success pulling in the same direction, clear blockers and settle competing priorities before they stall the work.

4. AI in the CEO's office. You build the automations and agent workflows that give leadership more capacity. You set what they can touch and what gets reviewed before they go live, and you report the hours saved. AI drafts from the source systems. You structure the output, check it, and own the milestones.

5. CEO time. You track how the CEO's time splits between strategic and operational work, and move it towards strategic.

Across Legal Ops, AI Ops, People Ops, Exec Ops and Finance, you lead the plans and the team. Elsewhere, you shape the plans, and department leaders and the CEO own them, including headcount and spend.

🤝 Who you work with

• CEO. Your manager. You prepare their decisions, run their cadence and carry their priorities across the business.

• The executive team. Your closest working group. You rationalise priorities and conflicts between their plans so execution stays on track.

• Department leaders and managers. The people who own the work inside each initiative. You hold the dates, surface the blockers and route decisions to the right person.

• Your direct reports across Legal Ops, AI Ops, People Ops, Exec Ops and Finance. You lead these functions and own the initiatives that change how they run as Sitemate scales.

• Sitemate's other Chiefs of Staff. This includes the Chief of Staff to the CPO, who covers Applied AI.

⚡ What needs to happen

• Take over the CEO's priorities list and make it a live programme. Every item gets one owner, a date, and its dependencies and risks mapped.

• Map the operational infrastructure across Legal, AI, People, Exec Ops and Finance. Find what won't hold at the next stage of growth and turn each gap into an initiative with an owner and a date.

• Baseline CEO time. Measure strategic versus operational time today, then move it.

✅ What success looks like

By 90 days

• You've mapped how Legal Ops, AI Ops, People Ops, Exec Ops and Finance run today, and agreed the first operational initiatives with an owner and a date for each

• You have a baseline for how the CEO's time is split between strategic and operational work

• At least one operational workstream runs AI-native, with coding agents doing work the team used to do by hand, and hours saved reported

By 6 months

• Dependencies and risks on CEO priorities are flagged before the date they would block

• The first operational initiatives have shipped, and each function you lead is tracked against its SLAs and KPIs in the leadership cadence

• Board and leadership artefacts are AI-drafted from the source systems, and your review happens before anything ships

• The CEO's strategic time is up against the 90-day baseline

By 12 months

• Departments plan to the operating cadence, and it runs without you needing to be in every meeting

• Legal Ops, AI Ops, People Ops, Exec Ops and Finance run on infrastructure built for the next stage of growth, and hit their SLAs without you chasing them

• The CEO is no longer involved in the day-to-day running of Legal Ops, AI Ops, People Ops, Exec Ops or Finance

• You've helped define the success measures for the CEO's office

🔧 Day-to-day

• Run the CEO's weekly priorities review: what moved, what's blocked and what needs a decision

• Run 1:1s and progress reviews with your direct reports, and clear what's blocking them

• Track each function against its SLAs and KPIs, and raise what's slipping before it reaches the leadership review

• Prepare decision briefs and leadership communications for the CEO

• Chase follow-through on commitments made in leadership meetings

• Build and fix the agents and automations the CEO's office runs on

• Pull together All-hands, board and shareholder material from the source systems

• Keep the cadence runbooks current

🧬 How we build

Our Operating Principles are non-negotiable behavioural standards, written down and used in reviews. The ones this seat lives and enforces:

• Distill the Noise. Eight opinions come in, and one clear problem and one decision go to the CEO.

• Don't offload the thinking to the next person. Every brief arrives with context, a recommendation and a date.

• If more than one person is responsible, no one is responsible. Every priority gets exactly one owner, and you hold them to it.

• Build With, Not For. Leaders co-design the cadence they'll run to, so they plan to it and don't work around it.

• No Star Treatment. The standard for plans and updates entering the cadence is the same for every department.

• Build the Business Like We Build Product. The CEO's office is measured, reviewed and iterated like a product surface.

And the values you'll be held to most visibly:

• Everything Engineered. Cadences, runbooks and decisions are written down.

• Quality Certified. Board reports, shareholder updates and agent output are accurate to the detail, or they don't go out.

• Handle With Care. You spot communication risk early and adjust tone or delivery before anything lands.

✅ Who this role is for

• You find and frame the problem before anyone asks, then see it through on a date you set

• You get things done through influence, and you're comfortable holding senior people to a standard when they don't report to you

• You work AI-first: you run several agents at once, and when one gets something wrong, you fix the agent

• You check the numbers before they go in front of a board

• You raise uncomfortable truths early, including upward

• You write clearly and briefly

🚫 Who this role is not for

• You're looking for an executive assistant role centred on diary and inbox management

• You'd publish an AI-drafted report without reading it end to end

• You pass problems up to the CEO in the same messy state they reached you

• You need a fixed job spec before you're comfortable starting

🛠 Skills and tools

Must have

• A track record of owning cross-functional programmes end to end through influence

• Experience running or scaling operational functions such as Legal, People or Finance through a period of growth

• Experience leading and developing a team of managers or specialists

• Experience owning board, investor or company-wide reporting

• Strong written communication: briefs, decision papers, leadership updates

• Comfort with data: you can build the model, reconcile the numbers and explain what moved

• Hands-on experience building AI workflows or agents you use in your own work

Nice to have

• Prior Chief of Staff, operations or founder experience, ideally in a B2B SaaS scale-up

• Comfort leading a Finance function: you can read a P&L, run a forecast and hold the numbers to account

• Familiarity with construction, infrastructure or other built-world industries

Essential tools

• Claude, ChatGPT or comparable LLM tools

• Claude Code or comparable coding agents

• Google Workspace, especially Sheets and Slides

• Confluence and Jira

• Slack

Bonus tools

• Airtable

• Zapier or Make

• Salesforce

• Loom

📖 Read before you apply

These are public, and they are how we actually operate. Candidates who have read them tend to have better conversations with us.

• The Sitemate Manifesto

• On How Sitemate Ships Now, In The Era of AI

• Zero Click Forms and Conversational Data Capture, the thinking behind Storm

• Taking AI To The Front Line

• On Sitemate's Values, Culture and DNA

• For The Managers and Leaders Building Sitemate

• On How Sitemate Makes Decisions

• On Operating Like a Pro Sports Team, Not a Family

🌏 Life at Sitemate

• Full transparency: monthly all-hands share metrics, hiring plans and financial performance. Levels, career frameworks and pay ranges are visible to every employee

• Player-coach leadership at every level, including the executive team

• Global team across Australia, the UK, the US and Canada

• Equity, 20 days annual leave plus sick, carer's and compassionate leave, 16 weeks primary and 6 weeks secondary carer parental leave, EAP, L&D budget, home office setup, weekly catered lunches, work-from-anywhere weeks, flex days