Chief of Staff

👋 Thanks for stopping by and learning more about this role at Sitemate! ✨🏗️

We’d love to hear from you 👩‍💻👩🏽‍💻🧑🏿‍💻👨🏻‍💻

• →

  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

• 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

• 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

• 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

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

• 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

• 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

• Airtable

• Zapier or Make

• Salesforce

• Loom

• Claude, ChatGPT or comparable LLM tools

• Claude Code or comparable coding agents

• Google Workspace, especially Sheets and Slides

• Confluence and Jira

• Slack

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

• 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

• People of Sitemate to hear from the team directly

PLEASE Note:

• We hire directly and don’t work with agencies