Chief of Staff

We’ve grown fast. Now we need someone to turn internal chaos into clarity.

Contour has done something uncommon: scaled from zero to a national education company in under six years, fully bootstrapped, with no outside capital. Eight-figure revenue. No investors. No playbook. The product works. The mission resonates. The demand is real.

We’ll be candid: this is a hard gig. But the ingredients are all there. The team is hungry, the appetite for change is genuine, and what’s needed is someone who can partner with the founders to channel that energy into structure, rhythm, and follow-through.

We’re looking for a Chief of Staff who is equal parts strategic and hands-on. An operator, a systems-builder, and a force multiplier for the founders. The connective tissue between the CEO, COO, and the rest of the company.

You won’t run a department. You’ll run the machine that makes every department run better.

At Contour, we’re reshaping education, one student at a time. 

Since 2020, over 10,000+ students have trusted Contour to guide their academic journey, and we’ve grown to over 300+ team members. We’ve produced hundreds of 99+ ATARs, tutored the World-Record UCAT scorer, and placed more students into medical school than any school in Australia. 

Our growth is a testament to the simple philosophy: Put the student first, always. Everything we design, from our world-class tutor-training programs to our purpose-built campuses, exists to help students master content faster, perform with confidence, and even rekindle the joy of learning. 

Contour is a group of three brands united by one goal: to give every student the best chance to achieve their full potential:

• Contour Education: Reshaping how students master their high school subjects with small-group tutoring, structured resources, and 1-on-1 support across Maths, Science, and English.
• Contour Medprep: Reshaping medical preparation with a proven, step-by-step pathway through the UCAT, interviews, and admissions, led by a team of 100+ medical students. 
• Contour TestPrep: Reshaping test preparation, starting with the selective entry exam, through rigorous tutoring, mock exams, and data-driven feedback to give students a decisive advantage. 

This is Contour. Built by students, for students.

Reporting directly to the CEO (co-founder) and working in close collaboration with the COO (the other co-founder). No initial direct reports, though this may evolve as the role develops.

Operating system and rhythm

• Own the operating cadence. Design and support weekly leadership meetings, monthly reviews, quarterly planning cycles, and annual townhalls. The right conversations, at the right frequency, with the right preparation.
• Own the full OKR lifecycle. Quarterly setting, progress tracking, mid-cycle reviews. Make sure annual objectives cascade into quarterly deliverables that people use.
• Cross-functional follow-through. When something touches Sales, Academics, Marketing, and Ops simultaneously, make sure there’s clear ownership, timelines, and accountability. You’re the one who catches what falls between departments.

Founder enablement and CEO initiatives

• Carry CEO-initiated projects to completion. The CEO can no longer take every strategic initiative from idea to execution. You scope them, build the plan, get the right people involved, and drive them to the finish line.
• Maximise founder leverage. Briefing packs, pre-reads, decision papers, meeting actions, follow-through. Make sure the founders’ time is spent on the highest-leverage work, not chasing updates.
• Make the leadership team sharper as a unit. Better meetings, clearer decisions, faster follow-through. You own the operating standard of the senior team.

Communications, culture, and strategic project

• Own internal comms. Every team member should know what’s happening, understand the why behind decisions, and feel prepared for what’s coming next. When leadership makes a call, the whole organisation hears about it clearly and quickly.
• Close feedback loops. Build structured channels between the team and leadership, and between students, parents, and leadership. People should see that their input leads to real change.
• Lead strategic projects without a departmental home. Campus launches, org restructures, system implementations, new market entries. You bring rigour and clarity to ambiguous problems.
• Use AI and automation to cut inefficient processes. We’re serious about this. You’ll identify the highest-value opportunities and drive adoption across the organisation, not just experiment.

You’ve held a Chief of Staff (or similar) role in a high-growth scale-up environment and you know what it takes (and feels like). More specifically:

• You’ve built the operating system, not just run it. You’ve designed or significantly improved the operating cadence of a scaling organisation and can point to what it actually changed.
• You’ve done OKRs for real. Not just facilitated a workshop. You’ve run the full lifecycle (setting, tracking, reviewing) and you’ve dealt with the messy reality of getting a leadership team to actually use the system.
• You can write. You’ve owned internal comms programs and you understand that alignment at scale is a communications problem as much as a strategy one.
• You’ve earned founder trust. You know how to manage up, manage across, and translate intent into action without needing to be told twice. You’re comfortable telling a founder their idea needs work.
• You’re fluent on the tools. Slack, HubSpot, Claude, whatever the stack is. You pick things up fast, and when something can be automated or hacked together to save time, you do it without waiting for IT.
• You can operate in a part-time-heavy workforce. Contour runs on ~400 people, roughly 80% of whom are front-line team (tutors, campus reps, and others). The operating rhythms, comms strategies, and feedback loops have to work for a team that isn’t in the office five days a week.
• You’re direct. Factual, clear, comfortable being blunt. You manage up without hesitation and handle stakeholder dynamics like a pro. No passive-aggressive Slack messages, just straight talk.

Bonus: Experience in education, multi-site operations, or organisations that have crossed the $100M+ revenue threshold.

Most Chief of Staff roles sit inside large corporates where the systems are already built, or inside early-stage startups where the scope is too broad and the infrastructure isn’t ready. This is the sweet spot: a bootstrapped, profitable company at the inflection point between startup and national brand, and your mandate is to build the operating infrastructure that carries it there.

• Build the engine. What you build will define how Contour operates for the next few years.
• Seat at the table. Direct access to both founders and every senior leader. No bureaucracy between you and the decisions that matter.
• Room to grow. This role starts as Chief of Staff. Where it goes depends on what you build and where your strengths take you.
• Competitive package. $180,000 – $220,000 + super, flexible hybrid working, EAP, birthday and loyalty leave, and lifestyle allowances.
• A mission worth your time. Every system you build flows downstream to students getting into the courses and careers they dreamed about.

If you’ve read this far and something in you is thinking “this is exactly what I want to do,” we want to hear from you.

Apply now or reach out directly to Angad at [email protected] with a short note on why this role is right for you.

We’re not looking for someone who ticks every box. We’re looking for someone who genuinely gets excited reading this and wants to help take a founder-led education company and give it the backbone to become something significant.

Ready to make a real impact? Here is our application process:

1. Submit your application.
2. Shortlisted candidates will complete a video interview and a case study-based assessment.
3. Suitable candidates will then be invited for a panel interview.