Director, AI Strategy & Transformation (2 year contract)
Oneflare
Software Engineering, Data Science
Sydney, NSW, Australia · Remote
Location
Sydney (Hybrid)
Employment Type
Contract
Department
Engineering
Hey there! Thanks for stopping by. We’re Airtasker, the tech company that connects people who need to get things done with those who have the skills to do it.
Our mission is to empower people to realise the full value of their skills. This doesn’t just apply to those who use our product. It’s also for our whole team of go-getters who bring the product to life and deliver impact to our community on a daily basis. Because we believe work (and life) is always better when you truly know and appreciate your strengths and skills.
This is a rare opportunity to shape how AI transforms an organisation - not by inheriting an existing program, but by defining it from scratch. As Director of AI Strategy & Transformation, you will own Airtasker's enterprise-wide AI agenda: setting the vision, building the operating model, prioritising what we pursue first, and leading the business through the change required to make AI genuinely stick.
You'll work closely with the CEO, CTO, and Executive Leadership Team to align AI investment to business priorities - and you'll be accountable for the outcomes, not just the strategy. This is a hands-on, high-ownership role for someone who wants to leave a lasting mark on how a marketplace business uses AI to grow.
What you'll do:
Strategy & Vision
Define and own the enterprise AI vision, strategy, and multi-year roadmap
Identify and prioritise high-value AI use cases across functions - balancing impact, feasibility, and speed
Establish the AI operating model: governance, frameworks, tooling, and ways of working
Monitor AI trends and emerging technologies to keep Airtasker ahead of the curve
Delivery & Execution
Lead end-to-end delivery of AI initiatives - from ideation through to implementation and optimisation
Define and track success metrics: ROI, productivity gains, and cost efficiencies
Build and scale a high-performing AI transformation function
Stakeholder & Executive Engagement
Partner with the CEO, CTO, and ELT to align priorities and secure investment
Build credibility and trust with both executive and technical audiences
Work cross-functionally across Product, Engineering, Data, People, Finance, and Operations
Adoption & Change
Embed AI solutions into day-to-day workflows - not just deploy them
Lead organisation-wide change management, capability uplift, and behavioural transformation
Drive genuine adoption by bringing people on the journey, not just communicating at them
We'd love to hear from you if you tick some of these boxes:
You'll bring experience in
Defining or significantly contributing to an enterprise AI or transformation strategy
Influencing and securing buy-in at CEO and executive level
Leading large-scale programs end-to-end - not just contributing to them
Driving adoption and behaviour change, not just delivering change
Prioritising initiatives based on commercial value, not technical interest alone
Operating in ambiguous, fast-paced environments where the playbook doesn't exist yet
You'll demonstrate
Genuine, hands-on engagement with AI - personal use and formed opinions, including where AI falls short
The ability to translate complex concepts into clear, commercially grounded language
Strong ownership - you build things, you don't just advise on them
Intellectual honesty and self-awareness about your gaps
Curiosity about AI that shows up in how you work, not just what you say
Collaborative instincts - you influence without authority as naturally as you lead with it
Our People Experience:
Our people team at Airtasker are dedicated to designing an industry leading people experience. This means creating an environment where you are empowered to do your best work and realise the full potential of your skills.
Thriving
Hybrid working - when it comes to working, there’s no “one size fits all” approach, with Airtasker you choose the environment that helps you do your best work.
Airtime - welcome to no Slack and meeting-free Fridays! Airtime is designed so we regularly have dedicated focus time for work and personal growth.
Recharge days - each quarter we have a company-wide Recharge Day, equivalent to 4 additional days of leave per year. It’s a day for everyone when the world can wait and self-care takes centre stage.
Wellbeing support - our Employee Assistance Program provides confidential access for our people to GPs, dieticians, counselling and mental health specialists, providing essential support whenever needed.
Airpowerment Fund - we provide a $200 allowance to spend on anything that supports your health & wellbeing.
Rewarding
Airtasker credits - it’s a great feeling to get things done. Even greater when you get $1000 worth of credits every year to help you check off your to-do list and connect with our community of Taskers.
Fair and equitable pay - this is a core commitment to our people. Every year we review industry data to ensure our compensation framework supports everyone to be recognised for the full value of their skills.
Tenure leave - To celebrate our people’s commitment to Airtasker, we offer tenure leave starting from your 3rd anniversary with the company. This begins with 3 extra days of leave per year, gradually increasing to a maximum of 5 days per year.
Belonging
DAREtasker - join our Diversity, Equity and Inclusion committee! Every month we meet to create meaningful and impactful programs of work that embrace belonging at Airtasker.
Celebration swap - not everyone celebrates the same things. That’s why, at Airtasker, you can swap national, state or territory public holidays for the ones that matter to you.
Growing
Learning and development - learning at Airtasker is on the job, guided by managers, enhanced by peers and led by ourselves. We deliver learning programs and budget allowances to invest in your growth.
360 performance reviews - feedback is a gift. Every year we run 360 reviews across the business to recognise achievements and promote personal growth.
Volunteer leave - Our team members can take a day each year to lend a helping hand and support a cause they are passionate about.
Celebrating
Awards - and the winners are… our go-getters! Whether it’s our peer-nominated quarterly Values Awards or our periodic Go-Getter Spirit Award, we love celebrating our people and spreading good energy.
Vibe committee - good vibes only! Our Vibe Committee delivers events that hit the sweet spot of bringing us all together to enjoy each other’s company whether you’re local or remote.
Birthday leave - All of our people get an extra day of leave during their birthday week to take time away from work to celebrate.
At Airtasker we believe in culture add - that each person is different and has their own background, learnings and unique experiences that can add to the Airtasker cultural tapestry. We pride ourselves on our inclusive culture, and encourage applications from people of all backgrounds.
To all recruitment agencies and talent suppliers: Airtasker does not accept unsolicited resumes. Airtasker is not responsible for any fees related to unsolicited resumes. Please do not forward resumes to our job postings or directly to our managers. If you are on our supplier list and have terms in place, ensure you work alongside our internal TA team and do not send resumes directly to managers.
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