Who We Are
iSelect and Compare the Market are trusted, well-known brands dedicated to helping millions of Australians compare and buy personal finance and household products such as insurance, energy, and loans. Together, we provide a seamless, customer-focused experience that makes it easier for Australians to find the right products to suit their needs.
What You’ll Be Doing
The Head of IT Delivery sits within Software Engineering and leads the Centre of Excellence for initiative delivery across the Aggregation business. Responsible for leading a high-performing team of Delivery Leads, the role ensures initiatives are delivered predictably, transparently, and aligned to business priorities through a consistent delivery framework.
The role oversees quarterly planning, governance forums, portfolio health, capacity and dependency management, and delivery reporting through metrics, dashboards, and stakeholder communication. It also drives continuous improvement, fosters an agile delivery culture, and champions the adoption of AI-enabled tools and ways of working to improve delivery outcomes, productivity, and decision-making.
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Recruit, lead, coach, and develop Delivery Leads embedded across Software Engineering teams.
- Champion and continuously improve the delivery model for Initiatives, ensuring intake, triage, governance gates, delivery cadence, and artifact standards are consistently applied.
- Design and facilitate quarterly planning, big room planning, and other initiative planning events to align business objectives, capacity, risks, and dependencies.
- Plan, chair, and lead SteerCos across 4-5 initiative streams, preparing decision-ready packs, managing risks, and tracking actions to completion.
- Oversee portfolio governance across Initiatives, including capacity management, WIP limits, prioritisation, and dependency management.
- Maintain effective communication with stakeholders and provide visibility of delivery health through metrics, reporting, and governance forums.
- Drive the adoption of AI-enabled ways of working across delivery teams, identifying opportunities to improve productivity, delivery outcomes, forecasting, reporting, and decision making through the effective use of AI tools and automation.
- Partner with Technology and Business leaders to evaluate emerging AI capabilities and embed them into delivery practices, ensuring teams are equipped to leverage AI safely, effectively, and responsibly.
What’s In It For You
At Compare the Market and iSelect, we’re all about helping people make smart choices – and joining us might just be yours. We offer an environment where your ideas are heard, your contributions are valued, and your growth genuinely matters. Collaboration is part of our DNA and you’ll be joining a supportive, forward-thinking team where you can do meaningful work (and be recognised for it!)
We’re guided by three shared values that shape how we work, how we treat each other, and how we show up for our customers - Drive, Noble Intent and All Together.
Plus, we offer a range of great perks to help you thrive both in and out of work:
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Vibrant and social community who have annual celebrations, family fun days and regular events
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Enjoy flexible work arrangements, including the option of one day working from home each week or a 9-day fortnight
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Enjoy additional leave days - ‘ME’ leave and ‘Volunteer Day’ leave
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Option to purchase additional leave
- Return To Work bonus for returning parents
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Quarterly Award and Recognition program
What Sets You Apart
- Technology-related degree or equivalent industry experience.
- 5+ years' experience in software delivery leadership roles (e.g., Head of Delivery, Delivery Manager, Delivery Lead, Agile Coach).
- Experience designing and facilitating quarterly planning, PI planning, and large-scale multi-team planning events.
- Proven track record of chairing SteerCos or governance forums across multiple delivery streams.
- Hands-on experience with agile delivery methodologies, release management, and leading multiple technical teams.
- Experience working with modern delivery toolchains (e.g., Jira, Confluence, Azure DevOps).
- Strong facilitation, communication, stakeholder management, and influencing skills.
- Ability to operate effectively within a fast-paced, evolving environment.
- Demonstrated ability to coach teams, lead through influence, and embed agile ways of working.
- Demonstrated understanding of AI technologies and their application within software delivery environments, including the ability to drive adoption, governance, and productivity improvements through AI-enabled tools and practices.
- Experience leading organisational change and capability uplift initiatives related to emerging technologies, automation, or AI adoption is highly regarded.
Interested? Let’s chat!
At Compare the Market and iSelect we’re proud to be an Equal Opportunity Employer and we embrace diversity.
This role is available to candidates with unlimited Australian working rights only. Sponsorship is not available.
iSelect and Compare the Market, brands of iCompare Group, are committed to protecting your privacy. All applications and personal information are kept confidential and securely stored in line with Australian privacy laws, used only for recruitment purposes, and not shared with third parties outside iCompare Group without your consent.
