Job Description

Head of Delivery

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Enterprise SaaS | Sydney CBD

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Lead the delivery function that defines how enterprise technology gets delivered.

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This is not a "keep the lights on" delivery leadership role.

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This is an opportunity to take ownership of a growing delivery practice within a fast-scaling insurance technology business — shaping the standards, commercial performance, customer outcomes, and leadership capability that will define the next stage of growth.

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We're looking for a commercially minded delivery leader who knows how to operate at both strategic and operational levels.

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Someone who has led complex enterprise software implementations, understands the realities of consulting/vendor delivery environments, and knows how to build scalable delivery capability without losing customer trust along the way.

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You'll oversee all regional customer implementations while also defining the methodologies, governance, resource planning, delivery standards, and commercial discipline behind successful delivery outcomes.

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This role will suit someone who thrives in environments where:

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- delivery complexity is increasing
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- customers expect strategic partnership, not just project management
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- teams need structure, clarity, and accountability
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- commercial outcomes matter just as much as delivery quality
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What You'll Own

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Delivery Leadership

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- Lead all customer platform implementations across the region
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- Provide both hands-on oversight and leadership across the delivery function
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- Drive successful delivery outcomes across multiple enterprise customers and programs
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Delivery Practice & Capability

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- Define and continuously improve delivery methodologies, governance, tools, reporting, and operational standards
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- Build scalable delivery frameworks across both Agile and Waterfall environments
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- Uplift delivery capability, resource planning, and skills maturity across the team
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- Embed strong risk, issue, and change management practices
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Customer & Commercial Ownership

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- Build trusted relationships with senior customer stakeholders
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- Navigate complex delivery environments with confidence and credibility
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- Balance customer outcomes with commercial accountability and delivery profitability
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- Escalate and manage delivery risks proactively before they become customer issues
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Leadership & Influence

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- Partner closely with executive leadership on delivery strategy, resourcing, and operational priorities
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- Create clarity in ambiguous environments
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- Lead through influence, accountability, and collaboration
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About You

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You're likely coming from a:

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- software vendor
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- SaaS platform
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- consulting
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- professional services
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- insurance technology environment
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And you've spent years leading large-scale enterprise technology delivery where customer management, commercial outcomes, and delivery execution all sit under your remit.

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You'll bring:

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- Experience leading complex software delivery programs across multiple customers/accounts
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- Strong experience across both Agile and Waterfall delivery models
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- A track record of improving delivery practices, governance, and operational maturity
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- Strong commercial acumen and the ability to make commercially sound delivery decisions
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- Experience operating within insurance or financial services technology environments
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- Exceptional stakeholder management and communication skills
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- Confidence managing ambiguity, competing priorities, and executive-level conversations
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- A leadership style that combines accountability, collaboration, and high standards
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Why This Role?

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Shape the Function: This is a genuine opportunity to define how delivery operates — not simply inherit existing processes.

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Strategic Leadership Impact: You'll sit close to executive leadership and influence operational, commercial, and customer outcomes at scale.

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Complex, Enterprise Delivery: Work on large-scale insurance technology implementations with sophisticated customers and meaningful delivery challenges.

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Growth Setting: Join a business continuing to scale where delivery excellence is central to long-term success.

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📌 Head of Delivery | Enterprise SaaS Growth Leader (New South Wales)
🏢 Bespoke Careers
📍 New South Wales