Head of Delivery

Enterprise SaaS | Sydney CBD

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

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

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.

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

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.

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

This role will suit someone who thrives in environments where:

• delivery complexity is increasing
• customers expect strategic partnership, not just project management
• teams need structure, clarity, and accountability
• commercial outcomes matter just as much as delivery quality

What You’ll Own

Delivery Leadership

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

Delivery Practice & Capability

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

Customer & Commercial Ownership

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

Leadership & Influence

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

About You

You’re likely coming from a:

• software vendor
• SaaS platform
• consulting
• professional services
• insurance technology environment

And you’ve spent years leading large-scale enterprise technology delivery where customer management, commercial outcomes, and delivery execution all sit under your remit.

You’ll bring:

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

Why This Role?

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

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

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

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