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 c
onsulting/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
Solid 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.
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📌 Head Of Delivery | Enterprise Saas Growth Leader (Sydney)
🏢 Bespoke Careers
📍 Sydney