Principal
Australia - Sydney
Professional Services/Full time/Hybrid
The Role
The Principal is the Services leader/owner of the Customer Account and the field leader on all implementation-related topics.
You'll be responsible for the success of the cloud transformation programs, ensuring that projects stay on track and that Guidewire delivers real value to the customer's business. You will lead implementation planning with customers from pre-sales through to delivery, owning the end-to-end estimation process in collaboration with internal functions and SI partners. You will be adept at structuring and managing both outcome-based and Fixed Price engagements, ensuring commercial constructs are aligned to delivery realities and customer expectations.
You will bring firsthand experience delivering programs through a Global Delivery Model, coordinating onshore, nearshore, and offshore teams across time zones while maintaining delivery quality, governance standards, and customer confidence. You will understand the operational disciplines required to make distributed delivery work effectively — from knowledge transfer and team integration to communication cadences and escalation protocols.
You'll coordinate internal and external teams, manage delivery risks, and serve as a trusted advisor to customer stakeholders across the Australia-Japan market. A deep understanding of P&C insurance operations, regulatory environments, and market dynamics in this region is essential to this role. You'll also work closely with Sales, Product, and other internal teams to ensure smooth delivery, clear communication, and long-term success.
Your background will reflect experience gained within a Global System Integrator or a SaaS-based product company, giving you a strong foundation in structured delivery methodologies, commercial engagement models, and the operational realities of delivering enterprise software at scale. This background will inform how you engage with SI partners, shape customer proposals, and lead delivery governance across complex programs.
You will advocate for customers' needs with partners and internal teams while being accountable for the portfolio's financial performance and revenue growth.
Job Description
Key Responsibilities
Cloud Program Leadership
Lead the planning and execution of cloud transformation programs across assigned customer accounts in the Australia/Japan market
Own end-to-end implementation planning with customers, establishing delivery roadmaps, resource models, and milestone frameworks from engagement inception
Design and govern Global Delivery Model structures for assigned programs, defining the split of responsibilities across onshore, nearshore, and offshore teams and ensuring effective integration across all delivery locations
Establish the governance, communication, and escalation frameworks required to manage distributed delivery teams effectively, including time zone coordination, knowledge transfer protocols, and quality assurance across locations
Coordinate key activities like performance testing, cutovers, and handovers to customer success
Monitor progress, identify risks, and work with delivery teams to keep programs on track
Ensure customer programs align with business objectives and success criteria
Structure and govern Fixed Price engagements, managing scope boundaries, change control processes, and margin protection throughout the delivery lifecycle
Lead outcome-based engagement models, defining measurable success criteria, aligning delivery milestones to business outcomes, and proactively managing customer expectations
Customer Relationship and Advocacy
Act as a trusted delivery partner to customer stakeholders and SI partners across Australia or Japan
Provide strategic input on how customers can best leverage Guidewire products and services within the context of local P&C insurance market requirements, including regulatory frameworks such as APRA or FSA, and regional product lines
Apply strong insurance domain knowledge to guide customers on industry best practices, line of business considerations, and operational transformation specific to the Australia-Japan market
Draw on GSI or SaaS product company experience to bring structured, scalable thinking to customer engagement design and delivery governance
Advocate for customer needs within Guidewire — collaborating with Product, Cloud Ops, and Support
Support governance activities like steering committees and executive reviews
Sales and Pre-Sales Support
Support sales teams by contributing to cloud transformation proposals and services estimates, including Fixed Price and outcome-based commercial constructs
Lead the development of implementation estimates in close collaboration with Delivery, Cloud Ops, Product, and SI partners — ensuring estimates reflect realistic scope, complexity, and risk, including the cost and coordination overhead associated with Global Delivery Model structures
Participate in early conversations with customers to shape engagement plans, applying regional market insight to tailor solutions for the Australia-Japan context
Own small to mid-size opportunity proposals and help develop Statements of Work, including scope definitions appropriate for Fixed Price structures and Global Delivery Model resourcing
Identify expansion opportunities within existing accounts by leveraging delivery performance and customer relationships
Program Financial Management
Track budgets and forecast delivery costs across Fixed Price and time-and-materials engagements, including the financial implications of Global Delivery Model resourcing across multiple locations
Manage commercial risk in Fixed Price contracts through rigorous scope management, proactive change control, and margin monitoring
Contribute to overall account profitability by managing margin, staffing, and scope alignment across onshore and offshore resource pools
Ensure a smooth transition from implementation to BAU support and customer success
KPIs & Success Metrics
Program Success Rate — percentage of cloud implementations delivered on time, on scope, and within budget, with specific accountability for Fixed Price contract performance
Customer Engagement Quality — CSAT scores and stakeholder feedback from assigned accounts across Australia and Japan
Delivery Efficiency — accuracy of delivery forecasting, implementation estimates, staffing plans, and margin impact, including Global Delivery Model cost optimisation
Estimate Quality — accuracy of pre-sales implementation estimates measured against actual delivery outcomes
Establishing and achieving account-specific Services Revenue, Profitability, and Sales targets
At Guidewire, we foster a culture of curiosity, innovation, and responsible use of AI—empowering our teams to continuously leverage emerging technologies and data-driven insights to enhance productivity and outcomes.
Key Skills & Experience
Experience in enterprise software delivery, consulting, or transformation, gained within a Global System Integrator or SaaS-based product company
Experience in a customer-facing delivery leadership role, with accountability for program outcomes and customer satisfaction
Hands-on experience delivering large-scale cloud or SaaS implementations using a Global Delivery Model, with direct responsibility for coordinating onshore, nearshore, and offshore teams
Demonstrated understanding of the operational disciplines required for effective distributed delivery — including team integration, knowledge transfer, quality assurance across locations, and time zone governance
Demonstrated experience in structuring and managing Fixed Price engagements, including scope definition, change control, and margin management
Experience delivering outcome-based engagements with clearly defined success metrics and milestone-linked delivery models
Proven ability to lead implementation planning and develop detailed delivery estimates in collaboration with internal teams and SI partners, incorporating Global Delivery Model resourcing and cost structures
Strong knowledge of the P&C insurance industry in Australia and/or Japan, including regulatory environments such as APRA or FSA, common lines of business, and operational workflows
Strong communication and relationship-building skills with customer stakeholders across diverse cultural and organisational contexts
Familiarity with budgeting, forecasting, and tracking financials at the program level across multi-location delivery models
Experience coordinating across delivery teams, SI partners, and customer teams in complex, matrixed environments
High-level understanding of cloud platforms and SaaS delivery models, informed by practical experience in a product company or GSI context
Ability to manage and mitigate delivery risks in complex, globally distributed environments
Proficiency with tools like Jira, Confluence, Power BI, or similar platforms
Strong sales acumen, capable of identifying and creating new sales opportunities through strategic thinking and proactive engagement
Demonstrated ability to embrace AI and apply it to your role as well as use data-driven insights to drive innovation, productivity, and continuous improvement.
Preferred Skills & Experience
15+ years of experience in delivering complex projects
Working knowledge of Guidewire Cloud Platform and associated services
Prior experience at a Tier 1 Global System Integrator, such as Accenture, Deloitte, Capgemini, Cognizant, or PWC, or within a SaaS-based enterprise software company in a delivery leadership capacity
Deep understanding of Australia and Japan P&C insurance market dynamics, product structures such as CTP, home, commercial lines, and non-life, and digital transformation trends
Familiarity with APRA prudential standards and Japan FSA regulatory requirements as they relate to core systems transformation
Experience working with Japanese insurers or Australian general insurers on technology modernisation programs
AWS or cloud platform certifications
PgMP, PMP, or SAFe certifications
Previous experience working with SI partners in the ANZ or Japan region, ideally from both sides of the relationship — as the GSI and as the product vendor
Familiarity with regulated industries such as insurance, healthcare, or banking
Prior experience in customer success, engagement management, or program delivery within a SaaS vendor environment
Exposure to commercials, including Fixed Price proposals, SOWs, and outcome-based pricing models within a GSI or product company commercial framework
Experience managing global or multi-region customer programs across Asia-Pacific, including programs with significant offshore delivery components
Comfortable working in fast-paced, matrixed environments with shifting priorities across multiple geographies and time zones
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Interested in this position?
About Guidewire
Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. We combine digital, core, analytics, and AI to deliver our platform as a cloud service. More than 540+ insurers in 40 countries, from new ventures to the largest and most complex in the world, run on Guidewire.
As a partner to our customers, we continually evolve to enable their success. We are proud of our unparalleled implementation track record with 1600+ successful projects, supported by the largest R&D team and partner ecosystem in the industry. Our Marketplace provides hundreds of applications that accelerate integration, localization, and innovation.
For more information, please visit www.guidewire.com and follow us on Twitter: @Guidewire_PandC.
Guidewire Software, Inc. is proud to be an equal opportunity and affirmative action employer. We are committed to an inclusive workplace, and believe that a diversity of perspectives, abilities, and cultures is a key to our success. Qualified applicants will receive consideration without regard to race, color, ancestry, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, gender expression, veteran status, or disability. All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.
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