Principal

Summary 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 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 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 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 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.