Guidewire Transformation Manager

Guidewire Transformation Manager

Location: Canada – Hybrid

Employment Type: Permanent or Contract

Sector: Property & Casualty (P&C) Insurance / Insurance Technology

Experience Level: Senior Management

About the Opportunity

We are looking for an accomplished Guidewire Transformation Manager to play a pivotal role in delivering a major technology modernization initiative within the Canadian Property & Casualty insurance sector.

This position offers the opportunity to shape and lead business-critical transformation programs, modernizing legacy insurance platforms, introducing new digital capabilities, and improving how insurance products and services are delivered.

Working closely with executive leadership, business stakeholders, and technology teams, you will provide the strategic direction and hands-on delivery oversight required to achieve successful transformation outcomes.

The successful candidate will bring substantial Guidewire experience, strong commercial awareness, and an excellent understanding of the Canadian insurance landscape.

Your Key Responsibilities

Transformation Leadership

• Take ownership of large-scale Guidewire transformation programs, ensuring strategic objectives translate into achievable delivery plans.
• Develop and maintain implementation strategies, transformation roadmaps, program budgets, and delivery milestones.
• Guide organizations through core platform replacement, modernization, and Guidewire Cloud adoption.
• Oversee transformation initiatives spanning Guidewire PolicyCenter, ClaimCenter, and BillingCenter.
• Identify delivery challenges early, develop mitigation strategies, and ensure business priorities remain aligned with technology outcomes.

Program Execution & Delivery

• Coordinate multiple delivery streams, including solution design, configuration, integrations, data migration, testing, and deployment.
• Lead multidisciplinary teams involving business analysts, architects, developers, project managers, and external delivery partners.
• Establish effective governance structures, program controls, and performance reporting.
• Manage third-party consulting partners and systems integrators, ensuring accountability for agreed deliverables.
• Support Agile and hybrid delivery models, driving collaboration, efficiency, and continuous improvement.
• Oversee implementation readiness, cutover planning, business transition, and post-deployment stabilization.

Canadian Insurance Market Alignment

• Collaborate with insurance business units supporting Canadian personal and commercial lines, including automobile, property, casualty, liability, and specialty insurance products.
• Ensure technology transformation initiatives accommodate applicable provincial and federal regulatory requirements.
• Understand regional variations in insurance products, automobile insurance models, distribution channels, and underwriting practices.
• Partner with underwriting, claims, billing, actuarial, product, and broker distribution teams to improve business processes.
• Support appropriate regulatory and compliance considerations, including OSFI guidelines where applicable, provincial insurance requirements, and privacy obligations.
• Work with business stakeholders to ensure Guidewire capabilities support broker networks, policyholders, and evolving customer expectations.

Stakeholder Engagement & Business Change

• Build productive relationships with senior executives, business sponsors, technology leaders, and delivery teams.
• Provide clear visibility of program performance, financial status, risks, and critical decisions.
• Promote organizational readiness and support the transition to new operating models and technology platforms.
• Work with business leaders to improve processes, reduce operational complexity, and encourage adoption of new capabilities.
• Define and monitor measures of success, ensuring investments produce tangible operational and commercial benefits.

What We're Looking For

Essential Experience

• 10+ years of experience in technology delivery, business transformation, or enterprise program management.
• A minimum of 5 years leading Guidewire implementations, modernization programs, or complex Guidewire delivery initiatives.
• Demonstrable experience working with Canadian P&C insurance carriers and an understanding of the Canadian insurance ecosystem.
• Strong knowledge of Guidewire InsuranceSuite, particularly PolicyCenter, ClaimCenter, and BillingCenter.
• Experience managing enterprise-level, multimillion-dollar technology transformation initiatives.
• Knowledge of Canadian personal and commercial insurance operations, distribution channels, and regulatory requirements.
• Proven ability to coordinate large teams, external consulting organizations, and geographically distributed stakeholders.
• Strong understanding of program governance, financial planning, delivery risk, and organizational change.
• Experience with Agile, SAFe, or hybrid project delivery methodologies.
• Exceptional leadership, communication, stakeholder management, and decision-making capabilities.

Additional Skills That Would Be Advantageous

• Previous involvement in Guidewire Cloud migration or SaaS adoption programs.
• Guidewire certification or formal training in Guidewire implementation methodologies.
• Experience working with Canadian national insurers, regional carriers, or leading insurance consulting organizations.
• Knowledge of Canadian insurance technology platforms, enterprise integrations, and data modernization.
• PMP, PgMP, SAFe, or comparable professional certification.
• Familiarity with regulatory bodies such as FSRA in Ontario, AMF in Québec, and other applicable provincial regulators.
• Experience implementing new digital insurance capabilities, automation, and operational transformation initiatives.

What You'll Bring to the Role

We are particularly interested in individuals who can demonstrate a successful history of translating complex transformation strategies into practical business outcomes.

You will be comfortable operating at executive level while retaining the technical and operational understanding required to challenge delivery plans, resolve issues, and maintain momentum across major programs.

A collaborative leadership style, commercial judgment, and the ability to navigate the complexities of large Canadian insurance organizations will be essential.

What Success Will Look Like

• Guidewire transformation initiatives delivered against agreed scope, quality, financial, and schedule objectives.
• Successful migration from legacy systems to modern insurance technology platforms.
• Strong business adoption and smooth operational transitions.
• Improved efficiency across claims, underwriting, billing, and policy administration.
• Effective collaboration between internal stakeholders, external vendors, and delivery teams.
• Measurable improvements in customer experience, business agility, and operational performance.

Apply

If you are an experienced Guidewire transformation professional with a strong understanding of the Canadian P&C insurance market and a passion for delivering meaningful technology change, we would welcome the opportunity to speak with you.

• Join a transformational program helping shape the next generation of insurance technology in Canada.