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Added 1 hour ago
NA
Client Manager, Personal Insurance
NFP, an Aon company (Canada)
Vaughan, ON
- Full-time
Excellent computer skills expected including fluency in Broker management systems – EPIC & ARS fluency are an asset
Added 4 hours ago
RB
Manager, Business Management & Optimization
Royal Bank of Canada
Toronto, ON
- Full-time
RBC Investor Services delivers critical services to the Investment Management and Broker/Dealer industries, including Trusteeship, Recordkeeping, Fund Accounting, and operational support…
Added 5 hours ago
NF
Senior Underwriter: Healthcare, Education and Social Services & Senior Care
Northbridge Financial
Toronto, ON
- Full-time
- Other
…Senior Care team (HESS). They work closely with a wide range of broker partners to get a holistic picture of each risk and make underwriting decisions that make sense for all parties. They…
Added 6 hours ago
F
Technical and Regulatory Specialist
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- Full-time
Disposal Broker Pricing: Maintain waste disposal pricing including sourcing and updating rates as required by the branches. Identify materials that lack pricing and source both outlets, as…
Added 7 hours ago
N
Manager, Security GRC
nesto
Canada
- Full-time
…share across direct-to-consumer (D2C) residential lending, the broker channel, and multi-family commercial lending. Recognized as one of Deloitte's Fast 50 companies for three consecutive…
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Manager, Processing - London, ON
Premier Canada Assurance
London, ON
- Full-time
Work closely with Underwriters to align processing support with underwriting priorities and broker needs.
Added 7 hours ago
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Insurance Advisor, Online Auto Services
Westland Insurance Group Ltd.
Surrey, BC
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Added 7 hours ago
SI
Manager, Underwriting Member & Co-operative Business
Sovereign Insurance
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Strong business acumen with knowledge of portfolio management, underwriting governance, risk controls, compliance requirements, and broker relationship management.
Added 7 hours ago
AC
Jr Underwriter Auto CI, IRCA
Aviva Canada
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- Full-time
Develop and maintain excellent broker relationships and management of assigned broker portfolio
Added 7 hours ago
AC
Senior Actuarial Analyst, Large Accounts Pricing
Aviva Canada
Markham, ON
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Added 8 hours ago
EI
Product Specialist (QC) - 12 month contract
Echelon Insurance
Quebec, QC
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Added 8 hours ago
TR
Spécialiste en fiabilité / Reliability Specialist
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Montreal, QC
- Full-time
Added 8 hours ago
QP
Leasing Coordinator - 14 Month Contract
QuadReal Property Group
Mississauga, ON
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Submit broker commission payments to accounting and process invoices in Yardi, including wire transfer coordination
Added 8 hours ago
HA
Sr Trade Compliance Analyst
Honeywell Aerospace
Mississauga, ON
- Full-time
Identify and resolve compliance issues, notices, penalties, CBSA inquiries, broker-service issues, and process gaps.
Added 8 hours ago
NF
Account Executive Underwriter
Northbridge Financial Corporation
Toronto, ON
- Full-time
We’re Northbridge Insurance. We’re proud to work with Canada’s most trusted commercial broker networks. We have a reputation for being one of Canada’s leading commercial insurance…
Added 9 hours ago
QP
Leasing Coordinator - 14 Month Contract
QuadReal Property Group
Mississauga, ON
- Full-time
Submit broker commission payments to accounting and process invoices in Yardi, including wire transfer coordination
Added 9 hours ago
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Insurance Broker
Western Financial Group
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Insurance Broker
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Added 9 hours ago
A
Senior Systems Engineer
Aviso
Vancouver, BC
- $100,000 to $120,000 CAD / year
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Added 9 hours ago
AW
Senior Systems Engineer
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Remote, Canada
- $100,000 to $120,000 CAD / year
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Added 9 hours ago
Intermediate Personal Lines Underwriter
Gore Mutual Insurance
Cambridge, ON
In this role, you’ll provide timely and effective underwriting support to our broker partners by managing inbound inquiries and processing referred risks. You’ll assess risks within your…
Added 9 hours ago
A
New Accounts Administrator
Aviso
Vancouver, BC
- $46,000 to $55,000 CAD / year
- Full-time
Added 9 hours ago
FC
Commercial Underwriter II
First Canadian Financial Group
Sherwood Park, AB
- Full-time
Client & Broker Interaction: Build and maintain strong relationships with both brokers and clients by providing responsive service, clear underwriting rationale, and communication.…
Added 9 hours ago
GM
Intermediate Personal Lines Underwriter
Gore Mutual Insurance
Cambridge, ON
- Full-time
In this role, you’ll provide timely and effective underwriting support to our broker partners by managing inbound inquiries and processing referred risks. You’ll assess risks within your…
Added 9 hours ago
NF
Category Specialist - Contract
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Us3 Consulting

Guidewire Transformation Manager

Toronto, ON, Canada

$160,000 to $195,000 CAD / year · Full-time

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Job details

Pay: $160,000 to $195,000 CAD / year
Job type: Full-time
Apply by: Dec 2, 2026
Experience: 10+ years of experience in technology delivery, business transformation, or enterprise program management.
Posting language: English
Posted: Nov 2, 2026

Original job description

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.

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More about this job

Responsibilities

Lead large-scale Guidewire transformation programs, including platform modernization, cloud adoption, implementation planning, and delivery across PolicyCenter, ClaimCenter, and BillingCenter. Coordinate multidisciplinary teams and vendors, manage governance and risks, and align technology changes with Canadian insurance operations, regulatory requirements, and business outcomes.

Requirements

Requires 10+ years of technology delivery, business transformation, or enterprise program management experience, including at least five years leading Guidewire initiatives and experience with Canadian P&C insurers. Candidates should have strong InsuranceSuite knowledge, multimillion-dollar program leadership, Canadian insurance and regulatory understanding, and expertise in governance, financial planning, change management, and Agile, SAFe, or hybrid delivery.

Skills

Guidewire Transformation
Program Management
Guidewire InsuranceSuite
PolicyCenter
ClaimCenter
BillingCenter
Canadian P&C Insurance
Program Governance
Financial Planning
Risk Management
Agile Delivery
SAFe
Stakeholder Management
Organizational Change Management
Data Migration
Guidewire Cloud Adoption

Visa sponsorship

Not detected in the job text

Keywords

Guidewire
Guidewire InsuranceSuite
PolicyCenter
ClaimCenter
BillingCenter
Guidewire Cloud
P&C Insurance
Canadian Insurance
Technology Transformation
Program Management
Program Governance
Program Budgets
Systems Integration
Data Migration
Solution Design
Testing
Deployment
Cutover Planning
Agile
SAFe
Hybrid Delivery
Organizational Change Management
OSFI
FSRA
AMF
PMP
PgMP
Insurance Regulation
Digital Insurance
SaaS Adoption

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