Technical Lead, Guidewire

About Us

At CAA Club Group, we are passionate about keeping our Members safe - whether they are on the road, at home, or travelling abroad. As a trusted Member-based organization, we provide products and services that are essential to Members’ safety and peace of mind. With over 2.6 million Members across Ontario and Manitoba, we advocate on issues such road safety and infrastructure, the environment, seniors’ mobility, and consumer protection. Associates share in each other’s successes, drive change and support each other while cultivating a great working environment to deliver on what is best for our Members. CAA SCO Systems & Services Inc. is a member of the CAA Club Group of Companies. 

Who we are

Are you ready to join an award-winning, purpose-driven culture? Welcome to the CAA Club Group of Companies (CCG), where purpose leads to passion!

• At CCG, we are committed to delivering an exceptional Associate experience. We offer:
• Work-life harmony with access to an award-winning holistic wellness program,
• Continuous learning through our robust corporate curriculum and education reimbursement program,
• Incredible rewards, travel incentives, and product and service discounts,
• Pay-for-performance and best-in-class recognition programs, and
• Competitive benefits that include a defined contribution plan, personal spending account, and so much more.

Join our growing team where everyone belongs!

Position Details

What You Will Do

• Lead Guidewire technical direction across PolicyCenter, BillingCenter, and ClaimCenter by defining scalable configuration, customization, and integration approaches
• Perform hands‑on development in GOSU, PCF, product model, rules, plugins, messaging, and integration frameworks for enhancements, defects, and production fixes
• Review and approve technical designs to ensure alignment with architecture standards, performance expectations, and maintainability requirements
• Enforce coding standards, conduct structured code reviews, and drive engineering discipline across the development team
• Serve as the final technical escalation point for complex Guidewire issues, production incidents, and cross‑system integration challenges
• Lead release development cycles by coordinating developer activities, assigning work, tracking progress, and ensuring delivery readiness
• Provide technical mentorship to developers, guiding solution design, debugging approaches, and best‑practice implementation patterns
• Validate requirements with BAs and business stakeholders, propose optimal technical solutions, and deliver accurate estimations and implementation plans
• Identify technical risks and dependencies early to ensure predictable delivery and proactive mitigation
• Plan and manage hotfixes and recurring releases including monthly and bi‑monthly Guidewire upgrade cycles
• Ensure regression coverage and release readiness by partnering with QA to validate test scope, quality gates, and defect resolution
• Collaborate with Application Support to troubleshoot production issues, perform root‑cause analysis, and ensure stable post‑release operations
• Work closely with PMs to track milestones, dependencies, and risks; with BAs to align delivery to business priorities; with QA Leads to ensure quality; and with Support Leads to maintain production stability
• Communicate clear technical status, risks, and recommendations to leadership and stakeholders with strong ownership and accountability

Please note, salary range is not inclusive of total compensation. The expected salary range for this position will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. Candidates with salary expectations outside of the range are encouraged to apply.

Who You Are

Required Qualifications

• 10+ years of overall software development experience
• 5+ years of hands‑on Guidewire PC/BC/CC experience
• Solid understanding of P&C insurance domain.
• Strong hands‑on experience with Guidewire Insurance Suite, GOSU, PCF, rules, product model, configuration, APD, integrations (web services, messaging, plugins) and Guidewire integration framework.
• Solid understanding of Guidewire data model, batch processes and performance tuning
• Experience in Guidewire's Cloud Data Access platform
• Experience with version control, CI/CD pipelines, and release management practices
• Strong debugging, troubleshooting and production‑support skills
• Strong experience managing frequent releases and production hot‑fixes
• Ability to balance hands‑on technical work with coordination responsibilities
• Experience working in Agile or hybrid delivery models
• Bachelor’s degree in Computer Science or a relevant discipline
• Prior experience as a Senior Developer or Technical Lead required
• Guidewire ACE Certified

Please note that internal applicants are asked to formally express their interest by applying online no later than 10 business days of the position being posted. 

Please note that we may use AI tools to help us through the recruitment process

Our Commitment

We are an equal opportunity employer and are committed to providing employment accommodation in accordance with all applicable Provincial Human Rights and Accessibility Legislation. CCG will provide accommodations to job applicants with disabilities throughout the recruitment process. If you require an accommodation, please notify us and we will work with you to meet your needs.

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