Technical Lead, Guidewire

CAA Club Group•Markham, ON

13d•Hybrid

About The Position

At CAA Club Group (CCG), we are passionate about keeping our Members safe and providing them with peace of mind through essential products and services. As a trusted Member-based organization with over 2.6 million Members across Ontario and Manitoba, we advocate for various issues and foster a collaborative work environment. CAA SCO Systems & Services Inc. is part of the CAA Club Group of Companies. We are an award-winning, purpose-driven organization committed to delivering an exceptional Associate experience with work-life harmony, continuous learning, incredible rewards, and competitive benefits.

Requirements

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

Responsibilities

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