Development Manager, 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

• Establish governance and standards for application architecture, development and set reporting frequency to keep leadership updated
• Provide technical leadership, remove delivery obstacles, foster a collaborative and innovative culture
• Lead development team of employees and contractors delivering insurance solutions
• Apply Guidewire best practices and secure development standards across the SDLC
• Oversee solution design and code quality including architecture reviews and structured peer code reviews
• Remain hands‑on when needed with coding, design discussions and troubleshooting
• Guide initiatives from concept to release ensuring alignment with business and technical objectives
• Support AI adoption within SDLC to enhance productivity and automation
• Collaborate with PMs, BAs, and Business stakeholders to ensure clear requirements and predictable delivery
• Ensure Agile commitments are met for scope, timelines and quality
• Proactively manage risks, issues and communicate impacts to stakeholders
• Monitor KPIs and delivery metrics and recommend improvements
• Define and evolve technical direction for application platforms and roadmaps
• Evaluate vendor and partner solutions for scalability and integration with Guidewire and enterprise systems
• Drive adoption of modern tools and automation to improve efficiency and quality
• Ensure software quality, reliability and scalability across all deliverables
• Support operational readiness including monitoring, performance validation and production alignment
• Champion operational excellence through continuous improvement in quality, productivity, and processes
• Partner with systems integrators, vendors, and internal stakeholders
• Develop and manage Statements of Work (SOWs)

Who You Are

• Bachelor’s degree in Computer Science or a relevant discipline
• 4+ years of leadership experience with prior roles as manager or team leader
• 8+ years of professional application development experience across enterprise systems
• Strong understanding of SDLC, development best practices, peer review processes and modern Agile methodologies
• Hands-on background in software development and testing with the ability to guide technical team
• Experience with Guidewire Insurance Suite and related development tools, frameworks and integrations
• Solid knowledge of P&C insurance domain, products, processes and system integrations
• Proficiency in Java, GOSU, and JavaScript/TypeScript for enterprise application development
• Experience evaluating system and application architectures and making design recommendations
• Proven ability to hire, mentor and develop talent while building engaged and high-performing team
• Strong adaptability and flexibility in managing shifting priorities and complex delivery environments
• Ability to manage conflict and build consensus using logical and data-driven communication
• Experience with cloud-hosted enterprise applications, SaaS platforms and modern DevOps tools (source control, issue tracking, build/release)
• Experience using AI coding assistants (e.g., GitHub Copilot, OpenAI Codex, Claude) to enhance development productivity and code quality
• Guidewire ACE Certified
• Experience with digital modernization initiatives

Preferred Skills

• Experience with Guidewire Cloud Platform or Guidewire upgrade initiatives
• Hands-on experience with cloud deployments on AWS or Azure
• Familiarity with microservices architecture, cloud-native development patterns and modern software development practices

Our Commitment