Development Manager, Guidewire

Canadian Automobile Association (CAA)

• $110K — $130K *
Thornhill, ON L3T 0A1In-Person
Finance & Insurance
Less than 5 years of experience
Today
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Job Overview by Ladders

Qualifications

  • Bachelor's degree in Computer Science or a relevant discipline
  • 4+ years of leadership experience in management or team leadership roles
  • 8+ years of professional application development in enterprise systems
  • Strong understanding of SDLC and Agile methodologies
  • Hands-on experience in software development and testing
  • Deep knowledge of Guidewire Insurance Suite and related tools
  • Proficiency in Java, GOSU, JavaScript/TypeScript for enterprise development
  • Experience in evaluating system architectures and design recommendations

Responsibilities

  • Establish governance for application architecture and standardize reporting
  • Provide technical leadership and foster a collaborative culture
  • Lead a development team delivering insurance solutions
  • Oversee solution design and ensure code quality through reviews
  • Support AI adoption to enhance productivity in the SDLC
  • Collaborate with stakeholders to ensure clear requirements and on-time delivery
  • Monitor KPIs and improve delivery metrics based on insights

Benefits

  • Hybrid work model offering flexibility
  • Continuous learning opportunities for professional development
  • Collaborative and innovative company culture
  • Engagement in modern tools and automation
  • Focus on operational excellence and continuous improvement
Full Job Description
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


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* Ladders Estimates

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