Lead Java Developer (Remote/Hybrid or On-Site)

at  Insurance Insight Inc

Insurance Insight Inc. (formerly WALKAWAY® Canada Inc.) is headquartered in Oakville, Ontario, and is an insurance brokerage specializing in providing automotive manufacturers and dealerships in North America and around the world with high-quality insurance-based products and technology solutions. We specialize in large national automobile after-market products, such as creditors insurance and GAP insurance, enabling a minimum amount of administration with the maximum amount of return.
We are currently seeking a Lead Java Developer, someone who is passionate about leading our technology initiatives to new heights. This position can be in-office, hybrid, or fully remote. Our office and most of our team are based in the GTA, but we’re happy to hear from candidates based elsewhere in Canada.
We’re looking for talented people who share our passion for our mission to provide financial confidence to consumers for meaningful purchases. We’re a close-knit group that thrives on mutual respect and stays true to our core values of Purpose, Authenticity, Commitment, and Teamwork (PACT). Whether we are developing a new program, servicing an existing client, or settling a claim, we always aim to go beyond expectations. You’ll be part of a team that’s the best at what they do, and we’re proud to maintain a 4.8-star Google Review rating. Thanks to our dedicated team, our company is a great place to work and a great partner for our customers.
This is a hands-on leadership role, suited for a “Java Ninja” who has a deep passion for Java and its vast ecosystem. As the Lead Java Developer, you’ll report to our Solutions Owner. You’ll design, develop, and maintain high-quality Java applications, ensuring they meet both functional and non-functional requirements. As a key member of our solutions team, you’ll be involved in every stage of building advanced solutions, applying your technical expertise to make a real impact. Your insights are valued, and you understand the importance of effective teamwork. In our no-ego environment, flexibility is key, and responsibilities will range from building and maintaining robust enterprise systems, to leading and mentoring a team of software developers to owning the entire software development lifecycle, performing code reviews, and troubleshooting complex issues.
This role will enable you to leverage your existing technology skills while building new ones, shaping the company’s future together, and having some fun along the way.

QUALIFICATIONS & SKILLS

Technical:

• Senior-level hands-on programming experience in Java development (minimum 5 years), with deep expertise in Spring, Spring Boot, Spring Security, Spring Cloud, and Hibernate
• Strong proficiency in working with Maven
• Strong proficiency in working with PostgreSQL and other relational databases
• Proven experience in designing and managing CI/CD pipelines, particularly with GitHub Actions and GitLab Pipelines
• Familiarity with Google Cloud Platform (GCP) and Google Kubernetes Engine (GKE)
• Knowledge of security frameworks and hands-on experience with automated security tools
• Experience with HTML, JavaScript, and CSS for seamless front-end integration
• Experience with GWT (Google Web Toolkit) application development is an asset
• Experience with data warehousing, business intelligence tools, data analysis and visualization, and ETL processing is an asset

Leadership & Management:

• Proven experience in leading and mentoring a team of developers and DevOps professionals.
• Experience with Agile/Scrum methodologies and EOS is an asset.
• Ability to manage teams across multiple time zones.

You also bring:

• Strong communication and organization skills with attention to detail
• Focus and the ability to work both independently and collaboratively
• A passion for owning the solution from concept to deployment and beyond
• Experience with CloudFlare, Terraform, Docker, and Kubernetes is an asset
• Familiarity with UX/UI development and tools like Figma is beneficial
• Experience with legacy system migration and multi-tenant SaaS applications is a plus
• Industry experience in automotive, financial, insurance, transactional systems, or ERP systems is highly valued

Working Conditions:
The Lead Java Developer will work in a typical office environment whether remote or hybrid and have the ability to work across multiple time zones.
Benefits and Perks:
We provide a competitive compensation and benefits program, including health, dental, life insurance, disability, group retirement savings, and three week’s vacation to start. We will provide you with all the necessary tools you’ll need to be effective in your new role.
We are looking for people who share our values, first and foremost, to join our team. We believe our team members represent our single biggest investment and our most valuable asset. We know that in today’s highly competitive job market, talented people can work anywhere. Our values and culture are sacred; they define and differentiate us from other employers. We are proud to be named one of Canada’s Most Admired™ Corporate Cultures and a Top Insurance Workplace.
If you are driven by the need to make a difference, have a high regard for the customer and thrive on team success, please apply with your cover letter and resume to hr@insuranceinsight.ca.
Insurance Insight welcomes applications from people with disabilities. Accommodations are available on request for candidates participating in any aspect of the application, assessment and selection process.
Job Types: Full-time, Permanent
Pay: $100,000.00-$130,000.00 per year

Additional pay:

• Bonus pay

Benefits:

• Casual dress
• Company events
• Dental care
• Disability insurance
• Employee assistance program
• Extended health care
• Life insurance
• Paid time off
• RRSP match
• Tuition reimbursement

Technical Development:

• Write high quality and well-documented code according to accepted standards based on business requirements
• Lead the development and maintenance of Java-based applications, leveraging frameworks like Spring Boot, Spring Security, Spring Cloud, and Hibernate
• Participate in architectural discussions and contribute to the design of software systems, including prototyping and selecting appropriate technologies and frameworks
• Champion code quality by actively engaging in the development process and conducting thorough reviews
• Analyze and troubleshoot complex issues in applications and provide effective solutions
• Write unit tests and integration tests to ensure code reliability and maintainability
• Create and maintain technical documentation for code, processes, and systems to facilitate knowledge sharing and onboarding
• Oversee deployment processes through CI/CD pipelines, utilizing GitHub Actions and GitLab Pipelines to ensure smooth and efficient releases
• Manage application deployments to Google Cloud Platform (GCP) and Google Kubernetes Engine (GKE), focusing on scalability, performance, and reliability
• Stay updated on emerging technologies, industry trends, and best practices in Java development and software engineering

Leadership & Management:

• Lead, mentor, and coach a team of developers and DevOps professionals in order to meet deadlines
• Utilize modified Agile/Scrum methodologies to manage and deliver projects effectively
• Drive the implementation of the Entrepreneurial Operating System (EOS) within the team
• System Management & Security:
• Conduct security assessments and proactively remediate vulnerabilities and issues
• Address and resolve technical debt, ongoing security and patch management, and migration of older legacy applications
• Take ownership of system availability, ensuring continuous uptime and reliability
• Work with third-party vendors and automated tools to run penetration tests, perform static code analysis, and address security vulnerabilities
• Review, maintain, and test disaster recovery plans to ensure readiness
• Govern security policies and procedures for compliance and effectiveness

Communication & Collaboration:

• Work directly with the Solutions Owner to ensure that technology initiatives align with business goals
• Serve as the primary technical liaison with the technology team, ensuring clear communication and alignment of objectives
• Translate business requirements into scalable and reliable technology solutions