Lead Developer

Rival Insurance Technology; Toronto; Hybrid; CAD 100,000 - 140,000; Full time

Job summary

Rival Insurance Technology seeks a Lead Developer to modernize legacy software systems into scalable platforms. In this pivotal role, you will lead architectural design, mentor teams, and drive transformation in a collaborative, remote-friendly environment. Join us to create lasting technical and cultural impact in the insurance technology space.

Benefits

Remote-friendly workplace

Support for equity, inclusion, and accessibility

Opportunities for continuous learning

Qualifications

• 7+ years of progressive experience in software development, including legacy systems.
• Deep understanding of legacy Windows desktop technologies.
• Experience in modernizing applications using .NET Core and cloud approaches.

Responsibilities

• Lead architectural design and modernization of legacy software systems.
• Foster a culture of engineering excellence and continuous improvement.
• Lead strategic planning efforts for modernization projects.

Skills

Team Leadership

Architectural Design

Legacy System Modernization

Agile Methodologies

Communication

Education

Bachelor's degree in Computer Science

Tools

C#

.NET

SQL Server

PowerShell

React

Angular

Job description

As a Lead Developer at Rival Insurance Technology, you will play a pivotal role in transforming legacy software systems into modern, scalable, and maintainable platforms. You will lead architectural design, codebase assessments, and modernization strategies while fostering a culture of engineering excellence, learning, and continuous improvement. This role is ideal for a technically strong leader with deep legacy system experience, full-stack proficiency, and a passion for mentoring high-performing teams through change.

At Rival, we are reimagining the future of insurance technology. We’re looking for someone who brings expertise, empathy, and strategic thinking to modernize aging systems and uplift the developers behind them. If you're excited to drive transformation from the inside out, we want to hear from you.

Responsibilities

Legacy System Modernization

• Lead the assessment, planning, and execution of legacy software transitions (e.g., VB6, classic Windows desktop apps) to modern frameworks such as .NET (WinForms, WPF, MAUI) and microservices.
• Analyze codebases for scalability, maintainability, and performance, and define clear, phased modernization roadmaps.
• Provide hands-on technical leadership for migration paths, platform upgrades, and UI / front-end architecture.

Architecture and Technical Strategy

• Apply architectural patterns like Domain-Driven Design, layered architecture, and microservices to replace outdated structures.
• Introduce best practices, reusable patterns, and quality standards to modernize legacy codebases.
• Support the evolution of data systems—guiding transitions from legacy SQL databases to cloud-native and scalable alternatives.

Team Leadership and Transformation

• Evaluate team strengths; implement upskilling plans aligned with modernization goals.
• Foster a high-performance team culture through mentoring, pair programming, and regular code reviews.
• Establish and maintain modern coding standards across engineering teams.

Cross-Functional Communication

• Act as a trusted technical advisor—translating complex architectural goals into business-aligned priorities.
• Work with Product, Leadership, and other stakeholders to ensure clarity and momentum on modernization initiatives.
• Develop documentation, diagrams, and presentations to communicate technical vision and track progress.

Project Management and Delivery Excellence

• Lead strategic planning efforts for modernization workstreams, aligning architectural decisions with business priorities.
• Scope and lead modernization projects using Agile methodologies, ensuring delivery timelines and budget goals are met.
• Identify potential blockers early and escalate when needed to maintain delivery velocity.

Culture and Continuous Learning

• Champion a culture of experimentation, learning, and continuous improvement
• Promote a culture of learning, experimentation, and curiosity—introducing modern engineering practices while respecting historical context.
• Stay current with emerging technologies and guide the team through continuous evolution in tooling, cloud practices, and DevOps.

Qualifications

Education / Experience :

• Bachelor’s degree in Computer Science, Engineering, or a related field (or equivalent experience).
• 7+ years of progressive experience in software development, including significant work with legacy systems and technical team leadership.

Technical Expertise :

• Deep understanding of legacy Windows desktop technologies (e.g., VB6, WinForms), and strong proficiency in C#, .NET, SQL Server, and PowerShell.
• Experience modernizing applications and platforms using .NET Core, WPF, MAUI, or cloud-native approaches.
• Exposure to modern front-end frameworks (e.g., React, Angular) and cross-platform application strategies.

Architectural Mastery :

• Expertise in software architecture, design patterns, and modern paradigms including microservices and DDD.
• Experience in transforming monolithic applications to scalable, modular solutions.
• Track record of developing high-performing engineering teams and mentoring developers at all levels.
• Ability to foster team trust, collaboration, and shared ownership of outcomes.
• Strong interpersonal and communication skills to align technical work with business objectives.

DevOps & Development Practices :

• Familiarity with DevOps practices, CI / CD pipelines, cloud infrastructure (Azure preferred), and test automation.
• Experience working in Agile environments and managing change within complex, evolving codebases.

Why Join Rival Insurance Technology?

At Rival, you’ll be empowered to lead transformation that truly matters—reshaping outdated systems into modern, scalable platforms that power the future of insurance. You’ll join a collaborative, remote-friendly workplace that values authenticity, curiosity, and resilience. If you’re driven to create lasting technical and cultural impact, we’d love to hear from you.

We are committed to equity, inclusion, and accessibility. If you require accommodations during the recruitment process, please let us know—we’re here to support you.

We thank all applicants for their interest. Only those selected for an interview will be contacted.