Principal Software Developer (Java /.NET)

What is Caseware Cloud?

Caseware Cloud is the foundation of Caseware’s cloud-based solutions, designed to streamline practice management and client collaboration for accounting firms and professional services. It provides secure, scalable, and integrated tools that help firms manage engagements, collaborate with clients, and maintain compliance with industry standards.

Cloud Collaborate Platform

Caseware Cloud Collaborate is a core component of Caseware Cloud, specifically focused on client collaboration and document exchange. It enables firms to securely communicate with clients, request and share documents, track progress, and ensure efficient workflows.

Key aspects of Cloud Collaborate include:

•Secure Client Portals – A centralized, encrypted space for firms and their clients to share documents, messages, and updates.

•Workflow Automation – Automates document requests, approvals, and follow-ups to improve efficiency.

•Integration with Caseware Cloud Apps – Seamlessly connects with other Caseware solutions, ensuring a unified experience.

•Scalability & Performance – Designed for global firms, handling large-scale data exchanges with robust AWS-backed infrastructure.

As Caseware modernizes its platform, Cloud Collaborate plays a key role in evolving from a .NET monolith to a microservices-based architecture. This transformation aims to enhance performance, security, and future scalability, making it more flexible and efficient for firms of all sizes.

About the Role:

We are looking for a Principal Software Developer to lead the architectural evolution of Caseware’s Cloud Platform, which powers our core Caseware Cloud product—a mission-critical suite for practice management and client collaboration.

In this role, you will design and implement microservices in Java, migrate functionality from a .NET monolith, and ensure our cloud platform is scalable, secure, and maintainable. While .NET expertise is not required, you must be comfortable reading .NET code to understand the existing architecture and successfully guide the transition to a Java-based microservices ecosystem.

This role is a blend of technical leadership, hands-on coding, and mentorship, ensuring our engineering teams adopt best practices in cloud architecture, security, and quality engineering.

If you’re a Java architect with hands-on coding experience, expertise in AWS and microservices, and a passion for mentorship and cloud transformation, we’d love to hear from you.

Location: Hybrid (3 days WFO in GTA), Toronto, ON

Reporting to: Craig Thorvardson, Director of Software Development, Cloud Platform

Contact:

Chengeer Lee - Principal Talent Acquisition Partner & Coach

What You Will Do:

• Lead the migration from a .NET monolith to Java microservices, designing scalable and secure cloud-native solutions.
• Build authorization and authentication microservices as part of a tech enablement strategy.
• Drive API-first development for seamless integration across Caseware’s platform.
• Design scalable solutions that support AWS Elastic Kubernetes Service (EKS).
• Write production-quality Java code and develop proof of concepts (POCs) to validate new technology decisions.
• Debug and troubleshoot complex production issues, ensuring platform reliability.
• Collaborate on AWS infrastructure configurations, CI/CD pipelines, and observability improvements.
• Mentor senior developers and tech leads on microservices, cloud architecture, and security best practices.
• Provide guidance to teams struggling with debugging, performance tuning, and architectural decision-making.
• Work closely with distributed teams across Canada, the Netherlands, and Romania to drive architectural excellence.
• Optimize SQL Server performance as we migrate to a microservices-based architecture.
• Work closely with DevOps to ensure scalable and secure cloud-native deployments on AWS.
• Influence CI/CD and cloud security best practices.
• Partner with engineering leaders and product teams to align technical decisions with business objectives.
• Support future tech acquisitions, evaluating integration strategies for acquired products.
• Contribute to sunsetting legacy applications through a phased API migration approach.

What you bring:

• 10+ years of software development experience, with deep expertise in Java and cloud-native architectures.
• Experience with microservices design, distributed systems, and API-first development.
• Comfortable reading .NET code to understand legacy architecture while driving Java microservices adoption.
• Strong AWS experience, particularly with EKS, Cognito, IAM, Lambda, and API Gateway.
• SQL expertise, particularly with SQL Server and experience migrating databases from monolithic to microservices.
• Identity and access management (IAM) expertise, with experience in Auth0, Keycloak, or AWS Cognito.
• Experience mentoring teams, improving code quality, and enforcing architectural best practices.
• Deep understanding of DevOps, CI/CD, and automated testing methodologies.
• Exceptional problem-solving and debugging skills, with the ability to lead technical initiatives across teams.

Key Success Factors (First 6-12 Months)

• Microservices Architecture: Successfully design, prototype, and build new Java-based services.
• Scalability & Security: Implement solutions that scale securely on AWS, ensuring high availability.
• Tech Mentorship: Establish yourself as the go-to expert for Java microservices and security best practices.
• Sunsetting Legacy Systems: Develop an API strategy to gradually phase out legacy products.
• Quality Engineering Leadership: Drive best practices for test automation and developer-led quality efforts.

What's in it for you:

• Architectural Ownership: Drive the transformation of a mission-critical platform.
• Hands-On Leadership: Get the balance of high-level decision-making and hands-on coding.
• Strategic Influence: Play a key role in shaping Caseware’s technology direction.
• Hybrid Work Model: Work from home with 3 days in-office in Toronto.
• Strong Team & Vision: Collaborate with engineering leaders and a strong CTO to drive innovation.