Principal Software Developer - Cloud Platform

at  CaseWare

Job Title: Principal Software Developer – Cloud Platform
Reporting to: Craig Thorvardson, Director of Software Development, Cloud Platform
Location: Hybrid (3 days WFO in GTA). 351 King St E, Toronto, ON \uD83C\uDDE8\uD83C\uDDE6
Contact: Chengeer Lee - Principal Talent Acquisition Partner & Coach
About the Role:
We are looking for a Principal Software Developer to lead the technical vision and roadmap for Caseware’s Cloud Platform team, which powers our core Caseware Cloud product—a critical suite for practice management and client collaboration. In this role, you will drive architectural decisions, oversee major technical initiatives, and work with cross-functional teams to scale and enhance the platform’s performance, reliability, and maintainability.
This role is crucial for bridging the gap between Cloud Platform Engineering and development teams, ensuring a balance between maintaining the current monolith (written in .NET) and progressively introducing microservices architecture (Java and .NET Core). You’ll work closely with engineering and product leaders to support technical depth, quality engineering, and cultural engagement while enabling long-term business growth.

• Architectural Leadership: Lead the evolution of the Cloud Platform from a monolith to microservices, identifying the most impactful initiatives that provide the highest return on investment.
• Stakeholder Collaboration: Work closely with engineering, product teams, and executive leadership to develop a robust technical strategy that aligns with the company’s broader goals.
• Technical Vision & Strategy: Drive long-term planning and vision for the Cloud Platform, contributing to both monolith and microservices architectures. Ensure effective resource allocation and priority-setting for key projects.
• Quality Engineering Advocacy: Establish and promote a quality-first engineering culture, guiding teams to implement testing and quality assurance right from the development phase, shifting from end-to-end testing to more modern practices.
• Team Leadership & Mentorship: Inspire and mentor development teams, helping them improve their technical skills, enhance their understanding of quality engineering, and foster a positive team culture.
• Hands-On Involvement: Balance technical leadership with hands-on coding and architectural design. Assist in incident response management and participate in critical production outages.
• Project Management: Lead the execution of major projects such as EKS migration, observability improvements, and enhancements to SQL database performance.