Principal Software Developer - Cloud Platform

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 🇨🇦

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.

What is Caseware Cloud?

Caseware Cloud is a flagship cloud-based platform focused on practice management and client collaboration, offering tools that streamline the way professionals and firms manage their engagements and client relationships. Caseware Cloud underpins this suite, providing the infrastructure, scalability, and performance needed for seamless operations across teams and practices. This role is pivotal to ensuring that the Cloud Platform continues to evolve, supporting our rapid growth and future business needs.

Why This Role Matters:

The Cloud Platform team is responsible for long-term planning and ensuring the platform’s success.A strong leader is needed to optimize technical decisions, reduce technical debt, and build a clear technical roadmap. You will provide leadership, vision, and mentorship to the team, ensuring the adoption of best practices and driving innovation across the platform.

A quick message from your Talent Partner:

https://www.loom.com/share/297c5629e8a44999933f40376ba122bd?sid=27ada6c1-b23a-452b-9a50-a3790142eaf2

What you will do:

• 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.

What you will bring:

• 10+ years of software development experience, with a proven track record of leading and delivering cloud-based platform solutions.
• Strong .NET expertise, with hands-on experience in .NET Framework, .NET Core, and familiarity with Java for microservices architecture.
• Deep understanding of SQL databases, with experience in optimizing SQL performance at scale. NoSQL experience is a plus.
• Hands-on experience in building, scaling, and maintaining cloud applications on AWS, preferably within large-scale distributed systems.
• Leadership experience guiding teams through architecture decisions, technical debt reduction, and improving development velocity and culture.
• Incident management expertise, especially in handling outages, improving system reliability, and contributing to continuous improvement in platform availability.
• Familiarity with DevOps practices, CI/CD pipelines, and cloud-native development.
• Excellent communication skills, with the ability to collaborate across teams and provide technical insight to executive leadership.
• Experience driving quality engineering initiatives and fostering a culture that emphasizes proactive testing and reliability.

Key Success Factors in 6-12 Months:

• Technical Roadmap: Develop and execute a roadmap that reduces technical debt, optimizes the Cloud Platform’s architecture, and enhances system performance.
• Cross-Team Collaboration: Build strong relationships with product and platform leaders, ensuring seamless collaboration and alignment with broader company objectives.
• Quality Engineering Culture: Establish new testing patterns that shift quality efforts earlier into the development lifecycle, reducing production issues.
• Mentorship & Leadership: Develop and mentor a high-performing development team, instilling best practices and guiding the next generation of technical leaders.
• Business Case Contributions: Lead at least one high-value business case within the first six months, demonstrating impact and delivering results.

What’s In It for You:

• Architectural Ownership: Drive the technical transformation of a mission-critical platform supporting global practice management solutions.
• Strategic Influence: Shape the future of the Cloud Platform through high-level technical decisions that directly influence the company’s success.
• Mentorship & Growth: Lead and mentor a talented team of developers, helping to foster a culture of technical excellence.
• Work-Life Balance: Enjoy competitive compensation, comprehensive benefits, and a hybrid work model that offers flexibility and work-life balance.

This role provides a unique opportunity for a seasoned software architect and leader who wants to make a direct impact on the future of cloud-based practice management solutions at Caseware. If you are passionate about cloud-native technologies, quality engineering, and team culture, we encourage you to apply.