Principal Software Developer

Job Title: Principal Software Developer – Smart Engagements (SE) Platform

Reporting to: Andrew Allen, VP of Software Development, SE Platform

Location: Hybrid (3 days WFO in GTA). 351 King St E, Toronto, ON 🇨🇦

We are seeking a Principal Software Developer to drive the technical vision and architectural strategy of Caseware’s Smart Engagements (SE) Platform. As part of our core cloud offering, the SE Platform powers cloud-based audit and engagement workflows. In this role, you will lead the architectural transformation from a monolithic to a highly scalable microservices-based environment, contributing directly to the platform’s ability to support future business growth.

This is a key leadership role in a newly formed team structure, where you will act as a hands-on architect while mentoring the development team, guiding the long-term technical vision, and contributing to crucial platform projects like scaling systems, improving observability, and supporting critical migrations.

Contact:

Chengeer Lee - Principal Talent Acquisition Partner & Coach

A quick message from your Talent Partner:

https://www.loom.com/share/da7e447205594e289b64221d952931c3?sid=ed4e7608-efaf-4052-aec1-eb88fe2d6fc5

What you will do:

• Lead the architectural transformation: Define and execute the technical strategy to evolve the SE platform from a synchronous monolith to a scalable, distributed system.
• Establish architecture patterns: Prototype and implement best practices for distributed systems design, ensuring smooth transitions to microservices, optimized AWS usage, and future-proof system architecture.
• Oversee key platform projects: Contribute heavily to the MongoDB to DocumentDB migration and support dynamic auto-scaling improvements to our EKS services.
• Mentor and lead: Guide teams in delivering projects, fostering a mentorship culture, and ensuring adherence to high standards in coding, design, and cloud-native development.
• Drive best practices: Collaborate with R&D groups to implement best practices for asynchronous communication and system integration, improving scalability and efficiency.
• Architect for observability: Implement and oversee system health monitoring using platforms like New Relic or Data Dog, ensuring performance, reliability, and scalability are maintained across the platform.

What you will bring:

• 10+ years of experience in software development, with at least 5 years in a senior technical leadership role, preferably as a Principal or Staff Developer.
• Deep experience with distributed systems architecture and cloud-native development on AWS, including expertise in EKS, SQS/SNS, Lambda, and DocumentDB.
• Proven ability to architect and scale cloud platforms, guiding teams in building microservices and distributed systems.
• Strong technical leadership: Experience mentoring teams, setting development standards, and influencing the technical direction across multiple teams.
• Hands-on experience with observability platforms such as New Relic or Data Dog to monitor system health, performance, and reliability.
• Proficiency in Java backend development with familiarity in frontend technologies like Angular.
• Experience working with DevOps teams, CI/CD pipelines, and cloud infrastructure to deliver scalable, resilient platforms.
• Communication and collaboration skills to align cross-functional teams and engage with senior leadership on technical strategy.

Key Success Factors in 6-12 Months:

• Establish a solid technical strategy: Collaborate with SE Platform leadership to define the platform’s technical direction, ensuring alignment with business growth and scalability objectives.
• Deliver architecture prototypes and patterns: Build and document key architecture patterns that guide the team in transforming the monolithic system to microservices.
• Support key platform migrations: Contribute significantly to the MongoDB-to-DocumentDB migration and lead improvements in the scalability and performance of EKS services.
• Mentor and guide teams: Cultivate a high-performing development team, ensuring the adoption of best practices for coding, architecture, and cloud-native design.

What’s In It for You:

• Architectural Ownership: Lead the transformation of a mission-critical, globally-used cloud platform, directly shaping its future technical direction. Your decisions will modernize Caseware’s architecture and impact how we deliver solutions to clients worldwide.
• Strategic Influence: Collaborate with senior leadership to guide the SE Platform’s growth and ensure alignment with business objectives, contributing to high-level technical discussions that influence Caseware’s broader technology roadmap.
• Cutting-Edge Technology: Work with advanced AWS technologies, modern cloud infrastructure, and observability tools like New Relic and Data Dog. You’ll be at the forefront of cloud-native development, tackling complex, large-scale challenges and driving continuous innovation.
• Leadership & Mentorship: Develop and guide the next generation of technical leaders, fostering a culture of technical excellence across multiple teams. Your mentorship will shape both the team’s success and the technical practices that drive the platform forward.
• Growth & Innovation: Thrive in a culture that encourages exploration of new ideas and values continuous learning. You’ll have the autonomy to push boundaries, driving innovation and contributing to Caseware’s growth strategy.
• Top-Tier Compensation: Enjoy a competitive salary, comprehensive benefits, and a focus on work-life balance, with ample opportunities for professional development and career advancement.