Principal Software Engineer - AI Accelerated

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes with industry leading products and platforms developed through an AI-Driven Software Development Life Cycle.

ABOUT US

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric—with AI embedded across the automation lifecycle—Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.

CORE VALUES

• One Team. One Redwood
• Make Your Own Weather
• Obsess over Customer Success
• Work the Problem
• Be Curious
• Own the Outcome
• Respect Each Other
  
  

YOUR IMPACT

As a Principal Software Engineer, you will be a senior technical leader and strategic influencer shaping Redwood’s RunMyJobs platform. You will drive high-impact technical decisions, own complex system designs, and lead initiatives that span teams and domains. Your work will translate business needs into scalable, resilient full-stack solutions that meet both functional and non-functional requirements. 

In this fast-paced, agile environment, you will lead projects from concept through delivery, collaborating closely with product, design, engineering, finance, and customer success teams to ensure alignment and success. You will set the standard for engineering excellence by mentoring engineers at all levels and championing a culture of continuous improvement, innovation, and technical rigor.

A key part of this role is to ensure development teams follow best practices, coding standards, and technical requirements. You will provide hands-on technical guidance and architectural direction, including code and design reviews, while creating and maintaining design and code standards. Understanding, communicating, and enforcing Redwood’s software architecture strategy will be fundamental. 

You will proactively identify critical technical challenges related to quality, scalability, observability, and performance. By spotting early risks in architecture or implementation, you help prevent issues before they affect delivery or user experience. Leveraging data analysis, code reviews, and collaboration with cross-functional teams, you ensure that solutions are robust, efficient, and scalable, driving Redwood’s platform forward with confidence.

You will work directly with the Engineering manager for your teams and collaborate closely with Redwood’s Architecture team to ensure technical alignment, consistency, and strategic direction across the platform. As a key member of the engineering leadership group, you will influence architectural decisions and contribute to the evolution of our engineering strategy.

This is a senior individual contributor role with broad technical ownership and no direct people management responsibilities.

Your responsibilities will also include:

• System Architecture & Design: Lead the design and implementation of large-scale distributed systems, focusing on resilience, low-latency, and fault tolerance within the Java ecosystem.
• Prompt Engineering for SDLC: Apply advanced prompt engineering techniques to maximize the efficacy of generative AI tools for writing comprehensive unit/integration tests, drafting technical documentation (Javadoc, API specs), and generating code refactoring suggestions.
• CI/CD and Observability: Oversee and enhance automated build, test, and deployment pipelines (CI/CD, Kubernetes/Docker) in a cloud environment (AWS/Azure/GCP), leveraging AI tools for proactive anomaly detection and monitoring.
• Collaborating with the product management team to define, design, and implement new functionality that enhances Redwood's software solutions.
• Diagnosing and resolving complex technical challenges and system issues to ensure platform reliability.

YOUR EXPERIENCE

The ideal candidate will have a Bachelor's or Master's degree in Computer Science, Software Engineering, or a related field. You should have over eight years of software development experience, with at least three to five years in a senior or staff software engineer role. This position requires proven experience in workload automation, job scheduling, and orchestration technologies.

• Deep proficiency in Java (11/17+), with strong experience in modern frameworks and libraries.
• Strong background in microservice architecture, containerisation (Docker, Kubernetes) and RESTful API design.
• Experience with frontend technologies including ReactJS, MobX, and TypeScript.
• Knowledge of cloud platforms such as AWS, Azure, and Google Cloud.
• Strong understanding of database technologies (SQL, NoSQL, data modelling).
• Familiarity with DevOps practices and CI/CD pipelines.
• Familiarity with tools like Git, GitHub, Jira and Bamboo from Atlassian.
• Proficiency in testing frameworks such as JUnit, Jest and Playwright with a focus on driving quality automation and testability by design.
• Commitment to engineering best practices, including code reviews, static analysis and continuous quality improvements.
• AI Tool Fluency: Demonstrated ability to proficiently use AI-powered developer tools (e.g., GitHub Copilot, Claude Code, CodeWhisperer) in a production environment.
• Code Judgment: Proven track record of evaluating and overriding AI-generated suggestions that are technically correct but architecturally flawed or non-compliant with security and performance best practices.
• Prompting Proficiency: Experience writing clear, contextual, and effective prompts for generative AI to produce usable code, tests, or documentation.
• Adaptability & Learning: High degree of curiosity and a proactive approach to learning new AI tools and techniques that continuously reshape the development workflow.
• Domain & Architectural Focus: The capacity to abstract away from low-level coding details to focus on high-value business logic and systemic architectural integrity.

Pay Transparency: The typical base salary range for this position is CAD $150,000- $170,000 annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Vacancy Status: Existing vacancy

AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.