Software Development Manager - RunMyJobs, 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

Redwood Software delivers powerful automation solutions that simplify and accelerate critical business and IT processes for some of the world’s largest enterprises. The Redwood Automation Platform streamlines complex business workflows and operations, reduces manual effort, ensures compliance, and accelerates business outcomes through intelligent, cloud-native automation.

As Software Development Manager, Redwood Automation Platform, you will lead multiple development teams and you’ll report to the Head of Engineering for Redwood’s core product platform at our Toronto based Engineering hub. You’ll help to shape the technical strategy, scale engineering operations, and lead an engineering team building and evolving our SaaS-based business process automation platform that serves as the foundation for multiple Redwood products, solutions, and services. This is a high-impact role, requiring strong technical depth, leadership, and a passion for delivering world-class enterprise software.

• Partner with the Head of Engineering to help provide technical leadership for Redwood’s core RunMyJobs products and services.
• Collaborate closely with Product Management, Sales, Customer Success, and executive leadership to align engineering priorities with business goals.
• Improve engineering processes for Agile product development, continuous delivery, and cloud-native development.
• Lead, mentor, and develop engineers supporting career growth and succession planning.
• 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.
• Partner with stakeholders to manage team capacity, hiring, and resource allocation as Redwood’s product portfolio grows.
• Track and report on key engineering KPIs related to delivery velocity, product quality, and operational performance.

 

YOUR EXPERIENCE 

• 6+ years of software development experience, with exposure coaching and or leading software developers.
• Proven success building and scaling enterprise SaaS products, ideally in automation, ERP,  or workflow orchestration domains.
• Strong technical background in backend software development (e.g., Java or similar languages), distributed systems, and RESTful APIs.
• Experience leading teams building cloud-native applications on platforms like AWS, Azure, or GCP.
• Track record of leading Agile software development processes and cross-functional product delivery.
• Experience in operationalizing DevOps, CI/CD pipelines, and continuous cloud delivery best practices.
• AI Tool Fluency: Demonstrated ability to proficiently use AI-powered developer tools (e.g., GitHub Copilot, 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 $135,000- $160,000 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.