Director Engineering

Redwood Software; Canada; On-site; CAD 180,000 - 260,000; Full time

Job summary

Redwood Software seeks a Director of Engineering - AI & Full-Stack SaaS to steer engineering strategy and execution for a scalable enterprise SaaS platform in Canada. You will lead multiple teams across backend, frontend, APIs and AI adoption, shaping architecture, standards and delivery while embedding AI across the SDLC.

The role requires 15+ years in software/product engineering, proven multi-team leadership, and strong cloud-native / enterprise SaaS experience.

Qualifications

• Minimum 15+ years in software/product engineering with leadership experience.
• Proven track record leading large multi-team engineering organizations.
• Extensive enterprise SaaS product development experience.
• Strong background in full-stack software engineering and modern architecture.
• Experience with Java/Spring Boot or comparable enterprise backend tech.
• Deep understanding of microservices, APIs, distributed systems and cloud-native architectures.
• Hands-on experience with AWS, Azure or GCP.
• Experience with DevOps, CI/CD and engineering productivity practices.
• Demonstrated AI/GenAI adoption within software engineering or enterprise products.

Responsibilities

• Lead and mentor multiple engineering teams delivering enterprise SaaS products.
• Define and execute engineering strategy, roadmap, architecture and standards.
• Drive scalable, secure, reliable cloud-native SaaS applications.
• Provide technical leadership across backend, frontend, APIs and microservices.
• Drive adoption of AI/GenAI across development lifecycle and automation.
• Collaborate with Product, Architecture, DevOps and Security teams.
• Establish best practices for design, coding, testing, CI/CD, observability and reliability.
• Own delivery, quality, scalability and operational excellence across product areas.
• Resolve complex technical and architectural challenges.
• Foster a culture of innovation, ownership, collaboration and continuous improvement.
• Evaluate emerging technologies to leverage AI to boost productivity and product capabilities.
• Drive modernization of existing enterprise platforms.

Skills

15+ years experience

Large multi-team leadership

Enterprise SaaS product development

Full-stack software engineering

Java / Spring Boot backend

Microservices & distributed systems

Cloud-native architectures

AWS / Azure / GCP

DevOps / CI/CD

AI/GenAI adoption

Architectural problem-solving

Leadership and stakeholder management

Tools

AWS

Azure

GCP

Job description

About the Role

We are looking for a Director of Engineering - AI & Full-Stack SaaS to lead the engineering strategy and execution for a highly scalable, enterprise-grade SaaS platform.

This role is ideal for a strong engineering leader who combines deep software engineering expertise, enterprise SaaS experience, cloud-native architecture, full-stack product development, and practical AI/GenAI adoption.

The successful candidate will lead multiple engineering teams, drive architectural and technical decisions, improve engineering velocity and quality, and help embed AI across the software development lifecycle and product engineering ecosystem.

Key Responsibilities

• Lead and mentor multiple engineering teams responsible for building and delivering enterprise SaaS products.
• Define and execute the engineering strategy, technical roadmap, architecture and development standards.
• Drive development of highly scalable, secure, reliable and cloud-native SaaS applications.
• Provide technical leadership across backend, frontend, APIs, microservices and distributed systems.
• Drive adoption of AI/GenAI tools and capabilities across the engineering lifecycle, including development, testing, code quality, productivity and automation.
• Partner closely with Product, Architecture, DevOps, Security and other cross-functional teams to deliver business-critical capabilities.
• Establish engineering best practices around design, coding, testing, CI/CD, observability, performance and reliability.
• Own engineering delivery, quality, scalability and operational excellence across multiple product areas.
• Identify and resolve complex technical and architectural challenges.
• Build a high-performing engineering culture focused on innovation, ownership, collaboration and continuous improvement.
• Evaluate emerging technologies and identify opportunities to leverage AI and automation to improve engineering productivity and product capabilities.
• Drive technical modernization and evolution of existing enterprise platforms.
• Communicate technical strategy, risks, priorities and progress effectively to senior leadership and stakeholders.

Required Skills & Experience

• 15+ years of experience in software/product engineering, with significant experience in engineering leadership roles.
• Proven experience leading large/multi-team engineering organizations.
• Strong background in enterprise SaaS product development.
• Excellent understanding of full-stack software engineering and modern application architecture.
• Strong experience with Java / Spring Boot / or comparable enterprise backend technologies.
• Strong understanding of microservices, APIs, distributed systems and cloud-native architectures.
• Hands-on experience with AWS, Azure or GCP.
• Experience building and scaling highly available, secure and resilient SaaS platforms.
• Strong understanding of modern frontend technologies and full-stack development practices.
• Experience with DevOps, CI/CD, automated testing and engineering productivity practices.
• Demonstrated experience adopting or implementing AI/GenAI technologies within software engineering or enterprise products.
• Strong architectural and technical problem-solving capabilities.
• Excellent people leadership, stakeholder management and communication skills.

Good to Have

• Experience with LLMs, Generative AI, AI agents or AI-powered developer tools.
• Experience integrating AI into enterprise SaaS products.
• Experience driving AI-assisted software development / AI-first SDLC
• Experience with workflow automation, orchestration or enterprise automation platforms.
• Experience working with mission-critical enterprise applications.
• Experience managing geographically distributed engineering teams.
• Strong exposure to product-led engineering environments.

Ideal Candidate

The ideal candidate is a technology and people leader , rather than an AI researcher alone. They should have a strong track record of building and scaling enterprise software teams and products, while also demonstrating the ability to identify practical AI opportunities and integrate AI into modern engineering and SaaS product development.

Candidates from enterprise SaaS, cloud platforms, automation, workflow, IT management, enterprise software and AI-enabled product companies would be particularly relevant.

If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!

THE LEGAL BIT

Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero tolerance policy applied to it.
Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at [e-mail]