Director of Software Engineering & AI

Role Description

As the Director of Software Engineering & AI, you will lead our core R&D organization and drive the next phase of innovation across our Andar/360 product suite. This role is responsible for engineering execution, architecture, and technical strategy, with an added mandate to embed AI capabilities across our platform to enhance customer value and operational efficiency. The role operates in close partnership with Product Management, which owns product vision and roadmap, while this position ensures high-quality, scalable, and predictable delivery.

You will be playing a pivotal role in strategic decisions as a core member of the executive leadership team, reporting to the General Manager, and overseeing the R&D team of approx. 8 FTE.

Key Responsibilities

• Engineering Leadership & Delivery
  • Lead and develop the software engineering team (development, QA, DevOps)
  • Own delivery execution, including sprint planning, resourcing, and timelines
  • Drive improvements in engineering velocity, predictability, and quality
  • Establish and enforce development best practices, standards, and governance
• Technical Strategy & Architecture
  • Define and evolve the technical architecture of Andar/360 and supporting systems
  • Ensure systems are scalable, secure, and maintainable
  • Manage technical debt and modernization initiatives
  • Guide build vs. buy decisions in partnership with Product and leadership
  • Own the security and data privacy posture of the platform, ensuring compliance with applicable frameworks (e.g., SOC 2, PIPEDA, CASL) and donor data protection obligations
• AI & Innovation Leadership
  • Define and lead Andar’s AI strategy across products and internal operations of R&D
  • Identify opportunities to embed AI to enhance product capabilities and engineering efficiency, including:
    • Donor and campaign analytics
    • Workflow automation
    • Customer insights and reporting
  • Partner with Product Management to deliver AI-enabled features into the roadmap
  • Evaluate tools, platforms, and partnerships to accelerate AI adoption
  • Establish engineering best practices for AI development, governance, and responsible use
• Cross-Functional Collaboration
  • Partner closely with Product Management on technical execution and roadmap prioritization trade-offs
  • Collaborate with:
    • Customer Care (supportability and issue resolution)
    • Operations (implementation efficiency)
    • Finance (cost management and ROI alignment)
  • Act as a key stakeholder in customer-impacting technical decisions
  • Manage vendor and technology partner relationships, including contract oversight and performance evaluation
  • Represent engineering at the executive level; provide regular updates to the General Manager on engineering strategy, risks, and delivery progress
• Operational Excellence
  • Improve DevOps maturity, CI/CD practices, and release management
  • Ensure high system reliability and uptime in coordination with hosting teams
  • Reduce production issues and improve response/resolution times
  • Build metrics-driven engineering management (velocity, defects, cycle time)
• Team Development & Leadership
  • Coach and mentor engineering leaders and team members
  • Foster a culture of accountability, collaboration, and continuous improvement
  • Support hiring, retention, and succession planning
  • Build a scalable org structure aligned to company growth

Qualifications

• Bachelor’s degree in computer science or equivalent experience
• Experience with the following:
  • Legacy platform: Java (Swing desktop + Servlets/JSP web tier), MSSQL Server
  • Modern frontend: React, TypeScript, Tailwind, AWS Amplify/Cognito
  • AI backend: Node.js + TypeScript, AWS Lambda, AWS Bedrock, PostgreSQL
  • Cloud microservices: Python, FastAPI, Pydantic, Docker, JWT
• 5–10 years in software engineering, including 3+ years in senior leadership roles with direct management of multi-team engineering organizations (10+ engineers)
• Proven experience leading engineering teams in SaaS or enterprise software environments
• Broad technology fluency across cloud platforms, SaaS architecture, APIs, and modern development practices; comfortable evaluating technology stacks without being prescriptive
• Demonstrated ability to scale teams and improve delivery performance
• Strong understanding of modern architecture patterns and cloud-based systems
• Hands-on experience implementing AI/ML capabilities in a product environment, including LLM integration, AI-assisted workflows, or predictive analytics; familiarity with AI governance, responsible AI practices, and evaluating AI vendor platforms
• Track record of working effectively within a Product + Engineering partnership model
• Experience operating in mission-driven or social sector is an asset
• Budget and resource planning
• Demonstrated experience leading legacy system modernization — migrating or re-platforming production systems while maintaining continuity
• Working knowledge of data privacy and security compliance requirements relevant to Canadian and North American SaaS operations (PIPEDA, CASL, SOC 2) is an asset

Benefits

• Competitive salary commensurate with experience (CAD $150K-$160K)
• Performance-based bonus
• Comprehensive benefits package including health, dental, and vision
• Flexible vacation and paid time off

Work Arrangement

• Fully remote; Andar operates across North American time zones with core collaboration hours in Eastern Time
• Occasional travel required for team offsites, leadership meetings, and customer engagements