Director, Software Engineering & AI

Andar Software•Oakville, ON

7d•CA$150,000 - CA$160,000•Remote

About The Position

At Andar Software, we build integrated technology that powers nonprofits to drive real, lasting change. Our product suite helps United Ways and other not-for-profit organizations across North America raise and distribute donations, manage donor relationships, run marketing campaigns, coordinate events, recruit volunteers, and more. We’re proud to be the engine behind some of the most impactful organizations in the sector. Originally based in Markham, ON, Canada; Andar has evolved into a fully remote organization. Role Overview: 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.

Requirements

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
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
Strong execution focus with a drive for results
Able to balance speed, quality, and technical sustainability
Comfortable operating in a multi-product, partially legacy environment
Data-driven decision maker with strong business alignment.
Effective communicator across technical and non-technical audiences

Nice To Haves

Experience operating in mission-driven or social sector is an asset

Responsibilities

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
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
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
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
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)
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