Director, Software Engineering & AI at Andar Software – Canada - Ontario | Jobyssey

Job Summary:

Job Description:

CAD$150K-CAD$160KDirector of Software Engineering & AI – Job Description

About us:

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.

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

Key Success Metrics

Delivery predictability (on-time, on-scope releases)

Product quality (defect rates, production stability)

Engineering velocity and throughput

Reduction in technical debt

Successful rollout of AI-enabled features

Team engagement and retention

Budget Ownership

Qualifications & Experience

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

Leadership Profile

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

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

Compensation & 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

Worker Type:

Regular

Number of Openings Available:

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