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Director of Software Development

Job in Toronto, Ontario, C6A, Canada
Listing for: LilYPad POS
Full Time position
Listed on 2026-02-19
Job specializations:
  • Software Development
    Cloud Engineer - Software, DevOps, Full Stack Developer, Software Engineer
Salary/Wage Range or Industry Benchmark: 140000 - 155000 CAD Yearly CAD 140000.00 155000.00 YEAR
Job Description & How to Apply Below

Job Description:

Compensation:
The expected salary range for this role is between $140,000 and $155,000, depending on experience and qualifications.

Reason for Opening:
Net New position

AI is used to screen, assess, or select applicants for this role.

Overview

We are seeking a hands‑on Director of Software Development to lead the design, development, and delivery of next‑generation software products. This individual will combine strong technical expertise with leadership skills to implement agile processes, modernize architecture, and guide a small but high‑impact development team toward predictable, scalable, and high‑quality delivery.

You will play a pivotal role in shaping both the product and engineering culture — balancing execution with strategy. Initially, you’ll contribute directly to the codebase, especially around architectural foundations, frameworks, and development standards.

Key Responsibilities Leadership & Process
  • Establish and lead agile development processes (Scrum/Kanban), implementing sprint planning, retrospectives, and velocity tracking.
  • Define and enforce engineering best practices, including coding standards, peer reviews, documentation, and CI/CD integration.
  • Mentor developers and foster a culture of accountability, continuous improvement, and innovation.
  • Partner closely with Product Management and Operations to translate business goals into technical plans and deliverables.
  • Own the end‑to‑end SDLC and drive measurable improvements in quality, reliability, and time‑to‑market.
Technical Ownership
  • Lead architectural and framework decisions across the stack (frontend, backend, APIs, database, integrations).
  • Design and evolve scalable, maintainable, and secure application architectures.
  • Contribute code to critical components, especially in early‑stage architecture and core system design.
  • Guide database schema design, performance optimization, and data integrity practices.
  • Collaborate with Dev Ops to enhance CI/CD pipelines, cloud deployment automation, and environment consistency.
  • Drive adoption of testing frameworks, unit testing, and automated QA pipelines.
Strategic Contribution
  • Build and scale a high‑performing team aligned with business growth and product strategy.
  • Participate in long‑term architectural planning and technology roadmap development.
  • Evaluate emerging technologies and tools to improve productivity and maintain technical competitiveness.
  • Partner with leadership on capacity planning, budgeting, and risk mitigation for ongoing and future initiatives.
Required Qualifications
  • 10+ years of professional software development experience, including 3+ years in a leadership role (Tech Lead, Architect, or Director).
  • Proven experience designing and delivering full‑stack web applications (front‑end frameworks like Angular, React, or Vue + back‑end such as Node.js, Python/FastAPI, .NET, or Java).
  • Strong architectural, design, and database modeling skills (SQL and/or No

    SQL).
  • Demonstrated success implementing or maturing Agile processes within small to midsized teams.
  • Hands‑on experience with CI/CD pipelines, version control (Git), and deployment automation.
  • Strong understanding of software quality practices including automated testing and code reviews.
  • Excellent communication and leadership skills; ability to balance technical depth with business context.
Nice‑to‑Have Qualifications
  • Experience with AWS cloud services (EC2, RDS, S3, Cloud Front, ECS/EKS, etc.).
  • Background in test automation frameworks (e.g., PyTest, Jest, Cypress, Selenium, or similar).
  • Familiarity with containerization and orchestration (Docker, Kubernetes).
  • Experience with observability tools (Grafana, Prometheus, Datadog, etc.).
  • Prior SaaS, multi‑tenant, or high‑availability system experience.
Personal Attributes
  • Pragmatic, execution‑driven, and comfortable being “hands‑on.”
  • Collaborative and able to mentor without micromanaging.
  • Strong systems thinker — able to design for both current needs and future scalability.
  • Passionate about improving process maturity, code quality, and team culture.
  • Thrives in fast‑paced environments with small, cross‑functional teams.

Updated the requisition with Compensation details per the Canada legislation…

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