Quick Summary
Head of Software Engineering (Remote Canada, $130k–$150k CAD) sought to lead technical vision, architecture, and a growing team across two primary product stacks: Rails/React and PHP/WordPress/LAMP. This hands-on leadership role requires 5+ years of engineering leadership experience, deep expertise in AWS (Fargate, Lambda, Docker), fluency in a major backend language (Ruby, PHP, Python), and strong technical breadth to oversee multi-stack teams. A critical focus is championing and implementing AI strategy across product features and internal tooling, alongside overseeing DevOps, CI/CD pipelines, and security compliance initiatives.
Head of Software Engineering – AI Strategy & AWS | Remote Canada ($130k – $150k CAD)
Department: Engineering
Reports to: CEO
Term: Full-Time Permanent
Primary Location: Remote in Canada
Salary Range: $130,000 – $150,000 CAD
Join Wicket, a remote-first Canadian company pioneering the future of association technology. We are seeking a hands-on Head of Software Engineering to lead our growing team, define our technical vision, and drive the development of our groundbreaking products: Wicket Member™ (Member Data Platform built on Rails/React) and Wicket Web™ (WordPress/WooCommerce platform).
Responsibilities of this Role:
Technical Leadership & Architecture
- Own the technical direction and architecture across Wicket Member™ and Wicket Web™.
- Ensure products are scalable, maintainable, secure, and performant.
- Drive engineering best practices across code quality, testing, documentation, and automation.
AI Strategy & Enablement
- Champion the adoption of AI across the organization, from product features to internal developer tooling.
- Stay current on AI/ML advancements and identify integration opportunities into Wicket’s offerings.
- Collaborate with Product to prototype and implement AI-driven features that deliver customer value.
Hands-On Contribution
- Contribute directly to the codebase for experimentation, especially on architecture-heavy or complex projects.
- Review code and guide implementation decisions, focusing on long-term maintainability.
- Debug, unblock, and elevate the work of the software engineering team.
Team Leadership & Development
- Lead and support a growing team of developers across multiple product stacks.
- Manage the technical customer support team and establish efficient processes for handling support, customization, and product requests.
- Mentor and develop software engineers and support staff through coaching and growth planning.
- Foster a collaborative and inclusive software engineering culture built on trust and autonomy.
Infrastructure, DevOps & Compliance
- Oversee DevOps practices, CI/CD pipelines, and internal tooling for both LAMP and API-first Rails Application/React Admin SPA stacks.
- Ensure systems are observable, secure, and easy to deploy and maintain.
- Lead initiatives towards security and data privacy compliance (e.g., SOC2, SSDF, or ISO/IEC 27001).
Required Technical Knowledge and Experience:
- 5+ years in engineering leadership, including managing cross-functional or multi-stack teams.
- Hands-on experience in modern cloud environments, especially AWS (Fargate, Lambda, Serverless, Docker, CDK, CloudFormation).
- Fluency in at least one major backend language (Ruby, PHP, Python, etc.) and experience with web frameworks (Ruby on Rails, Laravel, Django, or Express).
- Strong technical breadth, comfortable overseeing both a Ruby-based API/backend team and a PHP/WordPress/LAMP product team.
- Proactive interest in AI technologies and curiosity to explore practical AI use cases.
- Knowledge of REST API design (jsonapi.org) and familiarity with front-end frameworks like React, Vue, or Angular.
- Proven ability to mentor developers across diverse disciplines (modern JavaScript, cloud infrastructure, LAMP stack, WordPress plugin development).
Bonus Points:
- Deep experience with Ruby on Rails and PostgreSQL.
- Experience with WordPress Gutenberg block editor, WooCommerce, and plugin development.
- Prior work with React/Redux and Node.js.
- Comfort working with BI/data tools like ElasticSearch, SQL, or Metabase.
- Experience building and scaling CI/CD pipelines using GitHub Actions, AWS CDK, or CloudFormation.
What Wicket Offers:
- The opportunity to work remotely from anywhere in Canada.
- Competitive salary and participation in the Employee Stock Option Plan.
- Competitive health benefits (dental, vision, paramedical, prescriptions, mental health support).
- Annual wellness stipend and dedicated professional development stipend/time.
- Great Place to Work™ certified culture, prioritizing diversity and inclusion.
- Paid vacation time, personal “life leave,” and your birthday off.