Job Specifications
Job Title: Head of Software Engineering
Department: Engineering
Reports to: CEO
Term: Full-Time Permanent
Primary Location: Remote in Canada
Salary range: $130,000 – $150,000 CAD
Join Our Mission to Transform Association Technology!
At Wicket, we enable associations to thrive using a modern and flexible ecosystem of software. As a remote-first Canadian company, we're revolutionizing how associations operate and engage with their members through innovative technology solutions.
About Us
Wicket is pioneering the future of association technology with two groundbreaking products:
Wicket Member™: The world's first Member Data Platform (MDP), purpose-built to help associations break free from legacy systems and take control of their member data. This revolutionary platform creates a single source of truth for member information while enabling seamless integration with the tools associations use every day.
Wicket Web™: A powerful web and e-commerce platform built on WordPress and WooCommerce, specifically designed to meet associations' unique digital presence and online transaction needs.
Our diverse client base includes forward-thinking associations across North America who are making real-world impact - from organizations shaping public policy to those advancing healthcare standards. By choosing Wicket, you're not just joining a technology company; you're joining a mission to help associations realize their highest potential and create positive change in their communities.
Working at Wicket means being part of an innovative team that values thoughtful decision-making, proactive leadership, continuous learning, and collaborative success. If you're passionate about using technology to empower organizations that make a difference, we want to hear from you!
Learn more about our culture, values, and opportunities at wicket.io/careers
About You
We’re looking for a hands-on Head of Software Engineering to lead and grow our engineering team, set our technical vision, and partner with Product and Services to build great software our customers love.
Responsibilities of this role -
Technical Leadership
Own the technical direction and architecture across Wicket Member™ and Wicket Web™.
Ensure both 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 the latest advancements in AI/ML and identify opportunities for integration into Wicket’s offerings.
Collaborate with Product to prototype and implement AI-driven features that create real customer value.
Encourage a culture of learning and experimentation with AI tools and workflows within the software engineering team.
Hands-On Contribution
Contribute directly to the codebase for experimentation, especially on architecture-heavy or complex projects.
Review code and guide implementation decisions with an eye for long-term maintainability.
Help debug, unblock, and elevate the work of the software engineering team.
Team Leadership
Lead and support a growing team of developers across both products and software stacks.
Manage the technical customer support team, and establish processes to manage support requests alongside product work, customization requests, and support requests.
Mentor and develop software engineers and support staff through coaching, feedback, and growth planning.
Foster a collaborative and inclusive software engineering culture built on trust and autonomy.
Infrastructure & Tooling
Oversee our DevOps practices, CI/CD pipelines, and internal tooling for both our LAMP and API-first Rails Application and React Admin SPA stacks.
Ensure our systems are observable, secure, and easy to deploy and maintain.
Lead a push towards security and data privacy compliance, such as SOC2, SSDF, or ISO/IEC 27001.
Cross-Functional Collaboration
Partner closely with the Head of Product, who owns the product roadmap and Agile delivery process (sprint planning, estimation, retrospectives, etc.).
Collaborate closely with the Customer Implementation team to provide technical guidance, scope and understand custom software requests, and oversee prioritization.
Provide technical input into roadmap planning, product trade-offs, and feasibility.
Technical Knowledge and Requirements -
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).
Proactive interest in AI technologies - stays current with trends in AI and developer productivity tools. Curiosity to explore and adopt practical, impactful AI use cases both internally and to develop AI features within our products.
Fluency in at least one major backend language (Ruby, PHP, Python, etc.) and experien
About the Company
Wicket is a SaaS membership software that is built to integrate with best-in-class software such as MailChimp, Shopify, Eventbrite, and Drupal. It breaks down data silos, giving member-driven organizations flexibility to use the world’s best software by integerating and sharing data. We empower associations and member-based organizations to manage their data in a simple and effective way. No more inefficient and manual workarounds. No more data silos and random spreadsheets. Smarter, easier member management.
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