Head of Software Engineering

Get AI-powered advice on this job and more exclusive features. Direct message the job poster from Wicket Inc. 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 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. 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. 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 experience with web frameworks like 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. Knowledge of REST API design (we use jsonapi.org) and familiarity with front‑end frameworks like React, Vue, or Angular. Excellent communication skills and the ability to translate between technical and non‑technical stakeholders. A collaborative leader who creates clarity, supports autonomy, and drives technical excellence. Bonus Points For Deep experience with Ruby on Rails and PostgreSQL. Experience withPress Gutenberg block editor, WooCommerce, and plugin development. Prior work with React/Redux, Node.js, and frontend component‑based architecture. Comfort working with BI/data tools like ElasticSearch, SQL, or Metabase. Experience building and scaling CI/CD pipelines, especially using GitHub Actions, AWS CDK, or CloudFormation. Experience working with Agile methodologies, writing user stories, or technical specs. A background in computer science, engineering, or a recognized software/web development program. Desired Soft Skills Empathetic leadership – You create psychological safety, lead with humility, and genuinely care about your team’s growth and well‑being. Clear communication – You can explain complex technical decisions to non‑technical stakeholders and keep your team aligned without ambiguity. Collaborative mindset – You see Product, Engineering, and Services as partners in a shared mission, not silos. Decisiveness with curiosity – You’re comfortable making tough calls, but you ask great questions first and welcome input. Bias for action – You unblock others, simplify where possible, and balance pragmatism with long‑term thinking. Mentorship orientation – You take pride in helping others level up and creating a culture of learning, ownership, and autonomy. Adaptability – You thrive in a dynamic environment and enjoy evolving processes, tools, and teams to meet changing needs. What We Offer The opportunity to work remotely from anywhere in Canada Participation in the Employee Stock Option Plan Competitive health benefits (dental, vision, paramedical, prescriptions, out‑of‑country care) that extend to programs including mental health and employee family assistance An annual wellness stipend towards gym memberships, fitness equipment, sports fees, etc. An annual professional development stipend and dedicated time for professional development Highly intentional, progressive practices around feedback, team‑building, skills and career development, and peer‑to‑peer recognition An equal opportunity employer who prioritizes diversity and inclusion Awesome culture and a growing team that has been around for over 20 years Paid vacation time, personal “life leave” and your birthday off We love dogs, trivia, and wine/beers/soda on Friday We are accepting applications for remote workers from anywhere in Canada. When you apply please provide a cover letter clearly explaining how your background is a good fit for this position. Wicket is committed to creating a diverse environment and is proud to be an equal‑opportunity employer. All qualified applicants will receive consideration for employment without regard to race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, or age. #J-18808-Ljbffr