Jobs in Ajax, Canada

Loopio is a workplace that unleashes learning and growth opportunities for our Loopers. We provide autonomous, challenging work that allows each employee to master their craft. We attract and retain people who are naturally curious, have grit, and are eager to grow their careers. At Loopio, we genuinely support each other—because true success comes from working as #oneteam.

We’re looking for a Director of Software Development to lead our Library Mission Team, which is responsible for the content retrieval systems that power the core of the Loopio platform. This includes our hybrid search capabilities, OpenSearch infrastructure, and emerging investments in natural language search, semantic indexing, and ML-enhanced content retrieval.

This is a strategic and technical leadership role ideal for someone with deep expertise in content discovery and retrieval systems, experience with natural language and search ranking models, and the ability to manage multiple pods—including other engineering managers. You’ll work closely with leaders across Product, Data Science, Infrastructure, and Design to deliver scalable, intelligent systems that enhance how our customers access and organize content.

• Leadership & Team Development

  • Lead and grow multiple engineering pods, including supporting other managers and technical leads.
    

  • Foster a high-performing, inclusive engineering culture centered on accountability, autonomy, and craft.
    

  • Mentor and develop engineering leaders, helping them grow through coaching and clear feedback.
    

  • Attract, retain, and nurture top technical talent across Canada, India, and the UK.
    

• Technical Direction & Architecture

  • Drive the architecture and evolution of Loopio’s content retrieval and hybrid search platform.
    

  • Partner with Data and ML teams to integrate semantic search, ranking models, and NLP-enhanced retrieval.
    

  • Make technical decisions that balance short-term velocity with long-term scalability and maintainability.
    

  • Provide hands-on architectural guidance, ensuring strong design patterns and system reliability.
    

• Execution & Delivery

  • Oversee planning, prioritization, and execution across multiple pods, ensuring timely delivery and alignment to roadmap goals.
    

  • Collaborate with Product and Design partners to translate customer needs into intelligent, performant features.
    

  • Proactively manage technical dependencies, risks, and cross-team coordination.
    

• Operational Excellence

  • Champion high-quality engineering practices, observability, testing, and performance optimization.
    

  • Lead incident response and root cause analysis for content retrieval systems.
    

  • Continuously refine workflows, tooling, and delivery processes for team efficiency.
    

• Cross-Functional Collaboration

  • Serve as a key voice in strategic planning and technical vision for Library-related initiatives.
    

  • Collaborate with Data, Infrastructure, and Platform teams on scalable solutions for data ingestion, indexing, and retrieval.
    

  • Effectively communicate technical decisions to stakeholders across the business.
    

• Innovation & Emerging Technologies

  • Explore and implement ML techniques to improve search quality, semantic understanding, and ranking.
    

  • Keep up with trends in search infrastructure (e.g., OpenSearch/Elasticsearch), vector databases, LLM integration, and AI-enhanced UX.
    

  • Encourage innovation and experimentation in how users interact with large content libraries.

• 10+ years of experience in software development, including 3–5+ years in engineering leadership roles.
  

• Proven success in managing and scaling multiple engineering pods and/or other managers.
  

• Deep experience in search infrastructure, information retrieval, or ML/NLP applications.
  

• Technical fluency in building and optimizing large-scale distributed systems.
  

• Familiarity with semantic search, vector embeddings, hybrid search strategies, or LLM-enhanced search.
  

• Excellent communication skills, with the ability to align technical initiatives with business outcomes.
  

• Track record of fostering inclusive, high-trust team environments.
  

• Bachelor’s or Master’s degree in Computer Science or related field—or equivalent industry experience.

• Bonus Points For:

  • Experience with OpenSearch or Elasticsearch internals (sharding, relevancy tuning, ingest pipelines).
    

  • Background in ML/AI pipelines or ranking models for search.
    

  • Experience with SaaS platforms, especially multi-tenant architectures.

Where You’ll Work

• Loopio is a remote-first workplace because we recognize the advantages of working flexibly. We are HQ’d in Canada, with established hub regions around the world where we hire from.

• Our employees (or Loopers, as we call ourselves!) live and work in Canada (British Columbia and Ontario), London, and India (specifically in Gujarat, Maharashtra, and Bengaluru).

• The majority of our team is based in ON and BC, which means these employees live and work remotely within a 300km radius of Toronto (within Ontario) and Vancouver (Within BC).

• We offer flexible co-working locations available to Loopers in ON and BC. Those based in ON have the option of working out of our convenient co-working space located in the heart of Downtown Toronto and a 12-minute walk from Union Station. BC Loopers have the option to work centrally in Vancouver. It is whatever works best for you!

• You’ll collaborate with your teams virtually across the UK, India, and North America (we’re just a Zoom call and Slack message away!) with core sync hours and focus time for headsdown work during the workday

• We encourage asynchronous collaboration to effectively work as a global #OneTeam!

Why You’ll ️ Working at Loopio

• Your manager supports your development by providing ongoing feedback and regular 1-on-1s, we leverage Lattice for our 1:1s and performance conversations

• You will have the opportunity to elevate ???? your craft and the opportunity to explore your creativity, with a dedicated professional mastery allowance for more learning support! We encourage experimentation and innovative thinking to drive business impact.

• We offer a wide range of health and wellness benefits to support your physical and mental well-being, starting day with Loopio.

• We’ll set you up to work remotely with a MacBook laptop , a monthly phone and internet subsidy, and a work-from-home budget to help get your home office all set up.

• You’ll be joining a supportive culture that has thoughtfully built out opportunities for connections in a remote first environment.

• Participate in townhalls, AMA (Ask-Me-Anything), and quarterly celebrations to celebrate the big wins and milestones as #oneteam!

• Our four active Employee Resource Groups offer opportunities for employees to learn and connect year-round.

• You’ll be a part of an award-winning workplace with an opportunity to make a big impact on the business.

Questioning your qualifications? Read this ️ Hi there, we recognize that all too often, potential candidates don’t apply for a position simply because they don’t hit every single criteria included in the job description—particularly members of underrepresented groups.

Whether or not your experience checks off all the boxes on a job posting, we still encourage you to apply to ensure that your application receives a review from our team. We understand that a resume can only showcase so much during the applicant stage, so we've created prompts in the application for you to share more about yourself. If you've made a career transition (or a few!), you’re self taught in a new role, or you have skills/experience you’d like to highlight, we want to hear more about what you could bring to the table.

AI in Recruitment At Loopio, we leverage artificial intelligence (AI) technology to enhance our recruitment process. These tools assist with tasks such as resume screening, drafting preliminary job descriptions, generating initial interview questions, and occasionally sourcing prospective candidates. However, AI is never used to make final hiring decisions; our use of AI serves to support repetitive and administrative tasks in order to streamline our hiring and recruitment workflows. We are committed to the responsible use of AI in our hiring practices, prioritizing both an improved candidate experience and operational efficiency. Our standardized hiring practices remain focused on reducing biases, with all key hiring decisions solely made by our team. We continuously review and refine our hiring practices to align with industry best practices and evolving legal guidelines

Loopio is an equal opportunity employer that is deeply committed to building equitable workplaces that are diverse and inclusive. We actively encourage candidates from all backgrounds and lifestyles to consider us as a future employer. Please contact a member of our Talent Experience team (work@loopio.com) should you require accommodations at any point during our virtual interview processes.