Director of Software Engineering

Loopio; Toronto; Hybrid; CAD 200,000 - 250,000; Full time

Job summary

A leading tech company in Canada seeks a Director of Software Development to lead their Library Mission Team, enhancing content retrieval and search capabilities. This role involves strategic leadership over multiple engineering pods, integrating cutting-edge technologies like ML and NLP. Ideal candidates have extensive experience in software development and a passion for fostering inclusive team environments. Offering flexible co-working locations in Ontario and a supportive, engaged workplace culture.

Benefits

Health and wellness benefits

MacBook laptop

Monthly phone and internet subsidy

Work-from-home budget

Qualifications

• 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.

Responsibilities

• Lead and grow multiple engineering pods including supporting other managers and technical leads.
• Drive the architecture and evolution of Loopio's content retrieval and hybrid search platform.
• Oversee planning, prioritization, and execution across multiple pods ensuring timely delivery.

Skills

Go

React

Node.js

GraphQL

Management Experience

Leadership Experience

Operations Management

Project Management

Research & Development

Software Development

Team Management

Education

Bachelor's or Master's degree in Computer Science or related field

Job description

Overview

Take your career to new heights with Loopio!

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.

What You’ll Be Doing

• 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.

What You Bring to the Team

• 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.
• Bachelors or Masters degree in Computer Science or related field, or equivalent industry experience.

Bonus Points

• 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 with HQ in Canada and established hub regions around the world. We hire from Canada, the UK, India, and other regions as appropriate. Our employees live and work in Canada (British Columbia and Ontario), London, and India (Gujarat, Maharashtra, Bengaluru). The majority of our team is based in Ontario and British Columbia.

We offer flexible co-working locations in Ontario and British Columbia. Those based in Ontario have access to a co-working space in Downtown Toronto; those in BC can work centrally in Vancouver. You’ll collaborate with teams virtually across the UK, India, and North America with core sync hours and focus time for heads-down work. We encourage asynchronous collaboration to effectively work as a global #OneTeam.

Why You’ll Be Working at Loopio

Your manager supports your development with ongoing feedback and regular 1-on-1s. We leverage Lattice for 1:1s and performance conversations.

You will have the opportunity to elevate your craft and receive a dedicated professional mastery allowance for learning support. We encourage experimentation and innovative thinking to drive business impact.

We offer a wide range of health and wellness benefits starting day 1, a MacBook laptop, a monthly phone and internet subsidy, and a work-from-home budget.

You’ll be joining a supportive culture with opportunities for connections in a remote-first environment, including town halls, AMA sessions, and quarterly celebrations as #oneteam.

We have Employee Resource Groups and an award-winning workplace, with the opportunity to make a big impact on the business.

We encourage applicants from all backgrounds and lifestyles. If you require accommodations at any point during our virtual interview processes, please contact a member of our Talent Experience team.

Required Experience

Director

Key Skills

Go, Lean, Management Experience, React, Node.js, Operations Management, Project Management, Research & Development, Software Development, Team Management, GraphQL, Leadership Experience

Employment Type : Full-Time

Experience : years

Vacancy : 1