Lead Software Engineer Technical Lead

About Us:

At OBASA & MyKey we love to delight our customers. OBASA Suites provides beautifully furnished suites for professionals and families in some of the most desirable buildings in Canada while MyKey helps insurance displaced families in the US & Canada find comfort after tragedy hits through fires floods and natural disasters.

Our CEO is dedicated to onboarding only the most qualified and experienced professionals to join our corporate family as we believe our team deserves exceptional leadership and support. If you are passionate about making a meaningful impact and possess the expertise we seek we look forward to connecting with you.

Career Description:

We are seeking an experienced Lead Software Engineer to lead the development architecture and operational excellence of our accommodation management platform. This is a hands-on leadership role for someone who can balance engineering execution architecture ownership infrastructure reliability and mentorship.

The ideal candidate has strong backendexpertise modern frontend experience and practical cloud infrastructure knowledge with the ability to scale systems in a fast-moving business environment.

Lead Software Engineer / Technical Lead

Tech Stack:Ruby on Rails React TypeScript AWS ECS

About the Role

We are seeking an experienced Lead Software Engineer to lead the development architecture and operational excellence of our accommodation management platform. This is a hands-on leadership role for someone who can balance engineering execution architecture ownership infrastructure reliability and mentorship.

The ideal candidate has strong backendexpertise modern frontend experience and practical cloud infrastructure knowledge with the ability to scale systems in a fast-moving business environment.

Key Responsibilities

Software Engineering & Architecture

Lead the architecture design and implementation of core platform systems and customer-facing applications.

Build andmaintainscalable backend services usingRuby on Rails.

Drive development initiatives using React and TypeScript.

Design clean maintainable APIs and integration layers for internal and external systems.

Lead modernization efforts system refactoring and technical debt reduction initiatives.

Establish engineering best practices coding standards and architectural guidelines.

Cloud Infrastructure & DevOps

Own application infrastructure deployed onAWS ECS.

Manage and improve CI/CD pipelines for reliable automated deployments.

Support containerized workloads and deployment strategies across environments.

Improve system observability logging monitoring and incident response processes.

Optimizecloud infrastructure for performance reliability and cost efficiency.

Collaborate on infrastructure automation and deploymenttoolingimprovements.

Scalability Performance & Reliability

Diagnose and resolve production performance bottlenecks and system issues.

Improve backend application performance database efficiency and service reliability.

Design systems capable of supporting business growth and increasing operational demand.

Lead incident investigations root cause analysis and preventative improvements.

Team Leadership & Collaboration

Mentor engineers through architecture guidance code reviews and technical coaching.

Partner with product operations support and leadership teams to deliver business-critical features.

Break down technical initiatives into executable workstreams.

Balance short-term delivery needs with long-term platform sustainability.

Platform Integrations

Build andmaintainintegrations with third-party vendors partner platforms and business systems.

Support API integrations related to bookings accommodations payments partner workflows and operational systems.

Operational Ownership

Participate in production support and critical issue resolution.

Improve release management deployment processes andengineering operational maturity.

Maintain documentation technical runbooks and architectural knowledge sharing.

Required Qualifications

8 years of professional software engineering experience.

Strong production experience withRuby on Rails.

Strong frontend experience withReact and TypeScript.

Proven experience deploying and operating applications onAWS ECS.

Strong CI/CD experience (GitLab CI or similar).

Solid experience with containerization and Docker workflows.

Strong database experience (PostgreSQL/MySQL).

Experience troubleshooting production systems and performance issues.

Experience leading technical projects and mentoring engineers.

Strong communicationand cross-functional collaboration skills.

Nice to Have

Experience in hospitality accommodation insurance housing or booking platforms.

Experience integrating third-party APIs and partner systems.

Experience improving observability and operational tooling.

Exposure to infrastructure as code (Pulumi)

Success Metrics

Improved platform stability and uptime.

Faster safer deployment cycles.

Reduced production incidents and faster issue resolution.

Improved engineering velocity and code quality.

Successful delivery of key platform initiatives.

Better system scalability and operational readiness.