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About the Role
Lead the engineering teams responsible for Checkfront and Regiondo, established booking-management products. Focus on stability, reliability, performance, and maintainability while delivering product improvements. Accountable for team health, development, performance, and delivery, working closely with Product and other leaders to set priorities and foster growth.
Responsibilities
- Set clear expectations and foster trust, accountability, and collaboration.
- Conduct effective one-on-ones and provide actionable feedback.
- Support engineers in career development and growth.
- Recognize strong performance and address concerns directly.
- Develop senior engineers and emerging technical leaders.
- Monitor team morale, workload, and capacity.
- Participate in hiring and onboarding.
- Partner with Product to establish priorities and delivery plans.
- Create alignment across teams with shared dependencies or competing priorities.
- Balance new development with reliability, maintenance, and technical health.
- Surface delivery risks, dependencies, and capacity constraints.
- Establish clear ownership and ensure accountability for quality delivery.
- Engage in production incidents and escalations.
- Maintain accountability for stable deployments and observability.
- Maintain technical and operational context for major systems and risks.
- Identify opportunities to improve team processes and engineering practices.
- Participate in technical discussions and help make pragmatic tradeoffs.
- Improve maintainability, observability, testing, reliability, and engineering quality.
- Ensure technical investments align with business outcomes.
- Understand practical constraints engineers face.
- Use evidence to assess the impact of changes to tools or practices.
Requirements
- Experience successfully leading and developing software engineers in a management role.
- Experience operating across multiple engineering teams and product areas.
- Strong people-management skills, including coaching, feedback, career development, expectation setting, and addressing performance concerns.
- Experience developing senior engineers or technical leaders.
- A track record of creating accountability without micromanagement.
- Strong operational instincts, including experience with production incidents, observability, reliability, and learning from failures.
- Strong written and verbal communication skills.
- Ability to communicate engineering concerns to Product, Support, leadership, and stakeholders.
- An ownership mindset: remain engaged until issues are resolved.
- Familiarity with PHP, React, PostgreSQL, and Google Cloud Platform is a plus.
- Experience working closely with customer-facing teams is a plus.
- Experience with AI-assisted software-development tools is a plus.
- Experience in booking, ecommerce, travel, tours and activities, or similar domains is a plus.
- Experience helping teams incrementally modernize complex systems is a plus.
- Experience improving test coverage, deployment automation, incident response, and production observability is a plus.
Skills
- People Management
- Coaching
- Feedback
- Career Development
- Expectation Setting
- Performance Management
- Technical Leadership
- Operational Acumen
- Production Incident Management
- Observability
- Reliability Engineering
- Communication (Written and Verbal)
- Stakeholder Management
- Ownership Mindset
- PHP
- React
- PostgreSQL
- Google Cloud Platform
- System Modernization
- Test Automation
- Deployment Automation
- Incident Response
Location
- Remote
Work Type
- Full-time
Experience Level
- Senior
Salary/Compensations
- $180,000–$220,000 CAD
About the Company
- Checkfront and Regiondo are established booking-management products used by thousands of tour, activity, and experience operators.
- Checkfront and Regiondo are mature, revenue-generating products with years of functionality and customer needs represented in their codebases.