Senior Engineering Manager – Checkfront & Regiondo About the Role We’re looking for an Engineering Manager to lead the teams responsible for Checkfront and Regiondo, 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. The teams will continue delivering meaningful product improvements while placing increased emphasis on stability, reliability, performance, maintainability, and operational confidence.
As a Senior Engineering Manager, you will be accountable for the health, development, performance, and delivery of the engineering teams for both products. You’ll work closely with Product, senior technical contributors and other engineering leaders to establish priorities, make sound tradeoffs, and create an environment in which engineers can effectively work and grow.
We employ a player-coach model for engineering leadership. You won’t be expected to be the team’s primary implementer or sole technical decision maker, and your success will not be measured by your personal output. You will, however, be expected to remain close enough to the work to represent the major systems, architectural decisions, delivery risks, incidents, and operational characteristics across your area. You should be able to explain the technical approach for both teams, participate credibly in engineering discussions, and make high-level decisions.
This is a role for a technical leader who enjoys leading people as well as improving how engineering teams build and deliver quality software.
What You’ll Do Lead and Develop Teams Set clear expectations and create an environment of trust, accountability, and respectful collaboration across the Checkfront and Regiondo teams
Hold effective one-on-ones and provide timely, specific, actionable feedback
Support engineers in building meaningful growth plans and developing their careers
Recognize robust performance and address performance concerns directly
Develop senior engineers and emerging technical leaders,



creating opportunities for them to take on broader responsibilities
Maintain awareness of team morale, workload, delivery constraints, interpersonal dynamics, and capacity
Participate in hiring and onboarding new team members as the teams evolve
Own Multi-Team Delivery and Operational Outcomes Partner closely with Product to establish priorities, sequencing, and delivery plans across both products, aligning to the tech organization’s overall goals
Create alignment when teams have shared dependencies, competing priorities, or overlapping ownership
Balance new product development with reliability, maintenance, testing, technical debt, performance, and longer-term engineering health
Surface delivery risks, dependencies, ownership gaps and capacity constraints early
Establish clear ownership and hold teams accountable for delivering work to an appropriate quality standard
Remain actively engaged in production incidents and escalations, understanding their customer impact, contributing factors, and remediation
Maintain accountability for stable, secure deployments and appropriate post-deployment observability
Provide Technical and Operational Leadership Maintain sufficient technical and operational context across Checkfront and Regiondo to understand their major systems, dependencies, risks, and incidents
Identify opportunities to make team processes and engineering practices more effective
Participate in important technical discussions, challenge assumptions, and help the team make pragmatic tradeoffs
Help the teams improve maintainability, observability, testing, reliability, and overall engineering quality
Ensure that technical investments are connected to meaningful customer, product, operational, or business outcomes




Stay hands‑on enough with both team’s work and systems to understand the practical constraints the engineers are working within
Use evidence to understand whether changes to tools or working practices are actually improving team outcomes
What We’re Looking For Experience successfully leading and developing software engineers in an Engineering Manager, Senior Engineering Manager, or comparable engineering leadership 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 relying on micromanagement
Strong operational instincts, including experience with production incidents, observability, reliability, and learning from recurring failures
Strong written and verbal communication skills, and the ability to communicate engineering concerns to Product, Support, leadership, and other stakeholders
An ownership mindset: when something affecting your area is going wrong, you stay engaged until there is clarity around impact, ownership, next steps, and resolution
Nice to Have Familiarity with some of the technologies used across Checkfront and Regiondo, including PHP, React, PostgreSQL, and Google Cloud Platform
Experience working closely with customer-facing teams such as Support or Customer Success
Experience with AI‑assisted software‑development tools and an interest in applying them pragmatically and responsibly
Experience in booking, ecommerce, travel, tours and activities, or other operationally complex domains
Experience helping teams incrementally modernize complex systems without requiring large‑scale rewrites
Experience improving test coverage, deployment automation, incident response, and production observability
The salary range for this role is $180,000–$220,000 CAD depending on the candidate’s skillset, experience, and overall qualifications.

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📌 Senior Engineering Manager (Ontario)
🏢 Checkfront
📍 Ontario