Senior Engineering Manager

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 teamsHold effective one-on-ones and provide timely, specific, actionable feedbackSupport engineers in building meaningful growth plans and developing their careersRecognize strong performance and address performance concerns directlyDevelop senior engineers and emerging technical leaders, creating opportunities for them to take on broader responsibilitiesMaintain awareness of team morale, workload, delivery constraints, interpersonal dynamics, and capacityParticipate in hiring and onboarding new team members as the teams evolveOwn 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 goalsCreate alignment when teams have shared dependencies, competing priorities, or overlapping ownershipBalance new product development with reliability, maintenance, testing, technical debt, performance, and longer-term engineering healthSurface delivery risks, dependencies, ownership gaps and capacity constraints earlyEstablish clear ownership and hold teams accountable for delivering work to an appropriate quality standardRemain actively engaged in production incidents and escalations, understanding their customer impact, contributing factors, and remediationMaintain accountability for stable, secure deployments and appropriate post-deployment observabilityProvide Technical and Operational Leadership
Maintain sufficient technical and operational context across Checkfront and Regiondo to understand their major systems, dependencies, risks, and incidentsIdentify opportunities to make team processes and engineering practices more effectiveParticipate in important technical discussions, challenge assumptions, and help the team make pragmatic tradeoffsHelp the teams improve maintainability, observability, testing, reliability, and overall engineering qualityEnsure that technical investments are connected to meaningful customer, product, operational, or business outcomesStay hands‑on enough with both team’s work and systems to understand the practical constraints the engineers are working withinUse evidence to understand whether changes to tools or working practices are actually improving team outcomesWhat We’re Looking For
Experience successfully leading and developing software engineers in an Engineering Manager, Senior Engineering Manager, or comparable engineering leadership roleExperience operating across multiple engineering teams and product areasStrong people-management skills, including coaching, feedback, career development, expectation setting, and addressing performance concernsExperience developing senior engineers or technical leadersA track record of creating accountability without relying on micromanagementStrong operational instincts, including experience with production incidents, observability, reliability, and learning from recurring failuresStrong written and verbal communication skills, and the ability to communicate engineering concerns to Product, Support, leadership, and other stakeholdersAn ownership mindset: when something affecting your area is going wrong, you stay engaged until there is clarity around impact, ownership, next steps, and resolutionNice to Have
Familiarity with some of the technologies used across Checkfront and Regiondo, including PHP, React, PostgreSQL, and Google Cloud PlatformExperience working closely with customer-facing teams such as Support or Customer SuccessExperience with AI‑assisted software‑development tools and an interest in applying them pragmatically and responsiblyExperience in booking, ecommerce, travel, tours and activities, or other operationally complex domainsExperience helping teams incrementally modernize complex systems without requiring large‑scale rewritesExperience improving test coverage, deployment automation, incident response, and production observabilityThe 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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