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 teams Hold effective one-on-ones and provide timely, specific, actionable feedback Support engineers in building meaningful growth plans and developing their careers Recognize strong 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