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 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 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