Staff Software Engineer

About the Role

We’re looking for a Staff Software Engineer to join the Checkfront team. Checkfront is an established SaaS platform in the tours and activities industry with real customers and meaningful scale. The team is focused on maintaining and improving the product with work spanning reliability, performance, retention, maintainability, and new feature development.

As a Staff Engineer, you’ll work closely with engineering, product, and customer-facing teams to help the team deliver well-scoped, high-quality work while improving the health and stability of the platform over time.

We’re looking for an experienced, product-focused engineer who can raise the technical bar, identify the right seams for improvement, reduce risk, and help the team move faster with confidence.

What You’ll Do

• Provide technical leadership on maintenance, reliability, performance, and product development work
• Partner with Product to understand requirements, clarify technical constraints, and shape implementation plans
• Collaborate with stakeholders to understand customer pain points, production issues, and operational risks
• Improve delivery quality through better patterns, thoughtful code review, clearer technical plans, and stronger rollout practices
• Identify opportunities to improve testability, observability, reliability, and maintainability
• Help the team reduce technical debt incrementally without disrupting ongoing product delivery
• Mentor other engineers through technical guidance, pairing, code review, and design discussions
• Contribute to process improvements that help the team plan, deliver, and operate more effectively over time

What We’re Looking For

You may be a fit for this role if you:

• Have significant experience as a senior or staff-level software engineer on product-focused teams
• Are comfortable working in large, mature, or complex codebases
• Know how to make incremental improvements that reduce risk and improve maintainability over time
• Can balance customer needs, business priorities, technical debt, and delivery risk
• Care deeply about reliability, performance, testability, and operational quality
• Can create technical clarity from complex systems, unclear boundaries, and imperfect abstractions
• Communicate clearly and directly with engineers, product managers, support teams, and other stakeholders
• Can use AI-assisted development tools thoughtfully and effectively while maintaining strong engineering judgement 
• Can help improve team process without being dogmatic about methodology
• Lead through influence, example, and technical credibility rather than authority
• Enjoy mentoring other engineers and helping a team raise its overall level of execution
• Are pragmatic, steady, and thoughtful when working on business-critical systems

Nice to Have

• Experience in booking, ecommerce, travel, tours and activities, or other operationally complex domains
• Experience modernizing older systems incrementally while continuing to ship customer-facing work
• Strong PHP experience in production environments
• Strong experience with React, Postgres, cloud infrastructure, CI/CD pipelines, and observability tooling
• Experience improving test coverage, deployment confidence, incident response, or production diagnostics