At Checkfront, we're builders, doers, and difference-makers, driven by a shared mission to reshape the tours, activities, and experiences industry. Alongside our sister brands, Rezdy and Regiondo, we power more than 20,000 businesses and support over $10B in bookings globally. Our technology helps operators thrive while delivering unforgettable moments to travelers around the world.
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
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
- 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
Skills Required
- Significant experience as a senior or staff-level software engineer on product-focused teams
- Comfortable working in large, mature, or complex codebases
- Ability to lead on maintenance, reliability, performance, and product development work
- Experience partnering with product and customer-facing teams to shape requirements and technical plans
- Mentor other engineers via guidance, pairing, code review, and design discussions
- Strong focus on reliability, performance, testability, observability, and operational quality
- Ability to identify and incrementally reduce technical debt without disrupting product delivery
- Can use AI-assisted development tools thoughtfully while maintaining strong engineering judgement
- Strong PHP experience in production environments
- Experience with React, Postgres, cloud infrastructure, CI/CD pipelines, and observability tooling
- Experience in booking, ecommerce, travel, tours and activities or other operationally complex domains
What We Do
Checkfront helps schedule-based businesses better manage their operations, centralize administration, and sell and market their services online. Our cloud-based booking application provides a centralized business management tool while offering self-service bookings from a merchant's own website. We find innovative ways to ensure awareness and occupancy of your venues, activities and special events. Make it easy for your customers to find, select, and book your services. Checkfront combines leading technologies and industry best practices to ensure customer satisfaction.
