Teams at Checkmate (itsacheckmate.com)

Leads Checkmate’s global post-sale operations organization across onboarding, menu management, and technical account management. Owns service strategy, customer satisfaction, operational metrics, enterprise escalations, onboarding outcomes, process standardization, and team performance. Partners with Sales, Product, and Engineering to resolve systemic issues, improve product capabilities, reduce churn, and scale workflows through automation and AI-driven analytics. Acts as a strategic operational partner to the CEO.

Build, operate, and scale enterprise web applications using Python and React.js. Develop REST and GraphQL APIs, asynchronous processing, responsive interfaces, database queries, automated tests, and CI/CD workflows. Own features end to end, improve architecture and observability, modernize legacy systems, resolve outages, reduce technical debt, and mentor engineers. Collaborate with Product and Design in a remote, pod-based organization while leveraging AI coding agents.

Leads globally distributed software engineering teams, setting technical strategy, architecture, delivery processes, and engineering standards for AWS-based SaaS products. Partners with Product, Data Analytics, and Customer Success, develops engineering talent, manages vendors, drives continuous improvement, and promotes AI-assisted development practices. The role requires extensive software engineering and executive leadership experience, Ruby on Rails and asynchronous architecture expertise, AWS scalability knowledge, and experience managing remote global teams.