ItsaCheckmate builds digital ordering technology for restaurants, bringing web, app, kiosk, and third-party orders into a connected platform. The company’s tools include loyalty programs, catering management, QR-code ordering, and channel management, helping restaurant teams coordinate orders, reduce errors, and support day-to-day operations. ItsaCheckmate serves more than 2,400 brands and offers a marketplace of integrations.
Vice President of Engineering
Lead globally distributed engineering teams building AWS-based ordering and AI solutions. Set technical direction, strengthen engineering practices, and scale software for restaurant brands.
Description
- Lead and develop distributed engineering teams across regions, including India.
- Build an inclusive, high-performing culture through clear communication and coordinated execution across time zones.
- Adopt AI development tools and workflows, including coding assistants, automated test generation, and AI-supported code reviews.
- Recruit and retain talent, create career paths, and coach engineering managers and technical leads.
- Set product architecture and technical direction for scalable, secure, cost-efficient AWS deployments.
- Promote engineering standards for design, reusable code, automated testing, performance, and technical debt.
- Coordinate with platform and infrastructure leaders to connect software design with company CI/CD pipelines and cloud infrastructure.
- Own the engineering operating model, covering sprint and release schedules, planning, estimation, code reviews, branching, deployments, and completion criteria.
- Create scalable ways of working for a remote, globally distributed team.
- Define and report metrics for delivery, quality, predictability, and team health.
- Lead retrospectives, incident reviews, and quarterly process assessments, turning findings into measurable improvements.
- Evaluate AI-assisted development tools for effects on speed, quality, and developer experience, and adjust adoption practices.
- Balance feature work, technical debt, and operational needs through capacity planning and roadmap discussions with Product.
- Align technical roadmaps with business goals, user experience, and releases in partnership with Product Management, Data Analytics, and Customer Success.
- Set shared engineering standards, frameworks, and cross-team practices with fellow engineering VPs reporting to the CTO.
- Manage strategic software vendors and third-party partnerships.
- Refine Agile practices to improve delivery speed and product quality.
Requirements
- Bring 12 or more years of progressive software engineering experience, including at least five years in senior leadership managing engineering managers and cross-functional teams.
- Seven or more years of hands-on experience with Ruby on Rails patterns, performance tuning, or scaling legacy and modern Rails applications is a strong plus.
- Have at least seven years of hands-on experience with asynchronous processing and architectures.
- Have at least five years of experience working on and managing fully remote teams.
- Show success in SaaS or web startup settings, thriving in fast-growing environments that demand speed and adaptability.
- Demonstrate experience leading engineers across countries and managing cross-cultural teams.
- Collaborate effectively with peer engineering leaders and senior stakeholders under executive direction.
- Show proven expertise building and scaling applications on AWS.
- Have implemented AI-driven development practices, such as Claude Code, to improve team workflows and output.
- Bring a strong grounding in modern full-stack web architecture, databases, API design, microservices, and web protocols including REST, JSON, OAuth, and SSL.
- Adapt readily and manage multiple urgent priorities with minimal guidance.