VP of Engineering: AI-Driven SaaS & Global Teams

Checkmate; United States; Remote; USD 180,000 - 240,000; Full time

Job summary

Checkmate, a restaurant technology solution provider, is seeking a Vice President of Engineering to lead globally distributed software teams building cloud-native SaaS on AWS.

You will partner with Product, Data Analytics, and Customer Success to set technical strategy, drive AI-enabled development, and maintain high velocity while ensuring quality.

This role requires 12+ years in software engineering, 5+ years in senior leadership, and a proven track record managing remote teams.

Qualifications

• 12+ years of progressive software engineering experience.
• 5+ years in senior engineering leadership roles managing engineering managers and cross-functional teams.
• 7+ years hands-on experience with Ruby on Rails ecosystem patterns, performance tuning, or legacy/modern Rails application scaling is a strong plus.
• 5+ years working in and managing a 100% remote based team.

Responsibilities

• Lead, mentor, and grow distributed software engineering teams located across global regions.
• Drive architectural vision and technical design for product domains on AWS.
• Partner with Product, Data Analytics, and Customer Success to align roadmaps with business goals.
• Implement Agile processes to reduce friction and increase delivery velocity.
• Measure team performance and drive continuous improvement initiatives.

Skills

Ruby on Rails

AWS

Remote team leadership

AI tooling

Software architecture

Cross-functional collaboration

Tools

Claude Code

CI/CD tooling

AWS CloudFormation

Job description

Checkmate, a restaurant technology solution provider, is seeking a Vice President of Engineering to lead globally distributed software teams building cloud-native SaaS on AWS.

You will partner with Product, Data Analytics, and Customer Success to set technical strategy, drive AI-enabled development, and maintain high velocity while ensuring quality.

This role requires 12+ years in software engineering, 5+ years in senior leadership, and a proven track record managing remote teams.