Vice President of Engineering

New
C
CheckmateRestaurant technology
United StatesFull-TimeVp
Salary not disclosed
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Job Details

Experience
12+ years of progressive software engineering experience, with 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. 7+ years hands-on experience with asynchronous processing and architectures. 5+ years working in and managing a 100% remote based team.
Required Skills
AWSAgileRuby on RailsCI/CDMicroservices

Requirements

  • Have 12+ years of progressive software engineering experience.
  • Have 5+ years in senior engineering leadership roles managing engineering managers and cross-functional teams.
  • Have 7+ years of hands-on experience with asynchronous processing and architectures.
  • Have 5+ years of experience working in and managing a 100% remote team.
  • Bring SaaS or web-based startup experience in fast-paced, high-growth environments.
  • Have experience leading globally distributed engineering teams and cross-cultural team management.
  • Have experience building and scaling applications hosted on AWS.
  • Have experience driving engineering teams to adopt AI-driven development practices, such as Claude Code.
  • Have a foundation in modern full-stack web architectures, databases, API design, microservices, and web protocols including REST, JSON, OAuth, and SSL.
  • Be able to collaborate with peer engineering leaders and senior stakeholders under executive direction.
  • Be adaptable and able to manage multiple time-constrained priorities with minimal guidance.
  • Ruby on Rails ecosystem, performance tuning, or Rails application scaling experience is a strong plus.

Responsibilities

  • Lead, mentor, and grow globally distributed software engineering teams, including development teams based in India.
  • Drive architectural vision and technical design for the product domain, including scalable, secure, cost-efficient AWS deployments.
  • Champion engineering practices for design standards, code reusability, automated testing, system performance, and technical debt remediation.
  • Partner with platform and infrastructure leaders to integrate software designs with CI/CD pipelines and cloud infrastructure.
  • Own the engineering operating model, including sprint and release cadence, planning, code review, deployment practices, and definition-of-done criteria.
  • Define, measure, and report on delivery, quality, predictability, and team-health metrics.
  • Run retrospectives, post-incident reviews, and process assessments, and turn findings into owned improvement initiatives.
  • Measure and refine the impact and adoption of AI-assisted development tools and workflows.
  • Partner with Product Management, Data Analytics, and Customer Success to align technical roadmaps with business objectives and releases.
  • Collaborate with peer engineering VPs and manage strategic software vendor and third-party partner relationships.
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