[Hiring] Vice President of Engineering @Checkmate

Role Description

As a Vice President of Engineering, you will operate as a player/coach and join a collaborative team of VPs of Engineering reporting directly to the Chief Technology Officer (CTO). In this role, you will lead globally distributed software engineering teams driving the execution, architectural integrity, and delivery of core product initiatives built on cloud-native architectures in AWS.

Drawing on your experience in high-growth SaaS and web-based startup environments, you will serve as a key technical leader across the organization, partnering closely with Product leadership, Data Analytics, and cross-functional teams to build high-performance, scalable software that drives business growth. You will also be at the forefront of modern engineering management, actively driving teams to adopt AI-driven development practices to increase velocity, code quality, and developer productivity.

Essential Job Functions

• Global Engineering Leadership & Talent
  • Lead, mentor, and grow distributed software engineering teams located across global regions, with direct leadership experience overseeing development teams based in India.
  • Foster a high-performance, inclusive culture that excels across time zones, ensuring clear communication, alignment, and operational execution.
  • Champion and integrate modern AI-driven development tools and workflows (e.g., AI coding assistants, automated test generation, AI-assisted code reviews) to accelerate execution and upskill engineering talent.
  • Recruit, develop, and retain top talent, establishing clear career progression pathways and coaching engineering managers and technical leads.
• Technical Strategy & Architectural Excellence
  • Drive architectural vision and technical design for your product domain, ensuring scalable, secure, and cost-efficient deployments natively on AWS.
  • Champion modern engineering best practices, including design standards, code reusability, automated testing, system performance, and technical debt remediation.
  • Partner with platform and infrastructure leaders to ensure software designs integrate smoothly into company-wide CI/CD pipelines and cloud infrastructure.
• Process Development, Continuous Improvement & Team Metrics
  • Design, document, and own the engineering operating model for a team of engineers, including sprint and release cadence, planning and estimation, code review standards, branching and deployment practices, and definition-of-done criteria.
  • Establish lightweight, scalable processes that fit a remote, globally distributed team.
  • Define, instrument, and report on team performance metrics covering delivery, quality, predictability, and team health.
  • Run a regular continuous improvement cycle, including retrospectives, post-incident reviews, and quarterly process assessments.
  • Measure the impact of AI-assisted development tools on velocity, quality, and developer experience.
  • Maintain a sustainable balance between feature delivery, technical debt remediation, and operational work.
• Cross-Functional Collaboration & Process
  • Work closely with Product Management, Data Analytics, and Customer Success teams to align technical roadmaps with business objectives.
  • Collaborate with peer VPs of Engineering under the CTO to establish consistent engineering standards and cross-team processes.
  • Manage strategic software vendor and third-party partner relationships to scale capability in a fast-moving SaaS environment.
  • Implement and continuously refine Agile processes to reduce friction, increase delivery velocity, and elevate product quality.

Qualifications

• 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.
• Proven SaaS / web-based startup experience, with a track record of thriving in fast-paced, high-growth environments.
• Demonstrated experience leading engineering team members globally with deep familiarity in cross-cultural team management.
• Strong track record of collaborating with peer engineering leaders and senior stakeholders under executive direction.
• Strong, proven expertise in building and scaling applications hosted on AWS.
• Experience actively implementing and driving engineering teams to adopt AI-driven development practices.
• Deep foundation in modern full-stack web architectures, databases, API design, microservices, and core web protocols (REST, JSON, OAuth, SSL).
• Highly adaptable and skilled at managing multiple time-constrained priorities simultaneously with minimal guidance.