Vice President of Engineering

ItsaCheckmate

. Lead, mentor, and grow distributed software engineering teams across global regions, including teams based in India .

Posted 10/14/2026full-timeRemote • United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in leading and mentoring distributed software engineering teams, with a strong focus on AI-driven development practices and AWS architecture. Proven ability to foster a high-performance culture while managing cross-functional teams in a remote environment.

Highest-signal resume keywords

AWS ArchitectureRuby On RailsAI-Driven Development PracticesAgile MethodologiesCross-Cultural Team Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Software EngineeringAsynchronous ProcessingFull-Stack Web ArchitecturesAPI DesignMicroservicesPerformance TuningAutomated TestingTechnical DesignCode Review StandardsSaaS Development

Soft Skills

LeadershipCollaborationCommunicationAdaptabilityMentoring

Tools & Technologies

CI/CD PipelinesCloud InfrastructureAI Coding AssistantsAutomated Test GenerationTechnical Debt Remediation

Industry Keywords

Remote Team ManagementHigh-Growth EnvironmentsEngineering Best PracticesGlobal Team LeadershipProduct Management Alignment

Tech Stack

Tools & technologies

AWSCloudMicroservicesRubyRuby on Rails

About the role

Key responsibilities & impact

Lead, mentor, and grow distributed software engineering teams across global regions, including teams based in India
Foster a high-performance, inclusive culture across time zones with clear communication, alignment, and operational execution
Champion and integrate AI-driven development tools and workflows, including AI coding assistants, automated test generation, and AI-assisted code reviews
Recruit, develop, and retain engineering talent; establish career progression pathways and coach engineering managers and technical leads
Drive architectural vision and technical design for the product domain, ensuring scalable, secure, and cost-efficient AWS deployments
Champion engineering best practices covering design standards, code reusability, automated testing, system performance, and technical debt remediation
Partner with platform and infrastructure leaders to integrate software designs with company-wide CI/CD pipelines and cloud infrastructure
Design, document, and own the engineering operating model, including sprint and release cadence, planning and estimation, code review standards, branching and deployment practices, and definition-of-done criteria
Establish scalable processes for a remote, globally distributed team
Define, instrument, and report delivery, quality, predictability, and team-health metrics
Run retrospectives, post-incident reviews, and quarterly process assessments; convert findings into measurable improvement initiatives
Measure the impact of AI-assisted development tools on velocity, quality, and developer experience, refining adoption practices accordingly
Balance feature delivery, technical debt remediation, and operational work through capacity allocation and roadmap trade-off discussions with Product
Align technical roadmaps with business objectives, user experience goals, and feature releases alongside Product Management, Data Analytics, and Customer Success
Establish consistent engineering standards, shared technical frameworks, and cross-team processes with peer VPs of Engineering under the CTO
Manage strategic software vendor and third-party partner relationships
Implement and continuously refine Agile processes to increase delivery velocity and product quality

Requirements

What you’ll need

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 where speed and adaptability are critical
Demonstrated experience leading engineering team members globally having deep familiarity with 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 (Amazon Web Services)
Experience actively implementing and driving engineering teams to adopt AI-driven development practices (e.g., Claude Code) to improve workflow and output
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