Vice President of Engineering

🔥 13 hours ago

🇺🇸 United States – Remote

⏰ Full Time

🔴 Lead

👔 Vice President

👻 Ghost score 10%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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ItsaCheckmate

WebsiteLinkedInAll Job Openings

201 - 500 employees

📦 Logistics

💼 Consulting

📣 Marketing

Logistics • Consulting • Marketing

ItsaCheckmate is a technology company that provides powerful ordering solutions for busy restaurants. Their platform enables restaurants to drive sales and connect with customers through various ordering channels, including web, app, kiosk, and third-party integrations. With its scalable enterprise technology, ItsaCheckmate helps restaurants manage and streamline operations, reduce order errors, and increase productivity. They offer features such as loyalty programs, catering management, QR-code ordering, and unified channel management. Trusted by over 2,400 brands, ItsaCheckmate is dedicated to supporting restaurant growth with innovative digital solutions and a marketplace of integrations.

📋 Description

• 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

• 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