Vice President of Engineering

About Checkmate

Checkmate is a restaurant technology solution provider that has continually evolved over time. We started in 2017 by integrating 3rd party platforms to the POS systems of restaurants. At that time, there were multiple 3rd party platforms like GrubHub, UberEats, DoorDash, Postmates, Caviar, and even Amazon!

This was the photograph that started it all!

We have since then continually evolved to add multiple products to our portfolio, the primary ones being first party ordering solutions like web and app ordering, kiosks and catering. We have now recently moved into three new exciting products: Digital Menu Boards, Phone Ordering AI and Drive thru AI. We form a very core part of the restaurant technology ecosystem, and are continually adding more and more digital solutions for the restaurant brands to increase their sales.

Our revolutionary enterprise menu management system, Everyware, truly unlocks the potential of menus and how it can be customized for each individual digital channel. As you can see, this is a company that continually evolves and adapts and today we are powering digital ordering solutions for some of the largest brands in the world.

We have been called the "north star of vendors" as we truly believe that technology is just a method by which we service the customers, it does not form the entirety of it. Service is a big component of what we provide to our customers, which is inherently believed by every single team member here. We are doing a lot of exciting things, including application of AI in our products and systems, using experimentation at scale to determine what works for our clients and ML to analyze and productize the massive amount of data we have. Each individual here makes a difference and has a valuable contribution. Key traits here are ownership and drive. Join us if you think you have them.

About the Role

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. These cover delivery (deployment frequency, lead time for changes, change failure rate, time to restore service), quality (escaped defects, test coverage, incident volume), predictability (commitment accuracy, cycle time), and team health (engagement, on-call load, attrition).
• Run a regular continuous improvement cycle, including retrospectives, post-incident reviews, and quarterly process assessments. Turn findings into prioritized, owned improvement initiatives with measurable outcomes.
• Measure the impact of AI-assisted development tools (e.g., Claude Code, AI code review, automated test generation) on velocity, quality, and developer experience. Use the results to refine adoption practices and guidance.
• Maintain a sustainable balance between feature delivery, technical debt remediation, and operational work through explicit capacity allocation and regular roadmap trade-off discussions with Product.

Cross-Functional Collaboration & Process

• Work closely with Product Management, Data Analytics, and Customer Success teams to align technical roadmaps with business objectives, user experience goals, and feature releases.
• Collaborate with peer VPs of Engineering under the CTO to establish consistent engineering standards, shared technical frameworks, and cross-team processes.
• Manage strategic software vendor and third-party partner relationships (e.g., outsourced talent, specialized tools) 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.

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.