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.

Checkmate is recruiting for a Senior Full Stack Engineer to join our Engineering team helping to engineer, operate, and grow our unique web-based restaurant-tech SaaS platform using AI technologies.  In this role you will partner closely with our Product team and other Engineering team members to drive innovative new features, software improvements, and architectural agility supporting our product roadmap within our product-led Engineering organization that services both internal and external customers.  This role is ideal for a senior level engineer who has experience leading other team members designing and coding on enterprise level Python applications, and someone who is comfortable breaking down complex problems into iterative deliverables using advancements in AI to ship faster. Additionally, Checkmate is a 100% remote based and globally distributed organization!

On the Checkmate Engineering Team you’ll have the opportunity to use cutting edge technologies in an AI-led SDLC environment to lead initiatives that grow, modernize, and scale core parts of our product platform.  You’ll own features end-to-end, drive architectural improvements, and help elevate the technical bar across the team. 

100% Remote

$180,000 - $190,000

Essential Job Functions

Full Stack Development: 

• Collaborate with Product, Design, and Engineering teams to design, build, test, deploy, and maintain scalable web applications 
• Leverage AI coding agents to accelerate product development and defect resolution
• Develop and maintain RESTful and/or GraphQL APIs
• Develop asynchronous application processing using tools like Sidekiq
• Build and maintain responsive, high-performance React.js interfaces and reusable components
• Write and optimize SQL queries across PostgreSQL/MySQL databases

Architecture and Design: 

• Improve application reliability, scalability, and long-term maintainability of large enterprise systems
• Create, and collaborate with other engineers on, technical specifications aligned against short term and long term Product roadmaps and enterprise architectural goals
• Use APM and observability tools to detect, diagnose, and fix performance bottlenecks 
• Identify technical debt and drive practical solutions to pay down debt

End-to-End Feature Ownership: 

• Own features and complex issues from product design through development, deployment, and monitoring. 
• Participate in all parts of the Product, Design, and Engineering processes building new features together in a collaborative pod-based environment
• Interact with our internal customers using your contributions to our software platform in support of our external customers

Leadership Opportunities: 

• Work with team members to identify, prioritize, and reduce technical debt and improve scalability and performance across the codebase
• Participate in architecture and technical design discussions across Product and Engineering
• Contribute to peer code reviews, automated testing, CI/CD pipelines, and deployment workflows
• Investigate and resolve outages with root-cause analysis and clear follow-up improvements
• Mentor junior engineers and promote engineering best practices using AI-led practices

Requirements

Education Requirements

• Bachelor’s degree in Computer Science, Engineering, or equivalent practical experience

Professional Experience Requirements

• 8+ years of experience building enterprise level applications using Python.
• 3+ years working with React.js or a related modern javascript frameworks
• 3+ years working working within a 30+ team member sized engineering team
• 3+ years working 100% remote and a desire to continue working remotely
• 3+ years developing and operating applications on AWS
• 2+ years developing using AI coding agents including Claude Code or Codex

Technical Skill Requirements

• Experience working using Docker locally 
• Experience running enterprise level production workload apps on AWS
• Experience integrating with RESTful and GraphQL APIs
• Experience write raw SQL queries in a relational database 
• Experience building asynchronous background job process across multiple tools/frameworks
• Experience with observability tools like Datadog, Sentry, or New Relic
• Experience writing automated unit tests having > 60% code coverage
• CI/CD development experience creating Github Actions 
• Experience modernizing legacy Python applications

Team and Work Style Requirements

• Experience working in product led engineering organization 
• Experience working in a multi-team / pod-based engineering team
• Works with an accountability and ownership mindset and calls out gaps where they exist
• Experience working in high-volume transactional production environments
• Exceptional at translating product requirement documents into detailed technical specifications
• Work US Eastern Timezone hours between 9am - 5pm ET

Benefits

• Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (401k)
• Life Insurance (Basic, Voluntary & AD&D)
• Flexible Paid Time Off
• Family Leave (Maternity, Paternity)
• Short Term & Long Term Disability
• Training & Development
• Work From Home