Job Description

Checkmate is building advanced Voice AI systems for some of the largest restaurant brands in the United States, including several in the top ten. Our AI solutions are live today in production with real customers, consistently achieving over 80 percent accuracy. This represents a 1 billion dollar market opportunity, and we are on track to scale to multiple thousand stores in the next 24 months. Join us at this pivotal moment of growth to shape AI products used daily by thousands of staff and customers, bringing together cutting-edge LLM innovation with meaningful real-world business impact.
As a Senior Python Engineer, you will play a central role in designing and building the backend systems that power Checkmate's real-time Voice AI platform. You will work across core services, infrastructure, and AI-driven components to ensure the system is reliable, scalable, and optimized for production environments with demanding operational requirements. This role requires an engineer who is comfortable owning substantial components of the platform, contributing to architectural decisions, and delivering software that directly supports mission critical applications used in thousands of restaurant locations. You will collaborate closely with Machine Learning, Product, and Operations teams to translate complex technical needs into stable, maintainable, and high-performance systems that move the business forward.
Requirements

• Bachelor's Degree in Computer Science, Engineering, or related technical fields.
• At least 7 years of hands-on Python experience building production grade systems and services.
• Strong background in FastAPI development, distributed systems, and backend architecture.
• Experience integrating AI or ML systems into production environments, including workflows involving LLMs or NLP components.
• Proficiency with CI and CD technologies, containerization, and deploying services to AWS and Azure.
• Strong understanding of data structures, type hinting, asynchronous programming, testing practices, and system performance optimization.
• Experience working orchestration platforms for product access to AI systems.
• Ability to communicate technical decisions clearly to cross functional stakeholders.

• Architect, build, and maintain Python based backend services that support real-time Voice AI workflows across production environments.
• Collaborate with Machine Learning engineers to integrate LLM and GenAI driven components into scalable application pipelines.
• Develop robust APIs, internal service interfaces, and orchestration layers that support high throughput drive-thru and retail operations.
• Implement and maintain CI and CD pipelines to ensure reliable, automated delivery of backend systems and AI powered services.
• Optimize system performance, reliability, and fault tolerance across distributed environments running on AWS, GCP, or Azure.
• Contribute to model testing, monitoring, and validation workflows that ensure platform stability under real-world load.
• Build prototypes and internal tooling that accelerate experimentation, data analysis, and platform iteration.
• Participate in code reviews, design discussions, and cross-functional planning to ensure engineering quality and alignment with product goals.

Desired Qualifications

• Experience working with real-time or high throughput systems.
• Familiarity with MLOps workflows or model deployment pipelines.

Exposure to LLM frameworks, inference infrastructure, or agent driven systems. * Experience building tools or internal platforms that support engineering and machine learning teams

• Background in operational monitoring, observability, and reliability engineering.

Skills Required