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ItsaCheckmateIT

Senior Prompt Engineer-Data Science & Quality Analysis

Checkmate, formerly ItsaCheckmate, provides a comprehensive suite of digital ordering solutions for enterprise restaurant brands, integrating third-party and first-party ordering, menu management, and analytics.

ItsaCheckmate

Employee count: 201-500

Salary: 145k-160k USD

United States only

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As a Senior Prompt Engineer focused on Data Science and Quality Analysis, you’ll design, test, and evaluate prompts for AI systems that interact with real-world restaurant data. You’ll work cross-functionally to develop AI solutions that drive operational efficiency, improve data interpretation, and support smarter decision-making for restaurant operators.

Your work will directly influence how AI models perform in high-stakes, dynamic environments such as order processing, reporting, support automation, and performance analysis.

  • Proven experience in prompt engineering and working with LLMs (GPT-4, Claude, Gemini, and LLaMA) for text generation, reasoning, and structured data extraction.
  • Proficiency in Python and SQL for data analysis, evaluation scripting, and workflow automation.
  • Strong background in A/B testing, statistical analysis, and performance metrics

evaluation, with the ability to design experiments and interpret data-driven insights for continuous model optimization.

  • Familiarity with prompt-evaluation tools such as LangFuse or Galileo, and Weights and Biases for experiment management and regression testing.
  • Deep understanding of advanced prompting techniques, including few-shot prompting, reasoning-based prompting, multi-turn dialogue design, agentic orchestration, and DSPy/AdaFlow-style programmatic prompting frameworks.
  • Experience applying CO-STAR and TIDD-EC! prompting frameworks for structured reasoning, instruction design, and context control in production-grade LLM systems.
  • Excellent requirement-elicitation and communication skills, with the ability to translate business objectives into prompt engineering solutions.
  • Analytical mindset with a process-driven approach to optimizing model behavior, data quality, and operational workflows.
  • Design, test, and optimize LLM prompts for conversational AI, text classification, and structured data extraction tasks.
  • Build evaluation pipelines to analyze prompt performance using quantitative metrics, human-in-the-loop feedback, and business KPIs.
  • Conduct prompt experiments and regression testing to ensure stability, accuracy, and safety as models evolve.
  • Collaborate with Machine Learning, Product, and Operations teams to translate business objectives into scalable, data-driven prompt-engineering strategies that enhance model accuracy, efficiency, and real-world usability.
  • Use Python/SQL to analyze model outputs, identify anomalies, and automate quality checks.
  • Document best practices and contribute to internal frameworks for prompt evaluation and continuous improvement.
  • Communicate findings effectively to technical and non-technical stakeholders, driving measurable business impact through insight-driven decisions.

100% Remote

Salary $145,000 - $160,000

Requirements

  • B.S. or higher in a quantitative discipline (Data Science, Computer Science, Engineering, or related field) or in a field relevant to language models (Linguistics, Philosophy, Cognitive Science, etc.).
  • 5+ years of relevant experience with a B.S. degree, or 3+ years of experience with a Master’s degree.
  • Demonstrated proficiency in Python for automation, evaluation, and experimentation with LLM workflows.
  • Academic or applied research experience related to language models, prompt engineering, or LLM-based systems is a strong plus.
  • Familiarity with LLM architectures, embeddings, and fine-tuning techniques preferred.
  • Experience with LLM red-teaming, adversarial evaluation, or model safety testing is a plus.

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
  • Stock Option Plan

About the job

Apply before

Posted on

Job type

Full Time

Experience level

Senior

Salary

Salary: 145k-160k USD

Location requirements

Hiring timezones

United States +/- 0 hours

About ItsaCheckmate

Learn more about ItsaCheckmate and their company culture.

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At Checkmate, formerly ItsaCheckmate, we are spearheading a new era of restaurant technology through groundbreaking innovations designed to empower enterprise brands and streamline their digital operations. Our journey began in 2016 with a singular vision: to solve the complexities of online ordering and integration for restaurants. Recognizing the critical need for a unified platform, we've evolved from an order integration specialist into a comprehensive digital ordering supplier. Our technology facilitates the seamless management of sales across diverse channels, encompassing first-party to third-party ordering platforms, and provides centralized business management tools. This enables restaurant businesses to optimize their ordering processes and significantly improve operational efficiency.

Through relentless innovation, Checkmate offers a scalable technology suite that allows restaurants to drive sales through various avenues, including custom websites, mobile applications, kiosks, catering services, third-party marketplaces, and cutting-edge voice AI. We are committed to helping brands conquer their digital aspirations with seamless integrations, intelligent analytics, and round-the-clock service. Our platform empowers restaurants to launch distinctive ordering experiences, centrally manage menus, recapture lost revenue, harness valuable customer data, and continuously adapt with new integrations. The recent acquisition of VoiceBite, an AI voice ordering technology provider, and Open Tender, a first-party ordering and guest engagement platform, underscores our dedication to providing a truly unified and advanced ordering experience. We are not just focused on solving today's challenges but are proactively anticipating and addressing the technological needs of tomorrow, helping our partners expand their digital footprint and build stronger customer connections.

Employee benefits

Learn about the employee benefits and perks provided at ItsaCheckmate.

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Medical Insurance

Competitive salary and benefits package-medical, dental, vision, 401K, etc.

Dental Insurance

Competitive salary and benefits package-medical, dental, vision, 401K, etc.

Vision Insurance

Competitive salary and benefits package-medical, dental, vision, 401K, etc.

401K

Competitive salary and benefits package-medical, dental, vision, 401K, etc.

View ItsaCheckmate's employee benefits
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