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ItsaCheckmateIT

Senior/Staff Data Scientist - Product Experimentation & Evaluation (LLMs & AI)

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: 120k-260k USD

United States only

You will be a strategic partner to product, engineering, and trust and safety teams, responsible for defining evaluation frameworks, leading experiments (A/B, quasi-experiments, etc.), and turning offline and live model performance into product improvements. This role requires a strong track record in startup-style experimentation (moving quickly with scrappy but rigorous methods) and product experimentation at scale. The ideal candidate will also bring proven experience in leading and managing teams to deliver high-impact data science work.

100% remote

Salary Range $120,000 - $260,000

Essential Job Functions

●Lead end-to-end experimentation: hypothesis generation, metric design, experiment design (A/B, multivariate, sequential, etc.), analysis, and interpretation.

●Build and maintain evaluation frameworks for LLMs: correctness, consistency, safety, hallucination detection, bias/fairness, etc.

●Develop predictive models, classification/ranking systems, and heuristics to improve product features related to AI/language generation.

●Collaborate with prompt engineers & model builders to test prompt strategies, fine-tuning, or model selection; work on failure modes/error analysis.

●Automate experiment pipelines: dashboards, monitoring, alerting, instrumentation. Ensure data quality & measurement integrity.

●Use causal inference / observational studies when randomized experiments are not feasible.

●Present findings and recommendations to both technical and non-technical leadership; influence roadmap decisions.

●Drive experimentation in startup-like environments: rapid iteration, learning from limited data, and balancing speed with rigor.

●Shape large-scale product experimentation: define frameworks for experimentation at scale and integrate results into product strategy.

●Lead and mentor teams of data scientists, analysts, and engineers; set best practices for experiment design and AI product evaluation.

Requirements

  • ~8-12+ years of experience in data science / ML roles, ideally with experiment design/product analytics.
  • Proven track record in both startup-style and large-scale product experimentation.
  • Experience leading teams, setting strategy, and driving execution in cross-functional environments.
  • Strong background with statistical methods, causal inference, and rigorous measurement.
  • Experience using LLMs / NLP / AI / prompt engineering or a closely related field.
  • Excellent coding skills in Python (or similar), strong SQL, experience building and deploying models or analytic pipelines.
  • Ability to work in cross-functional teams, translate technical results into business or product changes.
  • Strong communication skills; ability to explain complex analyses to non-technical stakeholders.

Preferred Qualifications

  • Experience fine-tuning or working with multiple LLM providers / APIs.
  • Experience with experiment platforms or building internal tooling for experimentation & model evaluation.
  • Experience in voice / ASR or other multi-modal data.

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: 120k-260k 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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ItsaCheckmate hiring Senior/Staff Data Scientist - Product Experimentation & Evaluation (LLMs & AI) • Remote (Work from Home) | Himalayas