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Head of Data Science - Product Experimentation & Machine Learning

2 hours, 21 minutes ago
United States
Full-time
Lead
Data Scientist
Data Science and Analytics
LLM Machine Learning NLP Python SQL
Apply Now
ItsaCheckmate

ItsaCheckmate

ItsaCheckmate simplifies digital orders and menu management for restaurants by integrating with various platforms directly into the POS, eliminating the need for tablets and manual transfers. Operators benefit from increased order volume, reduced error...

Hotels, Restaurants & Leisure
51-250
Founded 2016
$3M raised
View All Jobs 7

Description

  • Own end-to-end product experimentation, including hypothesis generation, metric definition, experimental design, analysis, and executive-level interpretation.
  • Design and maintain ML-powered evaluation frameworks for product changes, automation quality, and system reliability.
  • Build and deploy predictive models, classifiers, and ranking systems to support experimentation, personalization, and product optimization.
  • Partner with Product and Engineering to test new features, workflows, and ML models through controlled experiments and incremental rollouts.
  • Lead offline and online model evaluation using rigorous statistical methods to compare baselines, candidate models, and product variants.
  • Apply causal inference and quasi-experimental methods when randomized experiments are not feasible.
  • Develop experiment pipelines and instrumentation, including logging, dashboards, monitoring, and automated analysis.
  • Perform failure-mode and error analysis to guide product iteration and model improvement.
  • Translate experiment outcomes into clear product decisions and influence roadmap prioritization and system design.
  • Lead and mentor data scientists and analysts, setting standards for experimentation, modeling, and evaluation.

Requirements

  • 8–12+ years of experience in data science, machine learning, or applied experimentation roles.
  • Demonstrated expertise in product experimentation and A/B testing, including design, execution, and statistical evaluation.
  • Strong background in machine learning, statistical modeling, and causal inference applied to real-world products.
  • Experience building and evaluating predictive models, classifiers, or ranking systems in production environments.
  • Proven ability to operate in both startup-style experimentation and scaled product ecosystems.
  • Experience leading teams, setting technical direction, and delivering cross-functional impact.
  • Excellent coding skills in Python or similar languages, strong SQL skills, and experience building data pipelines or ML systems.
  • Ability to connect technical findings to product and business outcomes.
  • Strong communication skills with technical and non-technical stakeholders.
  • Experience with experiment platforms or building internal tooling for experimentation and model evaluation (preferred).
  • Experience deploying ML models into high-volume transactional systems (preferred).
  • Experience working with NLP, LLMs, or automation systems (preferred).
  • Experience with multi-modal or operational data such as orders, text, voice, or system events (preferred).

Benefits

  • Health, dental, and vision insurance.
  • 401(k) retirement plan.
  • Basic, voluntary, and AD&D life insurance.
  • Flexible paid time off.
  • Family leave, including maternity and paternity leave.
  • Short-term and long-term disability coverage.
  • Training and development support.
  • Work-from-home flexibility.
  • Stock option plan.

Interested in this position?

Apply directly on the company website

Apply Now

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