ItsaCheckmate

Head of Data Science – Product Experimentation, Machine Learning

ItsaCheckmate

full-time

Posted on:

Location Type: Remote

Location: United States

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About the role

  • Own end-to-end product experimentation: hypothesis generation, metric definition, experimental design (A/B, multivariate, sequential testing), analysis, and executive-level interpretation.
  • Design and maintain ML-powered evaluation frameworks for product changes, automation quality, and system reliability (e.g., order accuracy, routing, error rates, conversion).
  • Build and deploy predictive models, classifiers, and ranking systems that power 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, comparing baselines, candidate models, and product variants using rigorous statistical methods.
  • Use causal inference and quasi-experimental methods when randomized experiments are not feasible.
  • Develop experiment pipelines and instrumentation: logging, dashboards, monitoring, and automated analysis to ensure measurement integrity.
  • Perform failure-mode and error analysis to guide product iteration and model improvement.
  • Translate experiment outcomes into clear product decisions, influencing roadmap prioritization and system design.
  • Drive experimentation at scale in a fast-moving environment, balancing speed, rigor, and business impact.
  • Lead and mentor data scientists and analysts, setting standards for experimentation, modeling, and evaluation across the organization.

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), strong SQL, 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.
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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
product experimentationA/B testingmultivariate testingsequential testingmachine learningstatistical modelingcausal inferencepredictive modelsdata pipelinesSQL
Soft Skills
leadershipmentoringcommunicationcross-functional collaborationanalytical thinkingproblem-solvinginfluencingdecision-makingadaptabilityteamwork