Checkmate · 14 hours ago
Head of Data Science - Product Experimentation & Machine Learning
United States
Full-time
Remote
Lead/Staff, Director/Executive
$200K/yr - $260K/yr
8+ years expCheckmate builds the operating system for digital ordering in restaurants, and they are seeking a Head of Data Science to lead product experimentation and machine learning initiatives. This role involves designing, running, and scaling machine-learning-driven experiments to enhance ordering accuracy and automation quality while collaborating with Product, Engineering, and Data teams.
E-CommerceFood and BeverageMobile PaymentsPaymentsRestaurants
Responsibilities
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
Qualification
Required
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
Preferred
Experience with experiment platforms or building internal tooling for experimentation and model evaluation
Experience deploying ML models into high-volume transactional systems
Experience working with NLP, LLMs, or automation systems
Experience with multi-modal or operational data (e.g., orders, text, voice, or system events)
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
Company
Checkmate
Checkmate is a service in integrating 3rd party delivery platforms directly into POS systems.
201-500 employees
H1B Sponsorship
Checkmate has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2024 (1)
Funding
Current Stage
Growth StageTotal Funding
$13MKey Investors
Tiger Global Management
2024-10-23Series B· $10M
2018-11-12Series A· $3M
Leadership Team
Vishal Agarwal
Founder & CEO
Luke Ivers
CTO
Recent News
Company data provided by crunchbase