Head of Data Science - Product Experimentation & Machine Learning

About Checkmate
Checkmate is a restaurant technology solution provider that has continually evolved over time. We started in 2017 by integrating 3rd party platforms to the POS systems of restaurants. At that time, there were multiple 3rd party platforms like GrubHub, UberEats, DoorDash, Postmates, Caviar, and even Amazon!
This was the photograph that started it all!

We have since then continually evolved to add multiple products to our portfolio, the primary ones being first party ordering solutions like web and app ordering, kiosks and catering. We have now recently moved into three new exciting products: Digital Menu Boards, Phone Ordering AI and Drive thru AI. We form a very core part of the restaurant technology ecosystem, and are continually adding more and more digital solutions for the restaurant brands to increase their sales.

Our revolutionary enterprise menu management system, Everyware, truly unlocks the potential of menus and how it can be customized for each individual digital channel. As you can see, this is a company that continually evolves and adapts and today we are powering digital ordering solutions for some of the largest brands in the world.

We have been called the "north star of vendors" as we truly believe that technology is just a method by which we service the customers, it does not form the entirety of it. Service is a big component of what we provide to our customers, which is inherently believed by every single team member here. We are doing a lot of exciting things, including application of AI in our products and systems, using experimentation at scale to determine what works for our clients and ML to analyze and productize the massive amount of data we have. Each individual here makes a difference and has a valuable contribution. Key traits here are ownership and drive. Join us if you think you have them.

Role Overview
Given the direction technology is moving in this era, the lines between data science and product are blurring very quickly. We are looking for a strategic leader who can successfully wear both hats. This role will involve a very heavy involvement on the product side as well, with an analytics mindset. Two of our largest growth drivers have a very strong element of data science present, and this person will be involved in the growth and development of those products.

In this role, you will work closely with the CEO, CTO, SVP of Engineering and Product managers to setup the core framework on how these products are built and their metrics tracked and measured. You will architect and scale the experimentation and analytics infrastructure that powers product decision-making across the company, from designing rigorous A/B testing frameworks to developing machine learning models that guide product strategy. Your work will sit at the center of how we innovate, enabling teams to move faster while making confident, data-informed decisions that improve the platform.

This is a rare opportunity to build something foundational. You will help shape the future of Checkmate’s data team by building and mentoring a team of analytics engineers and data scientists to support the company’s next stage of growth. And you will lay the path for the data science team to be embedded as a core part of the product team, with an opportunity in the future to have each product supported by a team of data scientists. You will lay the groundwork for the data pipeline for these new products, what metrics are tracked and how they are tracked.

One of the core products we are developing is deep rooted in A/B experimentation. We are looking for this leader to provide strategic guidance and direction on setting up the A/B experimentation in the company, which will be applied not only to this product but to multiple other products in the company.
The role blends strategic leadership along with deep hands-on technical work by partnering closely with Product, Engineering, and Data leaders to turn ambitious ideas into controlled experiments, develop predictive models that drive decision-making, and translate insights into meaningful product and roadmap outcomes.

Success in this role requires comfort operating at multiple altitudes—defining experimentation strategy, innovating on analytics infrastructure, and diving into complex data and modeling problems when needed. In a high-volume production environment like ours, even small improvements can drive significant gains in ordering accuracy, automation quality, conversion, reliability, and merchant success across the platform.

If you’re excited about building teams and systems that enable smarter product decisions, scaling experimentation across a fast-growing platform, being a core part of the product team, and creating measurable impact through data, this role will give you the autonomy and scope to do exactly that.

100% Remote

• Review and set up the core analytics infrastructure of the company, in close partnership with the CTO. We are looking to build this from scratch
• Set up the A/B experimentation framework / architecture on which multiple products in the company can run.
• 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.
• Hire, lead, and mentor data scientists and analysts, setting standards for experimentation, modeling, and evaluation across the organization.

• 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.

• 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).

• 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