Checkmate

Build, optimize, and troubleshoot lifecycle marketing flows and campaigns across multiple channels to support revenue growth. | 2-4 years of hands-on experience with CRM tools like Klaviyo, Braze, or Attentive, and a solid understanding of ecommerce metrics and operational workflows. | About Checkmate Checkmate is an AI marketing platform modernizing eCommerce by enabling smarter, more connected buying experiences between brands and consumers. Our platform resolves anonymous traffic, enriches customer data, and activates high-intent audiences across onsite, owned, and paid channels—unlocking net-new revenue brands can’t access on their own. We offer three core products: Enrichment – Resolve anonymous visitors and power lifecycle flows Targeting – Deliver single-use offers across high-performing surfaces Audiences – Capture pre-checkout emails and turn into competitive insights Role Overview We’re hiring a performance-driven operator who loves building, improving, and optimizing the systems that power revenue. This role is deeply executional: you will configure flows, implement updates across CRM and paid channels, monitor performance, run tests, and ensure brands are set up to get the full value of Checkmate’s products. You’ll support the performance work that sits at the center of our business—turning identity data, shopper behavior, and product signals into clean, accurate, high-impact execution. You’ll support senior team members handling strategy and client-facing conversations with the performance that actually makes it all happen. If you enjoy tinkering, experimenting, tightening flows, and seeing your execution influence revenue lift, this role will be energizing. What You’ll DoBuild & Maintain Lifecycle Flows Create, update, and QA Klaviyo/Braze/Attentive flows for Enrichment Implement segmentation logic, event triggers, and timing rules Refresh creative components, templates, and conditional logic Ensure flow performance aligns with best practices provided by team leads Performance Optimization Execution Monitor channel-level and flow-level performance to spot trends Implement optimizations and variations - adjust messaging, timing, and targeting to support A/B and multivariate tests Support implementation of experiments across email, SMS, onsite widgets, and other surfaces Update paid channel creative, copy, or settings when needed to keep performance tight Operations & Configuration Manage CRM setups, integrations, tagging, and data hygiene Keep brand configurations accurate across channels and surfaces Troubleshoot delivery issues, sync inconsistencies, or flow errors Maintain documentation, setup checklists, and workflow guides Cross-Functional Execution Work closely with team leads to translate performance insights into execution steps Collaborate with Product, Engineering, and Data when technical adjustments are needed Surface operational issues or performance anomalies internally Build for Scale Help standardize templates and reusable flow components Improve execution workflows and reduce manual steps Contribute to internal playbooks and repeatable performance processes Why This Role Matters Your execution is what turns our product into performance. When flows fire correctly, tests run smoothly, ads stay fresh, and operational details are tight, brands feel the impact and so does our revenue. You’ll be a foundational part of how we deliver high-quality results at scale. Can’t wait to chat with you! What You Bring 2–4 years in CRM execution, lifecycle operations, technical marketing production, or performance marketing support Hands-on experience with Klaviyo, Braze, Attentive, or similar CRM tools Familiarity with ecommerce metrics (AOV, GMV, CPA, funnel behavior, deliverability) Strong organizational and operational instincts Ability to interpret performance data and apply the right operational changes Bonus: experience updating paid social ads, audience targeting, or onsite conversion tools Note: If you think you can “rock” this roll, just apply. I promise we’ll read every resume and consider everyone. Pay & Benefits Salary range ($100,000 - $130,000) + bonus Equity Healthcare + dental + vision 401k Company retreats 4 weeks PTOs and health days Gym membership comped US remote - Los Angeles or New York City preferred

Manage and grow agency partnerships, develop pitch materials, and track partner performance to drive revenue growth. | 3-6 years in email marketing, partnerships, or growth marketing, with experience working through marketing agencies and strong analytical skills. | About Checkmate Checkmate is a consumer app and data company that helps brands connect with shoppers more effectively. Using real-time shopping behavior through our proprietary data network, we help brands target, retarget, and convert high-intent customers — while ensuring shoppers get the best value on every purchase. We’ve: Been the #1 app in the App Store twice Built a user base of millions actively seeking personalized deals Enabled hundreds of brands to drive retention and engagement through our commerce channels (app, browser extension, email, SMS) Our mission is to reshape how shoppers discover value — and how brands build loyalty — by bridging content, commerce, and data. About the Role We’re looking for a Strategic Partnerships Manager to help us grow and manage our agency relationships — including retention, lifecycle, and performance marketing agencies to work with more brands. This role is perfect for someone with deep relationships in the email marketing world, but ready to move fast, hustle hard, and make a big impact. You’ll be on the front lines— prospecting brand partners, onboarding new strategic partners, and ensuring Checkmate is top of mind for client and network strategies. What You’ll Do Success in this role to both use data and relationships to expand our brand relationships and grow revenue with our existing brand partners. Partner Development Identify, source, and onboard new agency partners (retention, lifecycle, performance marketing, affiliate, email) Build relationships with account managers at top agencies Use data to identify high value brands we can optimize and upsell Develop pitch materials and co-marketing campaigns to support partner acquisition and engagement Relationship Management Act as day-to-day point of contact for agency relationships Regularly check in with partners to ensure Checkmate is part of client campaigns Organize trainings, enablement sessions, and strategy syncs with agencies and platforms Growth & Operations Track and report on partner performance, pipeline, and coverage Coordinate with internal Sales, Ops, and Marketing to support partner initiatives Help evolve our partnerships playbook and tooling Who You Are Loves start-ups and thinks like an owner / founder 3–6 years of experience in email marketing, partnerships, or growth marketing Hands-on experience working with or through marketing agencies is required (bonus points for existing connections with Klaviyo/Shopify agencies + DTC e-commerce brands) Strong analytics and data ability Strong communicator — able to tell a compelling story and hold your own in agency meetings High-energy, self-starter mentality — thrives in fast-paced, scrappy startup environments Comfortable managing multiple relationships and partner needs simultaneously Why Join Checkmate? Be part of a team reinventing shopper-brand relationships Own core parts of a high-leverage GTM motion early in your career Work with experienced founders and sales leaders Tons of growth opportunity Benefits Healthcare + dental + vision 401(k) 4 weeks PTO + health days Gym membership reimbursement US Remote-friendly, with hubs in NYC and LA Regular offsites and team retreats

Own and scale product experimentation and ML evaluation frameworks, build predictive models, and translate results into product decisions. | Over 8 years of experience in data science or experimentation, expertise in ML, statistical evaluation, Python, SQL, and experience leading teams. | Head of/Staff Data Scientist – Product Experimentation & Machine Learning About Checkmate Checkmate builds the operating system for digital ordering in restaurants, powering integrations between POS systems, delivery platforms, and restaurant brands. Our products sit at the center of how millions of orders move across systems every day — which makes experimentation, automation, and ML-driven optimization core to our competitive advantage. Role Overview You will be the technical and strategic owner of Checkmate’s product experimentation and evaluation stack. Your mission is to design, run, and scale machine-learning-driven experiments that improve ordering accuracy, automation quality, conversion, reliability, and merchant success across the platform. This role will require a blend of both strategic and hands on work. This person will be expected to be comfortable getting their hands in the weeds! You will partner closely with Product, Engineering, and Data to turn ideas into controlled experiments, build predictive models to power decision-making, and translate results into product and roadmap decisions. This role blends ML, causal inference, and A/B testing in a high-volume, production environment where small improvements generate massive real-world impact. 100% Remote Essential Job Functions 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. 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 Qualifications 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

Architect and build the conversation orchestration service for a voice AI platform. Write robust, asynchronous Python code to handle high concurrency and ensure system resilience. | Deep Python expertise with 5+ years in production systems is required. Candidates should also have strong database fundamentals and a solid understanding of networking and I/O. | We are developing a real-time voice AI platform that combines speech recognition, LLM-driven reasoning, and natural-sounding text-to-speech capabilities. This is production-grade software designed to run continuously, scale under heavy load, and deliver human-like conversations with minimal latency. If you are a seasoned Python engineer who thrives on building resilient systems and solving tough concurrency challenges, this is the role for you. What You’ll Do/Essential Job Functions ● Architect and build the conversation orchestration service: ASR → LLM inference → TTS streaming in real time ● Write robust, asynchronous Python code designed to handle high concurrency without deadlocks, race conditions, or memory leaks ● Design and maintain clean, well-structured APIs for future scalability and ease of debugging ● Manage interaction data using SQL Alchemy (or equivalent) with efficient schema design and safe migrations ● Implement observability: structured logging, metrics, and tracing across the system for instant issue diagnosis ● Partner with ML and Product teams to rapidly iterate on conversation flow and user experience ● Enforce a strong testing culture: automated unit tests, E2E flows, and load testing ● Build resilient systems capable of handling real-world edge cases like noisy audio, unreliable APIs, and flaky networks ● Continuously profile, optimize, and reduce latency and response times 100% Remote Salary $150,000 - $230,000 Deep Python expertise: 5+ years in Python, production systems experience required, context managers, generators, event loops, GIL, and effective use of asyncio Database fundamentals: data modeling, efficient queries, ORM best practices Networking & I/O: streaming, backpressure, and resilient design for unreliable networks Testing discipline: delivering production-ready, validated code Observability mindset: metrics, logs, and traces are integral to your coding process Production readiness: You’ve built and supported systems running live at scale. 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

Develop and deploy AI models to enhance restaurant technology. Collaborate with teams to create AI solutions tailored for the restaurant industry. | Candidates should have a strong background in computer science or engineering with over 3 years of experience in AI/ML. Proficiency in Python and familiarity with LLMs like GPT and LLama3 is essential. | As a Senior Software Engineer AI/ML specialized in Large Language Models (LLMs), you will play a pivotal role in developing and deploying state-of-the-art AI models to supercharge restaurants with advanced conversational capabilities, personalized recommendations, and intelligent automation. This role offers the chance to build new products from scratch, significantly influence product direction and engineering roadmap, and impact the future of restaurant technology. Your work will improve customer interactions, ensuring a seamless and delightful experience. Essential Job Functions Develop machine learning algorithms, focusing on Large Language Models (LLMs) like GPT, to improve accuracy and performance. Work with teams to turn business requirements into AI solutions. Use LLMs for restaurant-specific applications like real-time text generation and recommendation engines. Monitor and improve model performance. Stay up to date on the latest in machine learning and contribute to research and patents. Experiment with new methods like transfer learning and reinforcement learning. Collaborate with partners to integrate the latest AI innovations. 100% Remote Salary $160,000 - $190,000 Strong background in computer science or engineering with 3+ years of experience. Knowledge of machine learning, deep learning, and natural language processing. Experience with LLMs like GPT and LLama3. Proficient in Python and familiar with TensorFlow or PyTorch. Good problem-solving skills and ability to work independently and in a team. Understanding of conversational English and experience with voice programs/products. Proficient in cloud services (AWS, Azure, Google Cloud) and container technologies (Docker, Kubernetes). Strong communication skills for explaining technical ideas to various audiences. Previous experience in the restaurant industry is a plus but not required. Ability to manage product specifications from concept to production. Understanding of software design principles, including optimization and performance tuning. Extensive understanding of fast food and quick service restaurants 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

Develop and deploy AI models to enhance restaurant technology. Collaborate with teams to create AI solutions tailored for the restaurant industry. | Candidates should have a strong background in computer science or engineering with at least 3 years of experience. Proficiency in machine learning, LLMs, and programming languages like Python is essential. | As a Senior Software Engineer AI/ML specialized in Large Language Models (LLMs), you will play a pivotal role in developing and deploying state-of-the-art AI models to supercharge restaurants with advanced conversational capabilities, personalized recommendations, and intelligent automation. This role offers the chance to build new products from scratch, significantly influence product direction and engineering roadmap, and impact the future of restaurant technology. Your work will improve customer interactions, ensuring a seamless and delightful experience. Essential Job Functions Develop machine learning algorithms, focusing on Large Language Models (LLMs) like GPT, to improve accuracy and performance. Work with teams to turn business requirements into AI solutions. Use LLMs for restaurant-specific applications like real-time text generation and recommendation engines. Monitor and improve model performance. Stay up to date on the latest in machine learning and contribute to research and patents. Experiment with new methods like transfer learning and reinforcement learning. Collaborate with partners to integrate the latest AI innovations. 100% Remote Salary $160,000 - $190,000 Strong background in computer science or engineering with 3+ years of experience. Knowledge of machine learning, deep learning, and natural language processing. Experience with LLMs like GPT and LLama3. Proficient in Python and familiar with TensorFlow or PyTorch. Good problem-solving skills and ability to work independently and in a team. Understanding of conversational English and experience with voice programs/products. Proficient in cloud services (AWS, Azure, Google Cloud) and container technologies (Docker, Kubernetes). Strong communication skills for explaining technical ideas to various audiences. Previous experience in the restaurant industry is a plus but not required. Ability to manage product specifications from concept to production. Understanding of software design principles, including optimization and performance tuning. Extensive understanding of fast food and quick service restaurants 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

You will design and evaluate algorithms to enhance speech and audio performance in our products. Additionally, you will prototype and research various software/hardware solutions involving audio, speech, speakers, and sensors for phone and drive-through interfaces. | A Master's or PhD or multiple years of industry experience in computer science or engineering is required. Candidates should have experience evaluating speech quality/recognition and building scalable systems for real-time audio input/output across multiple concurrent channels. | This position specializes in audio and digital signal processing for voice AI, and you will be instrumental in establishing the foundation for real-time audio processing and advanced conversational capabilities, particularly tailored to the restaurant industry. You will design and evaluate algorithms to enhance speech and audio performance in our products. Working closely with product and engineering teams, you will develop and assess new solutions, devising innovative ways to integrate them. Additionally, you will prototype and research various software/hardware solutions involving audio, speech, speakers, and sensors for phone and drive-through interfaces. 100% remote Salary range $140,000 - $220,000 Essential Job Functions Algorithm Development: Create, design, and troubleshoot real-time audio algorithms. Collaborative Engineering: Work within a multidisciplinary team to make essential architectural decisions for efficient software delivery. Software Creation: Develop software for various consumer devices with real-time audio inputs and outputs. Code Quality: Write clean, readable code, efficiently debug complex issues, and prioritize tasks to maintain high productivity. Continuous Learning: Engage in ongoing learning, explore new technologies, and stay updated on the latest audio and digital signal processing advancements. AI/ML Integration: Utilize AI/ML techniques for speech enhancement. Prototyping: Rapidly prototype new software and hardware solutions to contribute to product ideation and development. Master’s or PHD or multiple years of industry experience in computer science or engineering. Experience evaluating speech quality/recognition and building scalable systems for real-time audio input/output across multiple concurrent channels. Good understanding of voice activity detection (VAD), beamforming, source separation, and speaker diarization/separation. Interest in prototyping hardware solutions ranging from hobby to professional levels, and a strong sense of future-proofing regarding hardware decisions. Good problem-solving skills and ability to work independently and in a team. Understanding of conversational English and experience with voice programs/products. Strong communication skills for explaining technical ideas to various audiences. Ability to manage product specifications from concept to production. Extensive experience ordering food at fast food and quick service restaurants. 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

You will design and evaluate algorithms to enhance speech and audio performance in our products. Additionally, you will prototype and research various software/hardware solutions involving audio, speech, speakers, and sensors for phone and drive-through interfaces. | A Master's or PhD or multiple years of industry experience in computer science or engineering is required. Candidates should have experience evaluating speech quality/recognition and building scalable systems for real-time audio input/output across multiple concurrent channels. | This position specializes in audio and digital signal processing for voice AI, and you will be instrumental in establishing the foundation for real-time audio processing and advanced conversational capabilities, particularly tailored to the restaurant industry. You will design and evaluate algorithms to enhance speech and audio performance in our products. Working closely with product and engineering teams, you will develop and assess new solutions, devising innovative ways to integrate them. Additionally, you will prototype and research various software/hardware solutions involving audio, speech, speakers, and sensors for phone and drive-through interfaces. 100% remote Salary range $140,000 - $220,000 Essential Job Functions Algorithm Development: Create, design, and troubleshoot real-time audio algorithms. Collaborative Engineering: Work within a multidisciplinary team to make essential architectural decisions for efficient software delivery. Software Creation: Develop software for various consumer devices with real-time audio inputs and outputs. Code Quality: Write clean, readable code, efficiently debug complex issues, and prioritize tasks to maintain high productivity. Continuous Learning: Engage in ongoing learning, explore new technologies, and stay updated on the latest audio and digital signal processing advancements. AI/ML Integration: Utilize AI/ML techniques for speech enhancement. Prototyping: Rapidly prototype new software and hardware solutions to contribute to product ideation and development. Master’s or PHD or multiple years of industry experience in computer science or engineering. Experience evaluating speech quality/recognition and building scalable systems for real-time audio input/output across multiple concurrent channels. Good understanding of voice activity detection (VAD), beamforming, source separation, and speaker diarization/separation. Interest in prototyping hardware solutions ranging from hobby to professional levels, and a strong sense of future-proofing regarding hardware decisions. Good problem-solving skills and ability to work independently and in a team. Understanding of conversational English and experience with voice programs/products. Strong communication skills for explaining technical ideas to various audiences. Ability to manage product specifications from concept to production. Extensive experience ordering food at fast food and quick service restaurants. 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