Checkmate

• Onboarding & Activation • Lead onboarding for new brands, from kickoff through go-live • Configure each brand's offers, channels, and audiences for their goals • Set success metrics and a clear first-30-days plan with every brand • Get brands to first revenue quickly and cleanly • Account Management • Own a book of brands as their main point of contact • Run regular check-ins, business reviews, and performance recaps • Track account health, usage, and renewal timelines • Get ahead of risk before it reaches a renewal • Retention & Growth • Own renewals across your book • Identify expansion opportunities and build the case with data • Turn strong results into case studies and references • Cross-Functional Execution • Work with Rev Ops to translate performance into account actions • Bring brand feedback to Product and Ops, and flag what matters • Partner with Sales on clean handoffs and account planning • Build for Scale • Help standardize onboarding playbooks and account templates • Improve CS workflows and reduce manual steps • Contribute to repeatable processes as the team grows • Why This Role MattersBrands come to Checkmate for incremental revenue. You're the person who makes sure they get it, and that they stay to get more. When your brands are live, growing, and renewing, the whole business compounds. This is one of the most direct lines to revenue we have, and it's yours to own.

Role Description We're hiring a Customer Success Manager to own our brand relationships from the first day of onboarding through renewal and expansion. You'll be the person brands trust to make Checkmate work for them: live fast, revenue early, and strong first results that turn into long-term partnerships. This is a high-ownership role on a small team. You'll carry your own book of brands, run those relationships end to end, and sit close to the revenue we deliver. If you like owning outcomes, moving fast, and being the reason a brand stays and grows, you'll thrive here. What You’ll Do - Onboarding & Activation - Lead onboarding for new brands, from kickoff through go-live - Configure each brand's offers, channels, and audiences for their goals - Set success metrics and a clear first-30-days plan with every brand - Get brands to first revenue quickly and cleanly - Account Management - Own a book of brands as their main point of contact - Run regular check-ins, business reviews, and performance recaps - Track account health, usage, and renewal timelines - Get ahead of risk before it reaches a renewal - Retention & Growth - Own renewals across your book - Identify expansion opportunities and build the case with data - Turn strong results into case studies and references - Cross-Functional Execution - Work with Rev Ops to translate performance into account actions - Bring brand feedback to Product and Ops, and flag what matters - Partner with Sales on clean handoffs and account planning - Build for Scale - Help standardize onboarding playbooks and account templates - Improve CS workflows and reduce manual steps - Contribute to repeatable processes as the team grows Who You Are - You build trust fast, and people want to keep working with you - You're energized by ownership and comfortable being the single point of accountability for an account - You read the data, find the story in it, and turn it into a recommendation a brand will act on - You stay organized and move fast when you're juggling a lot at once - You're genuinely curious about ecommerce and what makes brands grow What You Bring - 3+ years in customer success, account management, or partnerships, ideally in martech, ecommerce, or SaaS - A track record of retaining and growing a book of business - Comfort with performance data and the ability to turn metrics into a clear narrative - Sharp communication, whether you're running a business review or writing a follow-up - Bonus: you already know the DTC stack (Klaviyo, Attentive, Shopify) or have worked with DTC brands Why Join Checkmate - Solve real problems: Help DTC brands unlock millions in missed revenue - Work with top brands: Partner with category leaders like Brooklinen, Quay, and ColourPop - Growth opportunity: Exposure to AI, martech innovation, and fast-moving eCommerce Compensation & Benefits - Competitive base salary + commission package - Equity in a fast-growing, venture-backed company - Traditional medical/dental/vision/other healthcare coverage - 4 weeks PTO + health days - 401k plan - Monthly gym membership reimbursement - Company retreats and team get togethers - Remote-first culture (preference for those near major cities - NYC, LA, SLC, Miami, Chicago, etc.)

Role Description An Onboarding Specialist ensures a smooth transition for new clients and locations as they adopt new products or systems. This is done by developing a deep understanding of our internal products and processes and maintaining solid relationships with internal and external stakeholders. - Onboarding: Onboard location(s) for different brands for diverse products assigned. - Vertical-Specific Expertise: Develop deep knowledge and expertise in diverse onboarding processes, such as point-of-sale (POS) systems, third-party integrations, direct ordering systems, etc. - Testing and Validation: Conduct testing to ensure the system or product functions correctly and meets the specified requirements. Validate that all components are working as expected before full deployment. - Client Communication: Communicate with clients when needed via email or phone to discuss onboarding requirements. - Collaborative Projects: Collaborate with internal and/or external teams to find solutions, ensuring that customer’s onboarding problems are resolved comprehensively. - Documentation: Create and maintain brand-specific documentation to ensure successful onboarding based on brand requirements. - Managing Work Queues: Monitoring and prioritizing tasks assigned to ensure timely completion. Qualifications - Bachelor's degree or equivalent job experience of at least 3+ years in client operations and relationships. - Excellent communication and interpersonal skills with the ability to engage effectively with clients and internal teams. - Superior organizational and time management skills, with a capacity to handle multiple high-priority projects simultaneously. - Strong attention to detail ensures that all onboarding process aspects are executed flawlessly. - Ability to adapt to changing environments and manage multiple priorities in a fast-paced setting.

Role Description Checkmate is recruiting for a Senior Full Stack Engineer to join our Engineering team helping to engineer, operate, and grow our unique web-based restaurant-tech SaaS platform using AI technologies. In this role you will partner closely with our Product team and other Engineering team members to drive innovative new features, software improvements, and architectural agility supporting our product roadmap within our product-led Engineering organization that services both internal and external customers. This role is ideal for a senior level engineer who has experience leading other team members designing and coding on enterprise level Python applications, and someone who is comfortable breaking down complex problems into iterative deliverables using advancements in AI to ship faster. Additionally, Checkmate is a 100% remote based and globally distributed organization! On the Checkmate Engineering Team you’ll have the opportunity to use cutting edge technologies in an AI-led SDLC environment to lead initiatives that grow, modernize, and scale core parts of our product platform. You’ll own features end-to-end, drive architectural improvements, and help elevate the technical bar across the team. Essential Job Functions - Full Stack Development: - Collaborate with Product, Design, and Engineering teams to design, build, test, deploy, and maintain scalable web applications - Leverage AI coding agents to accelerate product development and defect resolution - Develop and maintain RESTful and/or GraphQL APIs - Develop asynchronous application processing using tools like Sidekiq - Build and maintain responsive, high-performance React.js interfaces and reusable components - Write and optimize SQL queries across PostgreSQL/MySQL databases - Architecture and Design: - Improve application reliability, scalability, and long-term maintainability of large enterprise systems - Create, and collaborate with other engineers on, technical specifications aligned against short term and long term Product roadmaps and enterprise architectural goals - Use APM and observability tools to detect, diagnose, and fix performance bottlenecks - Identify technical debt and drive practical solutions to pay down debt - End-to-End Feature Ownership: - Own features and complex issues from product design through development, deployment, and monitoring. - Participate in all parts of the Product, Design, and Engineering processes building new features together in a collaborative pod-based environment - Interact with our internal customers using your contributions to our software platform in support of our external customers - Leadership Opportunities: - Work with team members to identify, prioritize, and reduce technical debt and improve scalability and performance across the codebase - Participate in architecture and technical design discussions across Product and Engineering - Contribute to peer code reviews, automated testing, CI/CD pipelines, and deployment workflows - Investigate and resolve outages with root-cause analysis and clear follow-up improvements - Mentor junior engineers and promote engineering best practices using AI-led practices Qualifications - Bachelor’s degree in Computer Science, Engineering, or equivalent practical experience Requirements - 8+ years of experience building enterprise level applications using Python - 3+ years working with React.js or a related modern javascript frameworks - 3+ years working within a 30+ team member sized engineering team - 3+ years working 100% remote and a desire to continue working remotely - 3+ years developing and operating applications on AWS - 2+ years developing using AI coding agents including Claude Code or Codex Technical Skill Requirements - Experience working using Docker locally - Experience running enterprise level production workload apps on AWS - Experience integrating with RESTful and GraphQL APIs - Experience writing raw SQL queries in a relational database - Experience building asynchronous background job processes across multiple tools/frameworks - Experience with observability tools like Datadog, Sentry, or New Relic - Experience writing automated unit tests having > 60% code coverage - CI/CD development experience creating Github Actions - Experience modernizing legacy Python applications Team and Work Style Requirements - Experience working in product led engineering organization - Experience working in a multi-team / pod-based engineering team - Works with an accountability and ownership mindset and calls out gaps where they exist - Experience working in high-volume transactional production environments - Exceptional at translating product requirement documents into detailed technical specifications - Work US Eastern Timezone hours between 9am - 5pm ET

Role Description Checkmate is recruiting for a Senior Full Stack Engineer to join our Engineering team helping to engineer, operate, and grow our unique web-based restaurant-tech SaaS platform using AI technologies. In this role you will partner closely with our Product team and other Engineering team members to drive innovative new features, software improvements, and architectural agility supporting our product roadmap within our product-led Engineering organization that services both internal and external customers. This role is ideal for a senior level engineer who has experience leading other team members designing and coding on enterprise level Ruby on Rails applications, and someone who is comfortable breaking down complex problems into iterative deliverables using advancements in AI to ship faster. Additionally, Checkmate is a 100% remote based and globally distributed organization! On the Checkmate Engineering Team you’ll have the opportunity to use cutting edge technologies in an AI-led SDLC environment to lead initiatives that grow, modernize, and scale core parts of our product platform. You’ll own features end-to-end, drive architectural improvements, and help elevate the technical bar across the team. Essential Job Functions - Full Stack Development: - Collaborate with Product, Design, and Engineering teams to design, build, test, deploy, and maintain scalable web applications - Leverage AI coding agents to accelerate product development and defect resolution - Develop and maintain RESTful and/or GraphQL APIs - Develop asynchronous application processing using tools like Sidekiq - Build and maintain responsive, high-performance React.js interfaces and reusable components - Write and optimize SQL queries across PostgreSQL/MySQL databases - Architecture and Design: - Improve application reliability, scalability, and long-term maintainability of large enterprise systems - Create, and collaborate with other engineers on, technical specifications aligned against short term and long term Product roadmaps and enterprise architectural goals - Use APM and observability tools to detect, diagnose, and fix performance bottlenecks - Identify technical debt and drive practical solutions to pay down debt - End-to-End Feature Ownership: - Own features and complex issues from product design through development, deployment, and monitoring. - Participate in all parts of the Product, Design, and Engineering processes building new features together in a collaborative pod-based environment - Interact with our internal customers using your contributions to our software platform in support of our external customers - Leadership Opportunities: - Work with team members to identify, prioritize, and reduce technical debt and improve scalability and performance across the codebase - Participate in architecture and technical design discussions across Product and Engineering - Contribute to peer code reviews, automated testing, CI/CD pipelines, and deployment workflows - Investigate and resolve outages with root-cause analysis and clear follow-up improvements - Mentor junior engineers and promote engineering best practices using AI-led practices Qualifications - Bachelor’s degree in Computer Science, Engineering, or equivalent practical experience Requirements - 6+ years of experience building enterprise level applications using Ruby on Rails - 3+ years working with React.js or a related modern javascript frameworks - 3+ years working within a 30+ team member sized engineering team - 3+ years working 100% remote and a desire to continue working remotely - 3+ years developing and operating applications on AWS - 2+ years developing using AI coding agents including Claude Code or Codex Technical Skill Requirements - Experience working using Docker locally - Experience running enterprise level production workload apps on AWS - Experience integrating with RESTful and GraphQL APIs - Experience writing raw SQL queries in a relational database - Experience building asynchronous background job processes across multiple tools/frameworks - Experience with observability tools like Datadog, Sentry, or New Relic - Experience writing automated unit tests having > 60% code coverage - CI/CD development experience creating Github Actions - Experience modernizing legacy Ruby on Rails applications Team and Work Style Requirements - Experience working in product led engineering organization - Experience working in a multi-team / pod-based engineering team - Works with an accountability and ownership mindset and calls out gaps where they exist - Experience working in high-volume transactional production environments - Exceptional at translating product requirement documents into detailed technical specifications - Work US Eastern Timezone hours between 9am - 5pm ET

Role Description We are hiring Operations/Phone Specialist for our Customer Support departments. What we do as a business is we provide “solutions” to our customers. This solution is a combination of “technology” plus “service”. The company has the technology but we are looking for someone very service oriented and a problem solver. These are large clients we work with, so we are looking for someone who can create a relationship with the clients, understand their needs and provide a “solution”. Every client says they are different, but they are more similar than they realize. We have the unique opportunity to look at the same problem across the industry, find the best practice and solution and recommend that to our clients. What we offer today is a necessity, a need. We as a company are in an extremely fortunate position to be in the right position at the right time, and we have more clients than we can handle. So this person should be able to realize that, and handle the clients accordingly. The solution we provide will immensely improve our customer’s operations, we just have to be able to explain it clearly and succinctly. There is always more than one way to solve a problem. Looking for someone who can take initiative, think creatively and use the various resources at their disposal to solve problems. The ability to clearly communicate, both verbally and written, is a requirement. What we value above all is diligence. We have an excellent team and if we see you putting in your 100%, the rest of the team will go out of its way to lift you up until you are in a position where you are helping others. Responsibilities - Manage large amounts of inbound and outbound calls in a timely manner - Follow communication “scripts” when handling different topics - Greet customers warmly and ascertain problem or reason for calling - Identify customers’ needs, clarify information, research every issue and provide solutions and/or alternatives - Build sustainable relationships and engage customers by taking the extra mile - Provide accurate, valid and complete information by using the right methods/tools - Frequently attend educational seminars to improve knowledge and performance level - Suggest solutions when a product malfunctions - Attempt to persuade customer to reconsider cancellation - Resolve product or service problems by clarifying the customer's complaint; determining the cause of the problem; selecting and explaining the best solution - Meet personal/team qualitative and quantitative targets Qualifications - 3+ years of experience with strong phone and verbal communication skills, along with active listening - Ready to work on India Night shifts - International calling experience must (Preferably US) - Familiarity with CRM systems and practices - Customer focus and adaptability to different personality types - Ability to multi-task, set priorities and manage time effectively - Graduate, in any stream - Excellent communication skills – both verbal and written - Business acumen with a problem-solving attitude - Someone who thrives in a very fast-paced, quickly evolving environment - Comfortable to working in the US shift hours Benefits - Competitive salary - Awesome work environment at a company with a huge vision

• Build Strategic Partnerships • Target high-growth Shopify merchants ($10M–$500M GMV) in fashion, beauty, and home verticals • Conduct deep discovery to understand growth challenges, constraints, and team priorities • Present data-driven business cases showing projected ROAS, incremental revenue, and payback periods • Navigate complex buying committees involving Growth, Marketing, RevOps, and Finance stakeholders • Establish yourself as a trusted advisor—not just a vendor • Drive Revenue • Own a quota and manage full-cycle sales from prospecting to close • Build pipeline through outbound prospecting, agency partnerships, and ecosystem relationships • Maintain disciplined pipeline management and forecasting in Hubspot • Support onboarding and identify expansion opportunities based on performance data • Shape the Playbook • Contribute product feedback based on real customer needs and market gaps • Help refine our GTM strategy as we scale into new verticals and use cases • Collaborate with Product, Marketing, and Customer Success to improve the customer journey • Be a founding member of our sales organization—what you build here will scale

**The Role 💼**This isn't a traditional AE role. You'll function as a strategic growth advisor who also carries quota. Focusing on the fashion, beauty, and home verticals, you'll identify brands in our ICP, diagnose their conversion problems, prescribe compelling solutions with Checkmate's product offerings, build trusted partnerships with DTC growth teams, and then close those relationships. **What You’ll Do** ⚡ - **Build Strategic Partnerships** - Target high-growth Shopify merchants ($10M–$500M GMV) in fashion, beauty, and home verticals - Conduct deep discovery to understand growth challenges, constraints, and team priorities - Present data-driven business cases showing projected ROAS, incremental revenue, and payback periods - Navigate complex buying committees involving Growth, Marketing, RevOps, and Finance stakeholders - Establish yourself as a trusted advisor—not just a vendor - **Drive Revenue** - Own a quota and manage full-cycle sales from prospecting to close - Build pipeline through outbound prospecting, agency partnerships, and ecosystem relationships - Maintain disciplined pipeline management and forecasting in Hubspot - Support onboarding and identify expansion opportunities based on performance data - **Shape the Playbook** - Contribute product feedback based on real customer needs and market gaps - Help refine our GTM strategy as we scale into new verticals and use cases - Collaborate with Product, Marketing, and Customer Success to improve the customer journey - Be a founding member of our sales organization—what you build here will scale

The Problem We’re Solving 🎯 Most DTC brands are leaving revenue on the table. They spend millions acquiring customers through paid channels, then lose 60%+ of high-intent shoppers to cart abandonment, anonymous browsing, and missed retargeting opportunities. The issue isn't traffic—it's conversion architecture. Brands lack the infrastructure to capture intent signals, recognize returning visitors, and re-engage shoppers at the moments that matter most. That's where Checkmate comes in. Our AI-powered platform captures shopping intent from 100M+ shoppers across the web—wishlists, carts, browsing sessions—and turns it into high-converting campaigns that consistently deliver revenue uplift in 30 days. But here's the thing: selling this solution requires more than a good pitch deck. It requires someone who can walk into a growth team's meeting, diagnose where they're leaving money on the table, and prescribe a strategic path forward. About Checkmate 🛍 📲 Checkmate is an AI marketing platform that helps DTC brands capture anonymous shoppers, launch targeted campaigns, and drive measurable revenue. Our platform uses AI to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns that engage the 100M+ high-intent shoppers in our network. We offer three core products for brands: - Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows. - Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS. - Audiences: Capture pre-checkout emails via gated discounts and gain competitive insights. We work with leading DTC brands like Stanley, Quay, ColourPop, Laneige, and Dockers. Backed by Google Ventures, Fuel Capital, and others. The Role 💼 This isn't a traditional AE role. You'll function as a strategic growth advisor who also carries quota. Focusing on the fashion, beauty, and home verticals, you'll identify brands in our ICP, diagnose their conversion problems, prescribe compelling solutions with Checkmate's product offerings, build trusted partnerships with DTC growth teams, and then close those relationships. What You’ll Do ⚡ - Build Strategic Partnerships - Target high-growth Shopify merchants ($10M–$500M GMV) in fashion, beauty, and home verticals - Conduct deep discovery to understand growth challenges, constraints, and team priorities - Present data-driven business cases showing projected ROAS, incremental revenue, and payback periods - Navigate complex buying committees involving Growth, Marketing, RevOps, and Finance stakeholders - Establish yourself as a trusted advisor—not just a vendor - Drive Revenue - Own a quota and manage full-cycle sales from prospecting to close - Build pipeline through outbound prospecting, agency partnerships, and ecosystem relationships - Maintain disciplined pipeline management and forecasting in Hubspot - Support onboarding and identify expansion opportunities based on performance data - Shape the Playbook - Contribute product feedback based on real customer needs and market gaps - Help refine our GTM strategy as we scale into new verticals and use cases - Collaborate with Product, Marketing, and Customer Success to improve the customer journey - Be a founding member of our sales organization—what you build here will scale

The Problem We’re Solving 🎯 Most DTC brands are leaving revenue on the table. They spend millions acquiring customers through paid channels, then lose 60%+ of high-intent shoppers to cart abandonment, anonymous browsing, and missed retargeting opportunities. The issue isn't traffic—it's conversion architecture. Brands lack the infrastructure to capture intent signals, recognize returning visitors, and re-engage shoppers at the moments that matter most. That's where Checkmate comes in. Our AI-powered platform captures shopping intent from 100M+ shoppers across the web—wishlists, carts, browsing sessions—and turns it into high-converting campaigns that consistently deliver revenue uplift in 30 days. But here's the thing: selling this solution requires more than a good pitch deck. It requires someone who can walk into a growth team's meeting, diagnose where they're leaving money on the table, and prescribe a strategic path forward. About Checkmate 🛍 📲 Checkmate is an AI marketing platform that helps DTC brands capture anonymous shoppers, launch targeted campaigns, and drive measurable revenue. Our platform uses AI to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns that engage the 100M+ high-intent shoppers in our network. We offer three core products for brands: - Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows. - Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS. - Audiences: Capture pre-checkout emails via gated discounts and gain competitive insights. We work with leading DTC brands like Stanley, Quay, ColourPop, Laneige, and Dockers. Backed by Google Ventures, Fuel Capital, and others. The Role 💼 This isn't a traditional AE role. You'll function as a strategic growth advisor who also carries quota. Focusing on the fashion, beauty, and home verticals, you'll identify brands in our ICP, diagnose their conversion problems, prescribe compelling solutions with Checkmate's product offerings, build trusted partnerships with DTC growth teams, and then close those relationships. What You’ll Do ⚡ - Build Strategic Partnerships - Target high-growth Shopify merchants ($10M–$500M GMV) in fashion, beauty, and home verticals - Conduct deep discovery to understand growth challenges, constraints, and team priorities - Present data-driven business cases showing projected ROAS, incremental revenue, and payback periods - Navigate complex buying committees involving Growth, Marketing, RevOps, and Finance stakeholders - Establish yourself as a trusted advisor—not just a vendor - Drive Revenue - Own a quota and manage full-cycle sales from prospecting to close - Build pipeline through outbound prospecting, agency partnerships, and ecosystem relationships - Maintain disciplined pipeline management and forecasting in Hubspot - Support onboarding and identify expansion opportunities based on performance data - Shape the Playbook - Contribute product feedback based on real customer needs and market gaps - Help refine our GTM strategy as we scale into new verticals and use cases - Collaborate with Product, Marketing, and Customer Success to improve the customer journey - Be a founding member of our sales organization—what you build here will scale