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 Do Build & 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!

• Oversee the full customer payment lifecycle to ensure timely collection of incoming payments • Maintain accurate customer account records • Develop effective credit and collection strategies • Collaborate with internal stakeholders to optimize cash flow and minimize bad debt • Assist with new customer onboarding including, but not limited to, setting up payment profiles for new customers to establish a means of collecting payments • Process payments from clients and perform reconciliation between amounts invoiced and amounts paid • Monitor customer payment behaviors and autonomously flag at-risk accounts and developing high-risk situations to internal leadership • Collaborate with clients, finance and accounting to resolve billing disputes and customer inquiries • Manage communication with internal stakeholders and clients surrounding overdue payments • Perform customer credit evaluations and set credit limits as needed • Analyze receivables aging reports and prepare regular status reports for leadership • Drive process improvements to increase efficiency and accuracy in accounts receivable operations • Work with operations team members on internal cash flow and revenue recognition projects • Proactively iterate customer-facing messaging to ensure engagement

• Own and optimize HubSpot CRM architecture, including pipelines, lifecycle stages, routing logic, required fields, and workflows. • Establish and enforce standards for data hygiene, validation, deduplication, and field consistency across revenue systems. • Partner with the Data Team to integrate HubSpot with ActiveCampaign, Zendesk, Stripe, Superset, and product usage data. • Maintain a single source of truth for revenue data from lead acquisition through expansion. • Serve as the centralized owner of discounting, deal guardrails, and approval workflows. • Define and enforce pricing rules and discount thresholds for Sales and Customer Success. • Ensure visibility into deal approvals, exceptions, and margins to protect revenue integrity. • Collaborate with Finance and Revenue Leadership to align pricing execution with financial targets. • Build and manage commission logic, automation, and payout processes, primarily within HubSpot. • Ensure commission calculations are accurate, timely, and transparent across Sales and Customer Success. • Partner with Finance on monthly reconciliation and auditability. • Support compensation plan updates and annual performance cycles. • Develop dashboards and models tracking pipeline health, sales velocity, win rates, CAC payback, and ARR/MRR. • Partner with Sales and Marketing leaders to maintain accurate, data-driven forecasting cadences. • Deliver monthly insights on performance trends, risks, and opportunities. • Build “what-if” models to assess the impact of pricing changes, churn, or funnel improvements. • Automate workflows across the funnel to reduce manual effort and lead leakage. • Define and refine MQL, SQL, and PQL criteria in partnership with Growth and Sales. • Drive operational clarity and accountability across Marketing, Sales, Customer Success, and Finance. • Build scalable processes that support larger deals and longer sales cycles.

• Review incoming deals for pricing accuracy, margin thresholds, and discount compliance • Serve as the first checkpoint between Sales and Finance on non-standard deal terms • Manage the deal approval workflow — routing requests, tracking status, and keeping deals from stalling • Build and maintain dashboards that give sales leadership and executives real-time visibility into pipeline health • Collaborate with Sales, Finance, and Engineering to gather inputs needed for accurate pricing • Design reports and dashboards and perform ad-hoc analysis as needed