Lead Software Engineer at Chalkboard

About Chalkboard: Chalkboard is building the future of sports gaming. Our mission is to blur the line between watching and playing by turning real-money sports gaming into a social, immersive experience built for fans who play to win. We're not just creating another betting app. We're reimagining how sports fans engage with the games they love. At our core, we’re a team of sports-obsessed builders who value clarity, fairness, and the thrill of helping fans turn insight into action. The Role: We’re looking for a Lead Software Engineer to join Chalkboard and take technical ownership of one of the most critical systems in the business. This is a highly technical role responsible for the reliability, scalability, and evolution of our payments platform. You’ll act as the technical authority for payments, owning architecture, integrations, security, and performance all while partnering closely with Product, RevOps, and Engineering leadership. If you thrive in complex, high-stakes systems and enjoy leading through deep technical expertise, this role is for you Your Game Plan: You’ll take ownership of Chalkboard’s payments platform, improving reliability, scalability, and security while leading integrations with current and future payment partners. - Take end-to-end technical ownership of Chalkboard’s payments systems and integrations - Improve payment flows, system architecture, and security posture across the platform Scale payment processing from current volumes (~250k daily transactions) toward significantly higher throughput - Evaluate, implement, and onboard new payment providers and integrations - Act as the primary technical point of contact for payment partners (e.g., NewWay, AeroPay, Pushcash, and future providers) - Partner closely with Product Managers to align technical decisions with business priorities - Identify risks, gaps, and improvement opportunities in payment architecture and processes - Build systems that are resilient, observable, and easy to evolve - Establish clear, durable technical documentation where little exists today - Build trust quickly with Product and RevOps by delivering reliable outcomes What You Bring to the Team: - ~8+ years of experience across backend and frontend engineering - Microservices architecture experience - Full stack experience with Node.js, React.js, React Native, PostgreSQL, MongoDB, and GCP - Deep understanding of databases, system design, and large-scale data processing - Proven experience building and operating high-volume payment systems Background in fintech and/or sports betting environments - Comfort processing and reasoning about hundreds of thousands of daily payment transactions Pro Points: - Direct experience with payments providers or complex financial integrations - Sports betting or gaming industry background - Prior ownership of mission-critical, revenue-impacting systems Why Chalkboard: We care about results, but also how we get there. Our core tenets aren’t slogans here, they’re how we operate. As Chalkboard grows, so do you. New problems, bigger plays, and opportunities to step up when it matters most happen often here. We want our team performing at their best, so here’s how we support our players: - Comprehensive medical, dental, and vision coverage starting within 30 days, with the majority of premiums covered by Chalkboard - 401(k) with company match - Lunch on us everyday with a corporate DoorDash account - Refuel in the office with protein shakes, energy drinks, and a snack buffet - Flexible time off policy, plus 10 company holidays, WFH during the holidays