Tech Lead, Payments

Chalkboard•New York, NY

About The Position

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. We’re looking for a Tech Lead, Payments to join Chalkboard and take technical ownership of one of the most critical systems in the business. This is a principal-level, 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

Requirements

~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
Experience working in both startup and larger company settings
Comfort processing and reasoning about hundreds of thousands of daily payment transactions

Nice To Haves

Direct experience with payments providers or complex financial integrations
Sports betting or gaming industry background
Prior ownership of mission-critical, revenue-impacting systems

Responsibilities

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
Reduce operational and communication friction caused by time zone differences with offshore teams
Act as the primary technical point of contact for payment partners (e.g., NewWay, AeroPay, Pushcash, and future providers)
Lead recurring syncs with payment providers to ensure system health and alignment
Coach and support engineers on the payments pod through strong technical leadership
Partner closely with Product Managers to align technical decisions with business priorities
Navigate startup ambiguity and move quickly without perfect information
Identify risks, gaps, and improvement opportunities in payment architecture and processes
Make clear technical decisions and move forward confidently, rather than waiting for consensus
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
Raise the bar for technical decision-making and ownership across the payments domain

Benefits

Employee Sponsored medical, dental, & vision coverage starting within 30 days. We cover 80% for employees and 70% for dependents.
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

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