Lead Software Engineer, Payments

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, Payments & Internal Ops to join Chalkboard and take ownership of our payments ecosystem and internal operational systems. These are two of the most critical domains in our business and we must ensure they are scalable, secure, and built to support rapid growth.

In this role, you will partner closely with Product, Engineering, and Operations playing a critical part in how money moves through our platform and how internal teams operate at scale. You’ll act as the technical authority for payments, owning architecture, integrations, security, and performance. If you thrive in complex, high-stakes systems and enjoy leading through deep technical expertise, keep reading!

Your Game Plan:

You’ll take ownership of Chalkboard’s payments platform and internal tools, improving reliability, scalability, and security while leading integrations with current and future payment partners.

• Own and improve the performance, scalability, and reliability of our payments infrastructure, supporting high-volume transaction processing.

• Act as the technical leader for the pod, partnering closely with Product to shape roadmap and execution.

• Establish best practices in system design, security, and data integrity across payments and internal ops systems.

• Drive clarity through strong technical documentation and improved engineering processes.

• Serve as the primary point of contact for payment providers and internal stakeholders.

• Lead sprint planning, release coordination, and technical decision-making.

• Challenge assumptions and elevate engineering and product thinking with data-driven insights.

• Coach and support engineers while remaining hands-on in building and problem-solving.

• Improve team velocity, predictability, and execution through better planning and communication.

• Reduce operational friction across distributed teams and time zones.

• Identify gaps in systems, processes, and architecture—and take action to address them.

• Build strong partnerships across Product, Engineering, CS, RevOps, and Trading.

• Increase trust and collaboration between US-based and distributed engineering teams.

• Raise the bar for technical ownership and accountability across pods.

• Create shared understanding through documentation and cross-team communication.

What You Bring to the Team:

• ~8+ years of engineering experience with full-stack development

• Deep understanding of databases, system design, and large-scale data processing

• Full stack experience with Node.js, React.js, React Native, PostgreSQL, MongoDB, and GCP

• Proven experience building and operating high-volume payment systems

• Experience working in startup environments with an enterprise-level mindset

• Comfort processing and reasoning about hundreds of thousands of daily payment transactions

• Ability to operate as both a technical leader and product-minded engineer

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