Lead Software Engineer, Operations

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 Tech Lead, Operations to join Chalkboard and help us scale the internal systems that power our day-to-day business. This role sits at a principal-level impact and is critical to reducing operational friction across Customer Support, RevOps, Marketing, and Product. In this role, you'll work cross-functionally, not just with Engineering, playing a meaningful part in how internal teams deliver promos, support users, and operate efficiently in real time. If you love building from scratch, automating messy workflows, and bringing order to chaos in fast-moving environments, this role is for you. Your Game Plan: You'll own the technical foundation that supports Chalkboard's internal operations, with a focus on automation, tooling, and documentation. Level Up Our Game: Deeply understand Chalkboard's operational workflows across Customer Support, RevOps, Marketing, and Product Identify high-leverage opportunities to eliminate manual work through automation Centralize fragmented operational workflows into the admin panel and internal tooling Build and evolve tooling for promo delivery, push notifications, and internal integrations Partner closely with RevOps to support daily promo execution and operational needs Play Like a Captain: Lead without direct authority by earning trust across CS and RevOps teams Create documentation processes from scratch and drive adoption across the org Establish clarity in areas that are currently messy, undocumented, or ambiguous Serve as a technical thought partner for non-engineering stakeholders Find a Way to Win: Make progress even when context is incomplete or requirements are evolving Navigate cross-functional priorities while balancing speed and quality Improve operational reliability without slowing down the business We Are Better Together: Act as a connective tissue between Engineering and operational teams Help teammates leverage internal systems more effectively Raise the bar for how Chalkboard builds and maintains internal tools What You Bring to the Team: Strong backend engineering experience, with comfort owning systems end-to-end Microservices architecture experience Full stack experience with Node.js, React.js, React Native, PostgreSQL, MongoDB, and GCP Proven ability to automate operational workflows and internal processes Experience partnering closely with non-engineering teams (CS, RevOps, Marketing) Track record of building internal tools, admin panels, or operational platforms Ability to create and maintain clear documentation in low-documentation environments Comfort operating at a principal-level scope with high autonomy and accountability Pro Points: Python experience, particularly in risk or operations-focused microservices Experience integrating third-party tools (e.g., Intercom-like systems) into internal platforms Background supporting high-velocity operational teams Why Chalkboard: We care about results, but also how we get there. Our core tenants 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: 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 Chalkboard is an equal opportunity employer: We celebrate diversity and are committed to creating an inclusive environment for all employees. Chalkboard does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other legally protected status. Work Authorization: We welcome applicants who are currently authorized to work in the United States. At this time, we're unable to provide visa sponsorship for this role.

Created: 2026-03-10