VP of Product Engineering 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 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 VP of Product Engineering to lead one of our core engineering domains and scale a high-performing team. This is a people-first leadership role with strong technical depth. You’ll guide execution, elevate engineering quality, and ensure your team consistently delivers reliable, high-impact product experiences. In this role, you’ll partner closely with our VP of Technical Engineering, Product, Design, Data, and QA to shape roadmaps, define technical direction, and ship features that power how fans experience sports in real time. If you love building teams, care deeply about system design and engineering excellence, and thrive in fast-moving environments, this is your opportunity to lead from the front. Your Game Plan: Lead, coach, and scale a high-performing engineering team while driving predictable, high-quality execution across mobile and backend systems. You’ll raise the bar on technical excellence, delivery rigor, and cross-functional alignment as we continue to grow. - Lead, coach, and develop a team of backend, mobile, and/or full-stack engineers - Drive weekly team alignment through sprint planning, prioritization, retros, and reviews - Partner with Product to define roadmaps, scopes, trade-offs, and delivery expectations - Ensure the team ships high-quality features on predictable timelines - Improve team productivity through better process, tooling, and communication - Elevate standards across architecture, testing, reliability, and code quality - Conduct meaningful 1:1s, performance reviews, and career development conversations. - Run design reviews and RFC discussions, providing strong technical guidance - Hire, onboard, and retain exceptional engineering talent - Make clear decisions and manage trade-offs across technical and business constraints - Own service reliability, system performance, and engineering accountability - Collaborate cross-functionally with Product, Design, QA, Data, and DevOps - Maintain strong relationships with stakeholders and set transparent expectations - Foster a culture of trust, ownership, feedback, and continuous improvement - Partner tightly with Product while serving as the technical owner of your domain What You Bring to the Team: - 8+ years of software engineering experience - 2–4+ years managing engineering teams - Strong background in backend, mobile, or full-stack development - Experience shipping and operating real-world consumer products - Deep understanding of system design, scalability, and reliability - Track record of improving engineering processes and team performance - Excellent communication and leadership skills - Ability to create clarity, make decisions quickly, and lead through ambiguity Pro Points: - Experience in gaming, fintech, real-time data systems, or high-scale consumer apps - Familiarity with mobile analytics, event tracking, and growth experimentation - Experience with observability tooling (Datadog, Sentry, OpenTelemetry) - Exposure to data engineering or pipeline-driven products Why Chalkboard: We care about results, but also how we get there. 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 day 1, 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