VP of Product Engineering

Chalkboard • New York, NY

23h • Hybrid

About The Position

Chalkboard is building the future of sports gaming, aiming to transform real-money sports gaming into a social, immersive experience for fans who play to win. The company focuses on reimagining how sports fans engage with games, driven by a team of sports-obsessed builders who value clarity, fairness, and helping fans turn insight into action. The role of VP of Product Engineering involves leading one of Chalkboard's core engineering domains and scaling a high-performing team. This is a people-first leadership position requiring strong technical depth. The VP will guide execution, elevate engineering quality, and ensure the team consistently delivers reliable, high-impact product experiences. The role requires close partnership with the VP of Technical Engineering, Product, Design, Data, and QA to shape roadmaps, define technical direction, and ship features that power real-time sports fan experiences. It's an opportunity for someone who enjoys building teams, cares deeply about system design and engineering excellence, and thrives in fast-moving environments.

Requirements

• 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

Nice To Haves

• 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

Responsibilities

• 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

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 1-10 employees