Vice President of Technology, Overtime

• 10+ years in technology, with at least 5 years leading both infrastructure/IT and software engineering teams
• Demonstrated ownership of an annual technology budget, including vendor negotiation, procurement, and forecasting alongside Finance
• Deep hands-on experience with cloud infrastructure (AWS preferred), CI/CD, networking, identity, and endpoint management
• Track record running a security program, including endpoint protection, access governance, security awareness training, and incident response
• Experience leading engineering delivery for consumer-facing products at scale, including mobile and web
• Comfort operating in a live events or broadcast environment
• Strong written and verbal communication, with a proven ability to make technical trade-offs legible to executive and business stakeholders

Desirable

• Overtime is looking for a Vice President of Technology to own both halves of the technology function: the IT and infrastructure that the company runs on, as well as the software engineering organization that builds and operates our consumer products, internal platforms, and live game-day systems across Overtime, OTE, OT7, and OT Select
• This is a hands-on leadership role. The person in it sets technical direction, owns the budget, runs the security and compliance program, and leads the engineers who ship the apps, websites, storefront, and data pipelines that our audience and our leagues depend on. Overtime is a hybrid company working 3+ days a week in our DUMBO office in Brooklyn
• Develop, execute, and own a comprehensive IT strategy and roadmap in partnership with leadership, providing technology leadership and driving digital transformation initiatives that support business growth
• Manage the annual IT budget (OpEx/CapEx) in collaboration with the VP of Finance, ensuring cost-effective procurement, transparent reporting, and maximum ROI on technology investments
• Oversee all IT operations and infrastructure, ensuring the stability, security, and high availability of networks, servers, cloud environments, and end-user computing
• Manage the lifecycle of core business applications, including selection, implementation, integration, and support, to ensure they meet evolving business needs
• Identify and deploy AI and automation solutions to enhance productivity and decision-making
• Lead the enterprise-wide cybersecurity program, including threat management, incident response, security awareness training, and the development of policies to protect company data and assets
• Ensure IT compliance with all legal and regulatory requirements, establish IT governance policies, and manage risk through regular audits and assessments
• Build and lead the in-house IT function, fostering a high-performance, customer-centric culture and effectively communicating technical concepts to all business stakeholders
• Own the media supply chain, from asset management and storage gateways through transcode, automated QC, and AI-assisted metadata enrichment, partnering with Content and Production on throughput and quality
• Own the software engineering function end to end, covering consumer mobile apps, web properties, the Overtime Shop storefront, internal admin tools, and the platform services behind them, and set the standards for how work is scoped, tracked, reviewed, and released
• Own the cloud platform and production reliability across our AWS estate, including Kubernetes, EC2, Amplify, serverless jobs, and managed databases, with clear deploy patterns, branch protection, access controls, and a working incident response practice
• Own live game-day technology for OTE, OT7, and OT Select, including the statistics pipeline that feeds broadcast graphics and web, pre-game readiness checks, and real-time escalation during events
• Translate business and product priorities into a sequenced engineering roadmap, balancing new product work against reliability, platform, and technical debt investment, and communicate trade-offs plainly to non-technical stakeholders
• Establish and maintain engineering documentation, runbooks, and architectural records
• Evaluate and manage engineering vendors, platforms, and build-versus-buy decisions, including contract negotiation and renewal in partnership with Finance and Legal