Vice President of Technology

Overtime; Brooklyn (OH); Hybrid; USD 250,000 - 350,000; Full time

Job summary

Overtime seeks a hands-on Vice President of Technology to own IT, infrastructure, and software engineering across consumer products, platforms, and live game-day systems. The role combines strategic leadership with hands-on delivery in a hybrid environment from our DUMBO office in Brooklyn.

You will set technical direction, own the budget, run security/compliance, and lead engineers delivering apps, websites, storefronts, and data pipelines for Overtime, OTE, OT7, and OT Select.

Qualifications

• 10+ years in technology, with leadership experience across IT and software engineering teams.
• Experience owning budgets, security programs, and vendor negotiations.
• Background in live events, media, or entertainment environments is a plus.

Responsibilities

• Own IT and software engineering functions end-to-end, with clear roadmaps and governance.
• Lead cybersecurity program, incident response, and security awareness training.
• Oversee cloud platform, networks, and production reliability in AWS.
• Translate business needs into engineering priorities and roadmaps for multiple product lines.

Skills

Leadership

Technology strategy

Budget management

Cybersecurity program

Cloud infrastructure

AWS

CI/CD

Vendor management

Executive communication

Live events tech

Tools

Kubernetes

EC2

Amplify

Serverless

CI/CD

Job description

• 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

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