Head of AI Operations and Systems

Head of AI Operations & Systems

New York, NY | Full-Time | Onsite

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We are seeking a Head of AI Operations & Systems for a rapidly growing technology organization in New York City. This is a hands-on role for an operations leader who is comfortable working at the intersection of operations, AI, product, and technology.

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This individual will build and run scalable operating systems, implement AI-enabled tools and automation, and play a hands-on role in translating business and financial requirements into working, tested technology solutions. This is not a traditional strategy or oversight position. We are looking for someone who enjoys getting into the details, building systems, solving complex problems, and driving execution from concept through implementation.

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The Right Fit for This Role is an operator and builder. You can design an operating model at a high level, but you are equally comfortable opening the tools, examining the data, building a workflow, testing an output, identifying what isn't working, and driving the solution through completion. You don't simply develop AI strategies or manage technology projects. You understand how operational systems and technology actually get built and implemented, and you can demonstrate examples of what you have personally created, improved, tested, or delivered. This is an opportunity to have significant impact in a growing organization and help build its operating infrastructure from the ground up.

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What You'll Do

• Design and implement scalable operating processes and systems across a multi-location, multi-entity environment.
• Identify inefficient or manual workflows and improve them using AI, automation, and modern technology.
• Build and implement AI-enabled operational tools, including agentic workflows, custom GPTs, prompt-driven solutions, workflow automation, dashboards, and automated reporting.
• Develop KPIs, performance-monitoring systems, and analytics that provide leadership with real-time operational visibility.
• Translate operational and financial requirements into clear methodologies and business logic that can be implemented within technology platforms.
• Own structured build and release tracking, including backlog triage, ownership, priorities, dependencies, blockers, and escalations.
• Partner closely with Product and Technology to sequence technical work based on business priorities, dependencies, and deployment readiness.
• Maintain sufficient familiarity with GitHub/git-based development environments to understand repository activity, branches, commits, and build status.
• Personally test new functionality against defined acceptance criteria and help determine when solutions are truly ready for deployment.
• Create repeatable operating playbooks and processes that support growth and the integration of new business units or partners.
• Establish a strong operating cadence across leadership and cross-functional teams.
• Drive continuous improvement through experimentation, data, automation, and feedback loops.

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Skills and Experience  

• 7+ years of experience in AI/operations, technical program management, business operations, or a related operating role. Start up experience strongly preferred.
• Demonstrated experience building and standardizing operational systems in a complex or scaling organization.
• Strong hands-on AI fluency, including experience with agentic workflows, custom GPTs, prompt design, workflow automation, and systems integration.
• A track record of personally using technology to eliminate manual work and improve operational performance.
• Experience owning a structured backlog, issue-tracking, or build-governance process using tools such as Jira, Notion, Linear, or similar platforms.
• Strong quantitative and financial aptitude, including experience developing operational or financial calculations, models, or methodologies.
• Ability to work effectively with Product and Engineering teams and understand technical dependencies and build status.
• Strong analytical, systems-thinking, and problem-solving skills.
• Comfortable working directly in the details rather than primarily managing large teams or outside consultants.
• Ability to move quickly from problem → methodology → build → testing → implementation → measurable impact.

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Nice to Have:  

• Working knowledge of GitHub/git and software development workflows. Experience in a high growth SaaS, PaaS, fintech/tech financial services, accounting or vertical AI environment. Operational transformation and experience building AI enabled productivity, reporting, or decision support tools.