Head of AI

Jobtailor; New York (NY); On-site; USD 180,000 - 280,000; Full time

Job summary

Jobtailor in New York, NY seeks an experienced AI product leader to set the AI vision, own the product roadmap, and drive the integration of LLMs and context layers across a venture firm’s portfolio. You will lead cross-functional teams, recruit talent, and communicate complex technical decisions to diverse audiences.

You will build reusable AI foundations, evaluate model approaches, and develop metrics to quantify impact on investor workflows.

Qualifications

• 7-10+ years of experience building meaningful technical products or systems.
• Deep fluency with LLMs, agents, context/retrieval layers, evaluations, and the model landscape.
• Track record of turning ambiguous opportunities into adopted products with measurable value.
• Strong product judgment with technical depth.
• Ability to understand user behavior and prioritize high-leverage problems.
• Entrepreneurial approach to creating momentum with incomplete information.
• Experience navigating complex organizations with senior stakeholders.
• Interest in re-architecting workflows within a venture firm.
• Crisp written and verbal communication for technical and non-technical audiences.
• Ability to work in person 3+ days per week in NYC.
• Legally authorized to work in the US.
• Must answer whether employment visa sponsorship is required.

Responsibilities

• Set the AI vision and strategy with firm leadership across investing, portfolio impact, and operations.
• Own Primary's AI product roadmap, prioritization, impact metrics, and results.
• Lead development of shared context, data, infrastructure, evaluation methods, and technical primitives for trustworthy, reusable AI products.
• Evaluate LLMs, agents, retrieval and context layers, evaluations, and model approaches.
• Understand investor and operator workflows, prototype solutions, and ship products that improve decisions and outcomes.
• Create tools, standards, and support enabling others to build agents on shared foundations.
• Drive cross-functional AI integration, connect work across the firm, reduce duplication, and clarify ownership.
• Direct engineers, analysts, and other contributors; recruit talent and build a culture of technical excellence.
• Communicate strategy, roadmap, technical decisions, risks, and results to technical and non-technical audiences.

Skills

AI product strategy

LLMs

Cross-functional leadership

Product roadmaps

Context/retrieval layers

Model evaluation

Data infrastructure

User behavior analysis

Technical communication

Tools

Evaluation methods

Prototyping solutions

Data pipelines

Job description

• Set the AI vision and strategy with firm leadership across investing, portfolio impact, and operations


• Own Primary's AI product roadmap, prioritization, impact metrics, and results


• Lead development of shared context, data, infrastructure, evaluation methods, and technical primitives for trustworthy, reusable AI products


• Evaluate LLMs, agents, retrieval and context layers, evaluations, and model approaches


• Understand investor and operator workflows, prototype solutions, and ship products that improve decisions and outcomes


• Create tools, standards, and support enabling others to build agents on shared foundations


• Drive cross-functional AI integration, connect work across the firm, reduce duplication, and clarify ownership


• Direct engineers, analysts, and other contributors; recruit talent and build a culture of technical excellence


• Communicate strategy, roadmap, technical decisions, risks, and results to technical and non-technical audiences

Requirements

• 7-10+ years of experience building meaningful technical products or systems


• Deep, current, hands‑on fluency with LLMs, agents, context/retrieval layers, evaluations, and the model landscape


• Track record of turning ambiguous, zero‑to‑one opportunities into adopted products with measurable value


• Strong product judgment combined with technical depth


• Ability to understand user behavior, identify high‑leverage problems, and decide when to prototype, build, buy, or stop


• Entrepreneurial approach to creating momentum with incomplete information and taking responsibility for results


• Experience navigating complex organizations with senior stakeholders and building alignment without formal authority


• Interest in re‑architecting organizational workflows within a venture firm


• Crisp written and verbal communication for technical and non‑technical audiences


• Ability to work in person 3+ days per week in NYC


• Legally authorized to work in the US


• Must answer whether employment visa sponsorship is required

Core Competencies

Demonstrates expertise in AI product strategy, development, and integration, with a strong focus on LLMs, agents, and context layers. Proven ability to lead cross‑functional teams, communicate effectively with diverse stakeholders, and drive organizational change within a venture firm.

Highest-signal resume keywords

• AI Product Roadmap Ownership


• Hands‑On Experience with LLMs


• Cross‑Functional AI Integration


• Technical Communication Skills


• Stakeholder Alignment in Complex Organizations

ATS Optimization Keywords

Hard Skills

• AI Vision and Strategy


• Product Development


• Evaluation Methods


• Context/Retrieval Layers


• Model Evaluation


• Prototyping Solutions


• Impact Metrics


• Technical Primitives


• Data Infrastructure


• User Behavior Analysis

Soft Skills

• Entrepreneurial Mindset


• Crisp Communication


• Leadership


• Problem Identification


• Building Alignment

Industry Keywords

• Venture Firm


• Technical Excellence


• Organizational Workflows


• Product Judgment


• Stakeholder Management