Head of AI

The Mission

As the primary architect of the company's AI future, you will own the entire AI product roadmap, lead dedicated AI engineering and product teams, and ensure artificial intelligence is woven into the very fabric of the product, operations, and engineering culture.

You will scale and deliver a proprietary suite of AI-native tools (Chat, Search, Inbox, and Autonomous Agents) while driving agentic engineering adoption across the entire organization to achieve massive velocity gains.

The Role

Reporting directly to the Head of Engineering and serving as a senior partner to the product leadership team, you will operate as a strategic business leader who bridges the gap between deep technical AI architecture and bottom-line business outcomes.

Product Portfolio Ownership

Take direct ownership of customer-facing AI offerings, ensuring they serve as a core competitive differentiator in the enterprise market.

AI Enablement & Transformation

Partner closely with internal business units (Ops, Finance, CX, and Sales) to accelerate and embed AI adoption within their specific workflows.

Engineering Velocity Leadership

Drive the transition to agentic engineering practices across all development pods, significantly moving the needle on organizational output.

Team Scaling & Mentorship

Recruit, develop, and retain top-tier AI engineering and product talent in a hyper-competitive market.

The Must-Haves

• Director+ Leadership: Proven experience managing, scaling, and leading cross-functional engineering and product teams at scale—not just as a high-level individual contributor.
• Production AI Track Record: Proven experience shipping actual AI-native product features to real customers, successfully navigating real-world failure modes, cost management, and scaling challenges.
• Agentic Technical Depth: Ability to easily hold your own in deep architectural debates with Staff Engineers regarding LLM system design, tool/function calling, prompt engineering, and LLM observability.
• Cross-Functional Impact: A history of driving measurable AI adoption in non-technical business functions (e.g., Finance, Sales, or Operations).
• Strategic Execution: The business acumen to define and execute a multi-quarter product roadmap in lockstep with Product, Data, and Executive leadership.

The Bonus Skills

• Ecosystem Expertise: Deep familiarity with MCP (Model Context Protocol) or the Anthropic Claude ecosystem.
• Domain Knowledge: Prior experience or deep domain expertise within Supply Chain, Warehousing, Operations, or Enterprise Logistics.
• P&L Management: Prior GM-level experience with direct P&L ownership or significant corporate resource management.

Personal Traits & Cultural Fit

• Outcome over Hype: You prioritize actual user outcomes and business efficiency over technical vanity metrics or chasing AI hype cycles.
• Radical Candor & Ownership: You exhibit extreme ownership regarding system failures, treating setbacks as opportunities for rapid learning and transparent iteration.
• Bias for Action: You thrive in high-velocity environments and possess the ability to make firm, strategic decisions even when faced with incomplete data.
• Standards-Driven: You instinctively see complex technical and operational constraints as opportunities to build creative, long-term, and highly scalable solutions.