Director of Product Delivery Operations, AI

At Engine, we’re transforming business travel into something personalized, rewarding, and simple. For too long, managing travel and spend has been overwhelming and fragmented — we’re here to change that. We believe the future of travel should be seamless and powered by technology that delights customers at every step. That’s why we’re building a platform that brings together corporate travel, a powerful charge card, and modern spend management in one place.

To make this vision real, we’re looking for exceptional, mission-driven people to help redefine how businesses manage and experience travel.

More than 20,000 companies already rely on Engine to support over 1 million travelers and billions in annual bookings each year. Cash flow positive with rapid growth, we pair exclusive Engine-only rates, industry-leading rewards, and intelligent automation to help businesses save money while delivering world-class personalization and convenience.

Backed by Telescope Partners, Blackstone, and Permira, Engine has been recognized as one of the fastest-growing travel and fintech platforms in North America, with honors including the Deloitte Fast 500 and Built In’s Best Places to Work.

We are seeking a strategic, technically-fluent Director of AI, Product Delivery Ops to lead the operationalization of AI across our product ecosystem and internal workflows. This is a high-leverage leadership role for someone who has built product operations infrastructure from scratch and can now evolve it for an AI-native world. You will bridge the gap between high-level strategy and execution, ensuring our AI initiatives deliver measurable ROI while maintaining the highest standards of governance and velocity.

• →AI Operational Strategy: Serve as the primary resource for internal AI initiatives, serving as the "connective tissue" between Product, Engineering, Data, and GTM teams to prioritize high-impact AI opportunities. Your key responsibilities also include building and driving the internal AI PD Operations roadmap.
• →Product Operations Leadership: Build and lead a high-performing small AI PD Ops organization, managing individual contributors.
• →Performance & ROI Monitoring: Define and monitor AI adoption, performance, and ROI metrics, building dashboards and visibility for executive leadership to drive data-driven decision-making.
• →Infrastructure & Systems Building: Lead the design and implementation of AI-enabled workflow automations and internal tooling to reduce cycle times and increase throughput across Product Delivery (Engineering, Product, Design, Program Management).
• →Governance & Compliance: Ensure all AI tools and workflows align with firm governance, security, and compliance standards, integrating guardrails without sacrificing developer velocity.
  
  

• Experience: 10+ years of professional experience with at least 5+ years leading product operations teams.
• AI-Native Fluency: Genuine fluency with AI tools and models (e.g., Claude, Cursor, Gemini) and the ability to build and instrument processes involving AI agents and LLMs.
• Proven Track Record: Demonstrated experience building product operations infrastructure from scratch or significantly rebuilding it within a fast-growing, ambiguous environment.
• Technical Acumen: Strong data and analytics capability; comfortable with modern data stacks (Snowflake, dbt) and technical systems design.
• Execution Mindset: A "driver" who can move fast without cutting corners, with the judgment to know when to follow existing agile processes and when to evolve them for AI-native development.
• Strategic Communication: Excellent interpersonal skills with the ability to translate complex technical concepts into clear updates and business cases for senior executives.
  
  

• Drivers, Not Passengers: You own the ambiguity and chart a clear path forward.
• Conviction with Rationale: You propose and challenge ideas grounded in logic and data.
• Speed with Precision: You move at light speed while maintaining high quality and security.
• Innovate & Elevate: You constantly explore bold ideas to stay at the leading edge of AI.