Director of Product Delivery Operations, AI at Engine in Remote

About Engine 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. The Role 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. Key Responsibilities 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. What You’ll Bring to Engine 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. Engine DNA: How You’ll Work 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. Compensation Our compensation packages are based on several factors, including your experience, expertise, and location. In addition to a competitive base salary, total compensation may include equity and/or variable pay (OTE). Your recruiter will share your complete compensation package as you move through the process. Base Pay Range $195,000—$270,000 USD The Engine Edge: Perks & Compensation We believe in rewarding great work with great benefits: Compensation: Competitive base pay tied to role and experience, with opportunities for bonuses, commissions, and equity. Benefits: Check out our full list atengine.com/culture. Environments for Success: Different roles have different needs in terms of the environments that drive success which is why we have a hybrid-hub model. Whether you are in one of our amazing offices or fully remote, we’ll make sure you have what you need to succeed. Perks and benefits may vary based on employment type, location, and more. Ready to Build the Future of Work Travel? Join us on our mission to transform how work travel works—for businesses, for travelers, and for the industry. Apply now and let’s make travel simpler, smarter, and more enjoyable—together.