Build the foundation that helps Flexport grow

The Infrastructure & Platform Engineering team’s mission is to provide the reliable, scalable, and cost-effective technology foundation that powers global trade. We enable Flexport’s product engineering teams to ship code faster and more securely by abstracting away infrastructure complexity.

The opportunity:

We are looking for a highly experienced Principal Technical Program Manager (TPM) to join our team! In this high-leverage role, you will bridge the gap between Engineering, Infrastructure, and Finance to ensure the efficient scaling of our technology stack.

You will own two critical mandates: Engineering Cost Efficiency and Cross-Team Infrastructure Initiatives. You will drive the strategy to optimize our cloud spend without sacrificing velocity, while simultaneously leading complex, cross-team engineering programs—such as migrations, reliability improvements, and architectural overhauls, which requires tight coordination across the entire engineering organization.

You will:

• Lead the Engineering Cost Efficiency Program: Own the roadmap for cloud cost management. Partner with Finance and Engineering leadership to define budgets, forecast spend, and identify optimization opportunities across AWS and other vendors.
• Drive Cross-Team Engineering Projects: Lead the execution of large-scale infrastructure initiatives that touch multiple engineering teams (e.g., database migrations, reliability re-architecture, service mesh implementation) from design to delivery.
• Leverage AI for Eng Operational Excellence: Champion the adoption of AI-driven tooling to modernize engineering workflows, utilizing LLMs for automated code migration/refactoring and implementing ML-based anomaly detection to catch cloud cost spikes in real-time.
• Establish Operational Excellence: Define and track KPIs related to infrastructure health, unit economics, and engineering efficiency. Create the feedback loops necessary to hold teams accountable for their usage and reliability.
• Bridge Technical & Business Worlds: Translate complex technical infrastructure challenges into clear business impact (cost, risk, speed) for executive stakeholders.
• Manage Risk & Dependencies: Proactively identify blockers in complex technical programs. Navigate trade-offs between speed, cost, and quality, ensuring stakeholders are aligned on the path forward.
• Cultivate a Culture of Efficiency: Evangelize best practices for resource utilization and architectural efficiency. Empower engineering teams with the data and tools they need to make cost-aware decisions.
• Communication & Reporting: Produce clear, concise artifacts for communicating status, progress, risks, and financial savings to the engineering leaders and executive leadership.

You should have:

• 10+ years of experience in Technical Program Management, Engineering Management, or a related technical field.
• Deep understanding of Cloud Infrastructure (AWS preferred) and SaaS economics. You understand how architectural decisions impact the bottom line.
• Proven experience leading Cost Efficiency programs or managing significant cloud budgets at scale.
• Experience applying AI/ML technologies to drive operational efficiency, such as using LLMs for developer productivity, automating workflows, or enhancing data analysis.
• Experience managing large-scale, cross-functional technical programs involving distributed systems, microservices, infrastructure and security practices.
• Strong analytical skills: You are comfortable diving into large datasets (SQL, Excel/gsheets) to model costs, forecast trends, and find anomalies.
• Ability to influence without authority: You can drive consensus across autonomous engineering teams and negotiate with senior leadership.
• Excellent written and verbal communication skills, with the ability to switch context between deep technical architecture and high-level business strategy.
• Bachelor's degree in Computer Science, Engineering, or relevant technical work experience.

Bonus points if you have:

• Background in logistics, supply chain, or high-volume transactional marketplaces.

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