Principal Software Development Engineer, Developer Productivity & Insights

Expedia Group • Chicago, IL

5d

About The Position

Expedia Group brands power global travel for everyone, everywhere. We design cutting-edge tech to make travel smoother and more memorable, and we create groundbreaking solutions for our partners. Our diverse, vibrant, and welcoming community is essential in driving our success. Why Join Us? To shape the future of travel, people must come first. Guided by our Values and Leadership Agreements, we foster an open culture where everyone belongs, differences are celebrated and know that when one of us wins, we all win. We provide a full benefits package, including exciting travel perks, generous time-off, parental leave, a flexible work model (with some pretty cool offices), and career development resources, all to fuel our employees' passion for travel and ensure a rewarding career journey. We’re building a more open world. Join us. Introduction to Team: Our Technology Team partners with teams across Expedia Group to create innovative products, services, and tools to deliver high-quality experiences for travelers, partners, and our employees. A singular technology platform powered by data and machine learning provides secure, differentiated, and personalized experiences that drive loyalty and traveler satisfaction. This Principal Software Development Engineer role is part of the Developer Experience team, at the intersection of DevEx, data, and business strategy. The Developer Experience team provides tools, platforms, metrics, and enablement programs that reduce friction for engineers, streamline software delivery workflows, and improve developer satisfaction and productivity across Expedia Group. In this role, you will focus on Developer Productivity & Insights—defining how we measure and understand engineering effectiveness, partnering with platform and product teams to synthesize signals across SDLC systems and translating those insights into clear narratives and recommendations for senior engineering leadership up to the CTO office. Rather than owning a single platform, you will drive change through influence: shaping our metrics strategy, evaluating how AI is changing developer workflows, and turning data into better tools, workflows, and outcomes for engineers across Expedia Group.

Requirements

• Bachelor’s degree in Computer Science, Engineering, or a related technical field, or equivalent practical experience.
• 10+ years of software development experience delivering and operating large-scale, distributed systems or platforms, including ownership of multiple services or a significant technical domain.
• Experience leading developer relations or technical evangelism efforts at scale in enterprise or platform environments
• Proven expertise in designing and implementing service architectures, including system design (LLD), API design, and data modeling, with strong proficiency in at least one modern programming language and associated ecosystems.
• Demonstrated experience driving engineering best practices (testing, observability, performance, reliability, security) and leading complex initiatives from design through production operation.
• Familiarity with AI-driven systems, tools, or workflows and applying AI/ML concepts to real world products, with the ability to safely integrate and operate AI/ML‑enabled components within existing services.

Nice To Haves

• Experience with developer productivity, platform engineering, or horizontal core services teams, including ownership of CI/CD tooling and deploying code at scale.
• Deep, hands-on understanding of the software development lifecycle (SDLC), CI/CD pipelines, and getting code safely to production in large, distributed systems.
• Strong data science and analytics background; skilled at combining multiple data sources, applying analytical techniques, and turning findings into actionable insights for engineering leadership.
• Hands-on experience measuring developer productivity using frameworks such as DORA or SPACE
• Demonstrated executive presence with a track record of translating complex technical and data concepts into clear narratives and data stories for senior engineering and CTO-level leaders.
• Practical experience with AI developer tools (e.g., Claude, GitHub Copilot, Cursor, Codex, Kiro), including evaluating adoption, usage depth, and impact on developer workflows and outcomes, with concrete examples of using AI in day-to-day work.
• Experience building analytics and reporting that answer executive questions about AI adoption, productivity impact, and quality/reliability outcomes (e.g., monitoring and interpreting change failure rate and related metrics).

Responsibilities

• Define and evolve the end-to-end strategy, metrics framework, and data model for Developer Productivity & Insights, ensuring it aligns with industry best practices
• Design and maintain robust data pipelines, schemas, and dashboards that integrate SDLC signals (Git, CI/CD, Jira, incident/change data, AI tooling) into a coherent, trusted view of engineering effectiveness.
• Lead deep analytical investigations into developer productivity, flow, and quality, turning noisy telemetry into clear narratives, causal hypotheses, and concrete recommendations for senior engineering leadership.
• Partner with DevEx, Platform, and product teams to experiment with changes to tools, workflows, and guardrails, measuring impact (before/after) and operationalizing practices that demonstrably improve outcomes.
• Define, validate, and iterate productivity “north star” and leading indicators (e.g., repo readiness, power-user profiles, AI usage depth) and prune or simplify metrics that don’t drive decisions.
• Act as the technical owner for engineering-wide insights tooling (e.g., LinearB/SEI platforms, internal analytics services), setting standards for data quality, instrumentation, and observability.
• Collaborate closely with the CTO office and senior engineering leaders to shape AI-era productivity strategy, including how AI-assistive and agentic workflows are measured, governed, and reported.
• Mentor engineers and technical leaders on using data to run better teams—from instrumenting services and repos to interpreting metrics, designing experiments, and avoiding misuse of vanity metrics.

Benefits

• full benefits package, including exciting travel perks, generous time-off, parental leave, a flexible work model (with some pretty cool offices), and career development resources
• medical/dental/vision
• paid time off
• Employee Assistance Program
• wellness & travel reimbursement
• travel discounts
• International Airlines Travel Agent (IATAN) membership

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 5,001-10,000 employees