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Principal Software Development Engineer - Developer Productivity & Insights

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Expedia, Inc.
Full Time position
Listed on 2026-06-04
Job specializations:
  • Software Development
    AI Engineer, Data Engineer
Salary/Wage Range or Industry Benchmark: 214500 - 300000 USD Yearly USD 214500.00 300000.00 YEAR
Job Description & How to Apply Below

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 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, and career development resources to fuel our employees’ passion for travel and ensure a rewarding career journey.

Introduction to Team

Our Technology Team partners with teams across Expedia Group to create innovative products, services, and tools that deliver high‑quality experiences for travelers, partners, and employees. A singular technology platform powered by data and machine learning provides secure, differentiated, and personalized experiences that drive loyalty and traveler satisfaction.

The Principal Software Development Engineer role is part of the Developer Experience team at the intersection of Dev Ex, 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.

In

this role, you will:
  • 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 Dev Ex, 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., Linear

    B/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.
Minimum Qualifications:
  • 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…
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