Senior Principal Software Engineer - AI tools and Adoption

Yahoo Mail is the ultimate consumer inbox with hundreds of millions of users. It’s the best way to access your email and stay organized from a computer, phone or tablet. With its beautiful design and lightning fast speed, Yahoo Mail makes reading, organizing, and sending emails easier than ever.

Yahoo Mail is seeking a Senior Principal/Staff Software Engineer to lead our AI adoption initiative across the Engineering organization. You will be the driving force behind improving our 400+ engineers productivity by transforming development practices embedded with AI.

As the lead of AI initiatives in Engineering, you will orchestrate an engineering-wide transformation that makes AI-driven productivity a core engineering competency. This role requires someone who can navigate the rapidly evolving AI landscape, drive adoption across diverse teams, and deliver measurable business impact.

Responsibilities:

• Drive Cultural Transformation: Lead the evolution from AI-curious to AI-native engineering practices across all relevant teams

• Champion Change Management: Convert skeptics into advocates through data-driven demonstrations of value and hands-on enablement including Proof of concept

• Tool Evaluation & Selection: Continuously assess emerging AI tools (Copilot, Claude Code, Codex, etc.) and make data-driven recommendations based on Mail legacy Infrastructure

• Measure & Accelerate Adoption: Establish KPIs, track progress of adoption, and implement interventions to accelerate uptake

• Build Communities of Practice: Lead and create forums for knowledge sharing, celebrate wins, and foster peer-to-peer learning

• Architecture & Integration: Design technical frameworks for integrating AI tools into existing development workflows and CI/CD pipelines

• Virtual Engineer Implementation: Lead proof-of-concepts for coding agents in standardized tasks across various mail teams.

• Security & Compliance: Partner with Paranoids (Security) and Legal teams to ensure AI tool usage protects IP and meets compliance requirements

• Technical Standards: Establish best practices, guidelines, and guardrails for AI-assisted development

• Performance Optimization: Analyze and optimize the technical performance and cost-efficiency of AI tool deployments

• Innovation Pipeline: Maintain awareness of cutting-edge AI developments and identify opportunities for competitive advantage

• Remove Barriers: Identify and systematically eliminate technical, cultural, and process obstacles to AI adoption

• Communicate Impact: Regularly present adoption metrics, success stories, and ROI to engineering leadership and executives

Qualifications:

• Have experience with latest AI tech - Google Gemini, Anthropic Claude, Claude Code, ChatGPT, OpenAI Codex, GitHub Copilot

• 10+ years of software engineering experience with proven expertise across multiple programming languages and paradigms

• Deep hands-on experience with AI-powered development tools (GitHub Copilot, ChatGPT, Claude, etc.)

• Strong understanding of LLMs, prompt engineering, and AI model capabilities/limitations

• Experience with CI/CD, DevOps practices, and modern software development workflows

• Track record of evaluating and implementing new technologies at scale

• Proven ability to drive technical initiatives across large engineering organizations 

• Experience leading without authority and influencing senior technical leaders

• Track record of successful change management in engineering contexts

• Demonstrated ability to convert technical innovations into business value

• Experience driving tool adoption across diverse technical teams

• Strong communication skills with the ability to create compelling narratives for different audiences

• Patience and empathy when working with skeptics and late adopters

The material job duties and responsibilities of this role include those listed above as well as adhering to Yahoo policies; exercising sound judgment; working effectively, safely and inclusively with others;