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Margaret Grayson

Executive Technology Leader specializing in Generative AI, platform architecture, and digital transformation

Austin, TXVP, Architecture14 years experienceExecutiveTravelE-commerceTechnology
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About

Engineering/technology leader with experience at Expedia and startup OneRail, known for building business-aligned technology roadmaps and scaling orgs rapidly (11 to 120 engineers in a year). Has driven large productivity and efficiency gains by operationalizing AI agents (code reviews, upgrades, security fixes) and implementing ChatOps-based deployment architecture, using data-driven experimentation to manage platform changes and conversion impacts.

Experience

VP, ArchitectureExpedia Group
Sr. Vice President, EngineeringLive View Technologies
Sr. Vice President, EngineeringOneRail
Vice President, Software Development & ArchitectureAmerican Homes 4 Rent
Director of Enterprise ArchitectureTrimble
Chief ArchitectHearst Autos
Sr. Technical ArchitectHumana

Education

Saint Joseph's Universitymaster, Computer Science (2002)
National Institute of Technology, Indiabachelor, Structural Engineering (1999)

Key Strengths

  • Built multi-layer technology roadmaps (category + master) aligned to business strategy at Expedia
  • Data-driven iteration to recover A/B test conversion from -2% to parity during platform merge
  • Scaled engineering org from 11 to 120 engineers in 1 year (OneRail)
  • Improved engineering productivity by ~30–40% in booking/post-booking via AI agents (Expedia)
  • Led ChatOps deployment architecture decision improving efficiency ~55–63%
  • Effective change management: overcame team pushback by piloting and demonstrating measurable results
  • Balances hands-on technical leadership by focusing on high-risk/high-reward initiatives while managing stakeholders

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Languages

English

Skills

Generative AIAgentic AIMulti-agent systemsAI orchestrationLarge language models (LLMs)Retrieval-augmented generation (RAG)AI guardrailsGeminiClaudeOpenAIGPTConversational UXReal-time searchLong-context planningDynamic negotiation