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Margaret Grayson

Executive technology leader specializing in AI transformation and scalable B2C platforms

ExpediaSaint Joseph's UniversityAustin, TX21 Years ExperienceExecutive LevelWorks On-Site

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About

Senior engineering executive and former VP of Architecture at Expedia who led a small, high-leverage architecture organization supporting an 8,000-person global engineering org. Brings a rare mix of executive people leadership and hands-on AI systems work, including OpenAI plugin integration, multi-agent booking architecture, and agentic fraud workflows that materially improved execution, automation, and customer-facing outcomes.

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Key Strengths

  • VP-level architecture leadership at Expedia
  • led senior engineering leaders with 8 senior director direct reports
  • owned end-to-end architecture for high-impact, high-ROI initiatives
  • improved team deliverable performance from 75% to 95%
  • improved operational DORA metrics by 12%
  • accelerated internal unblocking/execution by 33%
  • hands-on leadership in building Expedia booking and post-booking multi-agent architecture
  • pragmatic technical decision-making under ambiguity
  • AI/LLM product leadership through Expedia plugin with OpenAI
  • measured AI quality via conversion and user experience signals
  • applied agentic AI to fraud/risk operations
  • reduced human-in-the-loop fraud review from 1% to 0.3%
  • cut fraud transaction release time from 2 days to under 1.5 hours
  • strong cross-functional partnership with product and executive leadership
  • 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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Experience

VP, ArchitectureExpedia · May 2023 – Jan 2026
Sr. Vice President, EngineeringLive View Technologies · Oct 2022 – Mar 2023
Sr. Vice President, EngineeringOneRail · Mar 2021 – Sep 2022
Vice President, Software Development & ArchitectureAmerican Homes 4 Rent · Sep 2019 – Mar 2021
Director of Enterprise ArchitectureTrimble · Dec 2016 – Aug 2019
Chief ArchitectHearst · Mar 2013 – Dec 2016
Sr. Technical ArchitectHumana · Nov 2011 – Mar 2013
Sr. Vice President, EngineeringOneRail · Mar 2021 – Sep 2022

Education

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

Languages

English

Certifications

MIT - Machine Learning - From Data to DecisionsGoogle AI CertificationCertified Artificial Intelligence Scientist

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Connect with Margaret

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Typically responds within 24 hours

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Hire with Reval

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Margaret GraysonExecutive technology leader specializing in AI transformation and scalable B2C platforms