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Margaret Grayson

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

ExpediaSaint Joseph's UniversityAustin, TX14 Years ExperienceExecutive LevelWorks On-Site

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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.

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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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Experience

VP, ArchitectureExpedia Group · May 2023 – Present
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 Autos · Mar 2013 – Dec 2016
Sr. Technical ArchitectHumana · Nov 2011 – Mar 2013

Education

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

Skills

Generative AIAgentic AIMulti-agent systemsLarge language models (LLMs)Retrieval-augmented generation (RAG)ClaudeOpenAIGPTCloud-native architectureDevOpsAutomationAzure DevOpsAWSAmazon BedrockAmazon SageMaker

Languages

English

Certifications

Google AI CertificationCertified Artificial Intelligence ScientistMIT - Machine Learning - From Data to Decisions

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Executive & LeadershipExecutive & Leadership in Austin MetroGenerative AIAgentic AIMulti-Agent SystemsLarge Language Models

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Paul Stege

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VyoPathUniversity of Tulsa
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Connect with Margaret

Margaret already has a relationship with Reval, so a warm intro from us gets a much better response than cold outreach.

Typically responds within 24 hours

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Hire with Reval

Find your next great hire

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$250one-time kickoff
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Margaret GraysonExecutive Technology Leader specializing in Generative AI, platform architecture, and digital transformation