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Margaret Grayson
Executive technology leader specializing in AI transformation and scalable B2C platforms
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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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