Shawn Chambers

About Shawn Chambers

I build People Technology infrastructure that scales and delivers an elegent employee experience — getting the foundation right before the AI layer can deliver on its promise.Leading People Technology, Data & AI at Block (Square / Cash App). Own the full HR tech stack — Workday, Greenhouse, Docebo — across a employee organization operating in every major market.The foundation work is where most organizations have to start — and it\'s where I\'ve spent much of my career. Cleaning up Workday architectures that grew faster than the governance model that was supposed to support them. Simplifying over-engineered configurations that nobody can maintain. Establishing the data integrity, process discipline, and integration standards that turn a collection of HR tools into a coherent system. Building a People Tech stack that holds under pressure and one that buckles when the business scales.Once that foundation is solid, the next layer becomes possible. At Block, I architected an agentic employee operating system built on Model Context Protocol (MCP) architecture. Connects Workday, Greenhouse, and other people systems through an AI integration layer that automates employee and manager workflows, reduces tier-1 HR ticket volume, and surfaces intelligent recommendations without manual intervention. Team is structured around four functional lanes: Process Design, Platforms & Data, AI Integration, and Employee Experience. A model that enables speed on both the operational layer and the innovation layer simultaneously, without one crowding out the other.My background spans the full People Tech spectrum — HRIS architecture and optimization, system simplification and rationalization, vendor evaluation and negotiation, global implementations, data strategy, and AI integration. I\'ve worked closely with CHROs, CFOs, and engineering leaders to translate business problems into technology solutions that actually hold up over time.Core systems: Workday HCM · Greenhouse ATS · Docebo LMS · MCP Architecture · Agentic AI · People Analytics · HR Automation

Experience

1. Head of People Technology, Data and Ai

   Block

   Jun 2025 — Present

Education

• MIT Sloan School of Management

  MIT Sloan + CSAIL Artificial Intelligence: Implications for Business Strategy Program, Artificial Intelligence

• Western Illinois University

  Bachelor of Arts (BA), Liberal Arts and Sciences, General Studies and Humanities

  1989 — 2000

• Board of Trustees

  Bachelor's degree, Liberal Arts and Sciences, General Studies and Humanities

  2000

• Oracle University

  PeopleSoft 9.1 HCM Certification, PeopleSoft 9.1

  2011 — 2012

Skills

• Peoplesoft
• Talent Acquisition
• Oracle Fusion Middleware
• Bpo
• Offshoring
• Vendor Management
• Program Management
• Leading Organizational Change
• Erp Implementations
• Hrit
• Strategic Roadmaps
• Workforce Planning
• Outsourcing
• Human Resources
• Strategy
• Business Analysis
• Performance Management
• Consulting
• Erp
• Crm
• Leadership
• Change Management
• Management