In 2019, Chess.com’s HR ran on endless spreadsheets.
Fast forward to today: a 700-person global workforce, 237M+ members, and a lean 15-person HR team running it all. No IT department. No chaos. Just automation.
In this session, Brendan Woodroff, VP of People at Chess.com, breaks down how the 4 phases of automation:
Phase 1 — Reactive: Siloed systems, manual tracking, and zero visibility slowed every decision.
Phase 2 — Proactive: Unified Global HR, IT, and finance data. Real-time reporting unlocked efficient planning
Phase 3 — Optimized: End-to-end automation freed HR for strategy work—and created new roles like People Systems Analyst
Phase 4 — Future: Brendan’s vision for Global HR + IT + AI, and how automation will redefine the next decade of People Ops
Join us—and checkmate manual work.