June Cohort Fireside Chats (Jake Winckowski)

Jake Winckowski joined the June cohort fireside to discuss AI-augmented customer experience work at HackerOne. The conversation covered how increased AI-driven activity has changed support ticket volume, and how Jake built an internal Slack-based workflow with Claude Code to pull in tickets, suggest responses from historical context, and let support agents approve, edit, escalate, or resolve them. The group also discussed keeping humans in the loop for trust, security, payment, mediation, and technical troubleshooting while the team improves confidence scoring, data access, reporting, and agent-assisted support workflows.