The Executive AI Shift: The CEO's Playbook for Maintenance Leaders

There is a real gap between talking about AI and actually transforming your business with it. Ryan Chan, UpKeep's founder and CEO, opens this 30-minute session with a direct challenge: the times AI hits hardest are when you see it in action at real companies, not just in the headlines.

The core of this session is seven AI workflows running in production at UpKeep today. They span customer support, recruiting, feature request triage, documentation, implementation project tracking, account-based marketing, and an AI executive assistant built for every customer-facing team member. Each one is live, named, and explained in plain terms.

What You’ll Learn:

• Why UpKeep decided to rebuild its internal operations using AI 18 months ago — and what it took to do it credibly.

• How an AI support agent trained on years of customer transcripts and help docs now receives customer satisfaction scores on par with human agents.

• How UpKeep automated recruiting triage, candidate scoring, and first-touch outreach — freeing human recruiters to focus entirely on building relationships.

• How UpKeep replaced a manual project management tool with an AI tracker that listens to onboarding calls, updates statuses, flags at-risk accounts, and drafts check-in emails — without being prompted.

• How every customer-facing team member now has a persistent AI executive assistant that handles pre-call briefs, post-call summaries, inbox triage, and CRM updates automatically.

The session closes with the strategic lesson that emerged from going all in: the biggest gains came not from automating single tasks, but from AI working across multiple systems in the background without needing to be prompted. That insight is the foundation of Supernova, the persistent AI agent UpKeep is now building for maintenance and operations teams.