GTM OS Weekly #36: Structure, Persistence, and Pipeline Reality

Lessons from late-stage deals, unforgettable events, and AI sales automation.

TL;DR – GTM OS Weekly #36

• Personal Update — Structure, persistence, and experience. Three reminders from this past week: structured one-on-ones compound clarity, dynamic deal tactics win when odds look lost, and events stand out only when designed as unforgettable experiences.

• GTM OS Progress Update — Walking the walk. No big launches this week, but key refinements landed in the Revenue and Content Assistants. The LinkedIn Library was restructured for faster insights, and Deep Research testing proved game-changing for competitive and account analysis.

• Playbook of the Week — AI sales automations from Lusha. Six workflows automated — list building, signals, prep, icebreakers, recaps, and coaching — freeing reps to spend 80% of their time with customers. Start with one workflow, drive adoption, and compound.

• Podcast #1 — Canva’s B2B growth. Enterprise adoption starts inside PLG motion. Track usage, add trust layers (compliance/security), and let brand love drive bottom-up pull.

• Podcast #2 — C…