GTM Roundtable Series: Company OS + Second Brain

GTM Roundtable: Company OS + Second Brain

As GTM teams scale, the bottleneck isn't organizing knowledge for reps to find... it's structuring your go-to-market context so AI can actually act on it. The teams pulling ahead are making their GTM motion legible to agents, so pipeline work gets done instead of waiting on the people in the room.

Join a small group of Unusual Ventures portfolio founders for an invite-only virtual roundtable on building a Company OS for your GTM team and a Second Brain for yourself.

We'll compare notes on:

Why GTM teams are graduating from Claude chat to Cowork / Code, and what changes when they do

Which GTM workflows are pulling people toward a real context layer first

What's working (and what isn't) for bootstrapping the layer and keeping it current

How everyone's bringing the less-technical half of the team along

Where people are drawing the line between shared Company OS and personal Second Brain

What makes this roundtable different:

Exclusive for Unusual Ventures portfolio founders

Limited to 8–12 attendees to enable meaningful peer discussion

60-minute interactive session

No slides

No pitching

Chatham House Rule to encourage open, honest conversation

Focused on actionable tactics over thought leadership

This is a peer discussion designed for founders to share what’s working, what’s not, and the systems they’re building inside their companies.

Moderated by Jared Waxman, Operating Partner at Unusual Ventures

Thursday, August 13, 2026

10:00–11:00 AM PT

Zoom