About our guest — Zach Vidibor

Zach Vidibor is the co-founder and CEO of Octave, the first context engine built specifically for GTM teams. Think of Octave as a GitHub for your go-to-market context — a structured home for your ICP, your value props, your competitive opinions, and every piece of institutional knowledge that should shape how AI and humans represent your company in market. Before founding Octave, Zach spent a decade as an operator inside companies that defined how modern GTM is done — LinkedIn, DocuSign, and Dropbox — seeing from the inside how strategy leaks and compresses by the time it reaches the frontline. Octave is his answer to that problem: a shared repo so every agent, workflow, and person on the team represents the company consistently.

Core takeaways

Context is the moat, AI is the commodity: Every team now has Claude, GPT, and Gemini. Using AI is table stakes. The alpha has to sit one layer up — in your first-party context: your codified ICP, your competitive opinions, the customers you know you don't serve and why. The lens you put between your company and the market is the defensible thing; the model behind it is not.

Wave 1 was filling fields. Wave 2 is codifying opinions: The first year of GTM engineering was dominated by enrichment — "we can now look up 30 DevOps engineers and drop them into an email." Problem solved. The next wave is interpreting what 30 DevOps engineers mean for how you act on that account — and the best teams aren't optimizing yesterday's assembly line. They're 3D-printing new motions from scratch with context as the starting input.

If you skip ICP, you will regret it: LLMs are sycophantic optimists. Without your opinions baked in as constraints, they iterate plausibly against any problem indefinitely — "GPT splits atoms until infinity." ICP isn't a static deliverable; it's a testable hypothesis the system grades itself against. Teams that skip this foundation end up producing AI-slop at scale.

Retire the set-and-forget mindset: The market's resting heart rate has gone from 60 to 120 beats a minute. VPs who still expect high conviction before every decision will lose to the ones who shift on a dime. Ten new competitors arrive per quarter. Category-defining tools appear on one-month cycles. The mindset for 2026 isn't "decide once"; it's "decide fast, shift faster, keep your context repo clean enough that changing direction is cheap."

Top quotes

> "Using AI, that's not a differentiator, right? You have to put alpha on top."

> "What about, instead of an assembly line, we 3D print this thing?"

> "The resting heart rate of the market has gone from 60 to 120 beats a minute."

> "Don't just expect the models to know what you know."

Referenced tools and resources

Context & Messaging: Octave (GitHub for your GTM context)

Data & Prospecting: Clay, Salesforce, HubSpot

AI & Agents: Claude, Claude Code, Claude Co-work, OpenAI (GPT), Google Gemini

Past operator context: LinkedIn, DocuSign, Dropbox (Zach's prior career)

Timestamps

(03:10) Welcome to season 2, and why the season shifts from hype to operating system

(04:00) Meet Zach Vidibor — co-founder and CEO of Octave, the context engine for GTM teams

(06:20) Why context is the lens between your company and your markets

(08:00) How GTM engineering has evolved in the last year — Wave 1 to Wave 2

(09:50) Using AI isn't a differentiator — you have to put alpha on top

(10:20) Why LLMs are sycophantic optimists and what that means for GTM work

(13:10) Where GTM engineering is real vs. where it's oversold

(18:30) The "3D print this thing" reframe — beyond assembly-line optimization

(19:30) Claude Code hype and what it means for solo operators vs. the enterprise

(22:10) The coordination problem Claude Code creates in scaled sales orgs

(25:00) Cut vs. grow — why you need to pick the goal before deploying AI

(26:00) "Slice the world into 50 subverticals" — what different goals actually look like

(28:00) Defining context engineering, and why ownership is still TBD

(30:00) Institutional knowledge: the "we don't sell to higher ed" problem

(34:30) The infrastructure monitoring case study — developer outbound at scale

(36:00) Brownfield vs. greenfield routing and persona-specific context

(39:40) Why the goal is positive interactions, not just demos

(41:00) Matteo on the PMM perspective — teams that skip ICP

(42:30) "If you skip, you will regret"

(43:30) How Octave structures its GTM team — forward-deployed engineers reporting to sales

(47:00) Hiring bar for great GTM engineers — taste plus systems thinking

(50:40) "Go-to-market is super quantum"

(52:30) What VPs should stop doing immediately

(53:40) The resting heart rate of the market — 60 to 120 beats a minute

Where to Find Zach

Clay

Where to Connect with Jared & Matteo

Jared Waxman, GTM Engineer School Co-founder: LinkedIn

Matteo Tittarelli, GTM Engineer School Co-founder: LinkedIn, X, Website, Newsletter

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