CORE INSIGHT:
Everyone is arguing about which AI tools to buy.
The real fight is where the humans sit.
Conrad Goldstein mapped GTM org design across AI-native companies and found no consensus. Anthropic, OpenAI and Cohere put forward-deployed engineers in three different reporting lines. Support headcount runs at a third of the norm. And the companies selling automation doubled SDR hiring while the wider market cut it 21%.
The napkin test still applies. If your CRO cannot draw the 2027 org, you have a leadership development problem, not a tooling one.
GTM Org Design at AI-Native Companies — Conrad Goldstein
Other links and useful reads:
SHORT GTM SNIPPETS:
On the org chart nobody agrees on:
There is no reference org chart for agentic GTM. Anthropic, OpenAI and Cohere put their forward-deployed engineers in three different reporting lines, and all three are growing. That tells you the operating model is still being invented, which means your portfolio CRO copying a 2022 RevOps chart is copying the wrong decade. Board question: “Show me the org you’d build if you started today.” If the answer is the current org, dig.
On pricing legibility:
Outcome pricing has an audit problem. Zendesk books a $2 resolution when a customer goes quiet for 72 hours. Quiet is not the same as happy. If a portfolio company sells outcome-priced AI, someone on the board should ask who verifies the outcome, because that definition is now the revenue recognition policy. If it buys outcome-priced AI, same question in reverse.
On leverage per head:
High AI-adopters generate roughly $640K net new ARR per GTM head. The rest sit near $370K. That is not a talent gap, it is an operating model gap, and it is why the leaders we promoted for growing headcount need a different scorecard now. Succession reviews in 2026, not 2027.
↳ “5 ‘MAGIC’ Questions Stolen from a World-Class Coach.”
→ On a personal note, I love reminding myself of these questions. If you need help finding a Stella coach to motivate yourself or the team, look no further—you can do it yourself.
👉 HOW ARE YOU FEELING ABOUT YOUR LIFE AT WORK?
👉 HOW ARE YOU FEELING ABOUT YOUR WORK-FROM-HOME SET-UP?
👉 HOW ARE WE PERFORMING AS A COMPANY?
👉 WHAT IS IT LIKE TO WORK WITH THE REST OF THE TEAM?
👉 WHAT IS IT LIKE TO WORK WITH ME?
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