Founders' Judgment and Executive Relationships

This bonus episode dives into how Cristina Cordova (Stripe’s 20th hire, early leader at Notion, now COO at Linear) spots exceptional talent early, and how she pressure-tests whether a team and product are truly worth betting on. It’s a crisp, tactical look at evaluating “spikiness,” finding beloved products (even with limited data), and building GTM the right way from day one.

Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s applying her experience building high-velocity GTM engines to the next generation of developer-first tools.

This is a clip from the full episode with Cristina (an inside look at the judgment frameworks behind Stripe, Notion, and now Linear) and the practical filters every GTM leader can use to pick winners early.

Discussed in This Clip

• How to recognize “exceptional” even outside your own domain
• Finding early proof a product is truly beloved (signals > vanity metrics)
• Starting with a sharp market wedge, then earning the right to expand
• Why founders who excel at something—anything—tend to excel at company-building
• What to expect from early operators: founder mode and bias to execute
• Sales hiring for technical buyers (and why quotas can help earlier than you think)
• Aligning tightly with founders as an exec: relationships drive outcomes
• How to assess GTM on day one: ride-alongs, raw customer feedback, ground truth

Highlights

00:00 — The difference between good and great—and how to spot it across functions

00:12 — Why this clip hit: Cristina’s framework for identifying exceptional people early

01:17 — Looking for skills you don’t have—and recognizing greatness outside your lane

03:38 — Evidence a product is beloved (Stripe on Hacker News, Notion on Twitter)

04:49 — Start with a wedge; win big later (why early enterprise skeptics don’t matter)

07:54 — “Spikiness” and unconventional signals of excellence (Minecraft servers to sales)

12:52 — What great early leaders do: see problems, create strategy, then execute

16:45 — Sales at product-led companies: hire technical sellers, set quotas sooner

21:31 — How Cristina assesses GTM on day one: ride-alongs, direct customer observation

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The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.