Sierra, every mention

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every year anyone Jason Lemkin 5Rory O'Driscoll 2Jacob Effron 1

Verbatim, from the transcripts: the passages where Sierra comes up

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Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll Jul 15, 2026 · 2 mentions

  • ▶ 14:37 Rory O'Driscoll I put Sierra there because, you know, they just raised at fifteen billion.
  • ▶ 16:58 Rory O'Driscoll And you can squint another way and say, in fact, each of these things in and of themselves is a separate product within an overall harness that someone building an app like a Sierra might use.

Our Agent Negotiated a Vendor Renewal, Became a CFO and a Better SDR .. but has too many guardrails Jun 16, 2026 · 1 mention

  • ▶ 18:57 Jason Lemkin There's, um, you know, if you talk to folks, if you talk to folks like at Finn or Intercom or Gorgias or Sierra and others, they're all saying that there's convergence that support sales and marketing are all converging because once you…

$4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming Jun 11, 2026 · 1 mention

  • ▶ 47:52 Jason Lemkin If the craziest one are some of these CX support products, and I've done a lot of investments, worked a lot, but these Sierra Decagons, and also legal Harvey, these were niche markets before agents.

The Present and Future of AI in Sales and GTM with SaaStr's CEO and Owner's CRO Jan 21, 2026 · 1 mention

  • ▶ 39:44 Jason Lemkin And, and, and, and intercom is great at showing how Finn is better than Decagon and Sierra and like, and you know, who, which, who cares?

AI + B2B in 2026: Find the Tailwinds or Get Left Behind | Jason Lemkin Jan 2, 2026 · 1 mention

  • ▶ 34:39 Jason Lemkin Uh, Sierra went from nothing to a hundred million in one year, Decagon, lots of others.

AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin Dec 17, 2025 · 1 mention

Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI with Jacob Effron Aug 13, 2025 · 1 mention

  • ▶ 23:50 Jacob Effron And if you ask someone on the street, name an AI coding company, they'll probably say cursor or support Sierra or healthcare or bridge.
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