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SaaStr AI: How To Sell, Scale, and Win

SaaStr AI. The top insights, lessons and learnings on how to scale faster in businesss software in the Age of AI.

Newsletter · By Jason M. Lemkin 🦄 · Official site

Indexed issues, last 90 days
8
Latest publication
Sep 29, 2026
Audience
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Earliest in this view
Jul 7, 2026

Latest issues

  1. Issue · Sep 29, 2026

    Everyone Should Publish the Deepest, Most Direct Competitive Evals They Can. Case Study: $100m ARR Gorgias for AI CX (opens the original)

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    <img alt="" class="sizing-normal" height="1480" src="https://substackcdn.com/image/fetch/$s_!eZL9!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2a568d1d-29f7-455d-960d-9f4b6da7cc6c_1158x1480.p

  2. Issue · Sep 27, 2026

    Stripe’s AI CRO on the Fastest-Growing AI Companies: 175% Growth, 48% of Revenue From Outside the Home Market, and Agents About to Read More Stripe Docs Than Human (opens the original)

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    Stripe processes payments for most of the fastest-growing AI companies in the world, so it sees their actual revenue data.At her SaaStr AI session, Maia Josebachvili, Chief Revenue Officer of AI at Stripe, walked through what Stripe is seeing across its AI customer base and how differently she would run a company if she started one today.Maia previously ran Stripe’s Enterprise business as GM. Before Stripe, she founded and ran Urban Escapes, an adventure travel company she sold to LivingSocial,

  3. Issue · Sep 23, 2026

    The SaaStr AI Guide to Building a Top-Tier Inbound AI Agent: 17,000 Conversations, ~600 Meetings Booked, and 60% More New Business (opens the original)

    Excerpt · Positive tone

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    <a class="image-link image2 is-viewable-img" href="https://cdp51.tracking.e360.salesforce.com/click?jwt=eyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9.eyJ0ZW5hbnRfaWQiOiJhMzYwL3Byb2Q1LzczZGFiZTNjMzU5MjQ3YTNhZDljNzA1NjljMWY1NGE3IiwiY3JlYXRpb25fdGltZSI6MTc5MDA4MjAyNiwibWVzc2FnZV9pZCI6IjEwcFVXMDAwMDBNNUZKVllBM18zNV80OV9TZW5kX0VtYWlsX01lc3NhZ2VfQWN0aW9uX003NzR8NjUwYmI2NGFiYzViMDBhMzExZTdmMzliMGUwZmY3ZmNmZTc4OWZkNWY4NDk2ZGI1ODQyZjhkMzg2YjY4OGFjOCMwdDQzcjhxaG1ibjNiaGFxNjJzZzVqbTUiLCJjb3JlX3RlbmFudF9pZCI6ImNvcmU

  4. Issue · Sep 9, 2026

    ElevenLabs Went From $0 to $600M+ ARR in 41 Months. When the AI Agent Closes the Deal, They Still Pay the Human. With Carles Reina, First VP of Revenue (opens the original)

    Excerpt · Neutral tone

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    Carles Reina was employee #4 at ElevenLabs and its first go-to-market hire. He was also its first investor. He spent the first nine months selling enterprise deals by himself, then built the entire commercial org, and has now moved full-time to Baobab Ventures, the $15M solo GP fund he raised last year.He came on SaaStrAI’s CRO Confidential with Sam Blond, now founder and CEO at Monaco and previously CRO at Brex and Zenefits. So this is two people who have built revenue orgs comparing notes rath

  5. Issue · Sep 2, 2026

    Harvey Puts a Former Practicing Lawyer in Every Deployment. About 180 of Them. Here's How That Model Works. (opens the original)

    Excerpt · Neutral tone

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    Everybody in B2B AI is rediscovering forward deployed engineers right now. Palantir ran the model for two decades, OpenAI built a team, and half the agent companies I talk to are hiring for some version of it.Harvey runs two versions of FDEs, and the interesting one isn’t the classic technical FDE pod. It’s the lawyers. Anique Drumright, Harvey’s Chief Product Officer, walked through both at SaaStr AI. Harvey’s forward deployed pods are mixed teams: a product manager, one or two actual lawyers,

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