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<div style="display: none; max-height: 0px; overflow: hidden;">PMs are not “dying” but changing in scope depending on the organization. This article shares a framework for PMs’ past, present, and future </div>
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<h1><strong>TLDR Product Management <span id="date">2026-05-29</span></strong></h1>
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<strong>Cursor, Box, and United Airlines Talk AI-Powered Product Releases on One Virtual Stage (Sponsor)</strong>
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Product teams are shipping AI-powered features faster than ever. But how do you experiment, release, and optimize AI experiences without increasing risk?<br><br>At <a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.harness.io%2Fevent%2Fflagship%3Fcampaign_id=701Uw00000jEtPUIA0%26utm_source=tldr%26utm_medium=email-paid%23register_body/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/ABDFIuxYF0mGogKFhJZF6_dbk_jaadskIyzpg5FogSk=452" rel="noopener noreferrer nofollow" target="_blank"><span><strong>Flagship: The Feature Management and Experimentation Summit hosted by Harness</strong></span></a>, leaders from <strong><em>Cursor</em></strong>, <strong><em>Box</em></strong>, <strong><em>United Airlines</em></strong>, <strong><em>JPMC</em></strong>, <em>and more</em> will share how modern product and engineering teams are adapting feature delivery for the AI era, including how to:
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<p>Featuring sessions on feature flags, experimentation, and AI-driven product delivery.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fdpereira.substack.com%2Fp%2Fpast-present-and-future-of-pms-with%3Futm_source=tldrproduct/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/Z-QokEqj3zk4A37fNAUGnCvRRaKUA_Onq7Tr9OkIVJE=452">
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<strong>Past, present, and future of PMs (18 minute read)</strong>
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PMs are not “dying” but changing in scope depending on the organization. This article shares a framework for PMs' past, present, and future across several areas, with special emphasis on how AI and AGI pressure will reshape responsibilities.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.figma.com%2Fblog%2F4-new-ways-to-go-from-idea-to-product-with-ai-tools%2F%3Futm_source=tldrproduct/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/qYaKbANwcoW6QcMUEDCFfcTJUAg91ZbzFKRSLAmYbLk=452">
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<strong>4 new ways to go from idea to product with AI tools (4 minute read)</strong>
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AI tools are changing product development workflows. New approaches move teams from early ideas to building and production, showing what changes across the product lifecycle.
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<h1><strong>Opinions & Tutorials</strong></h1>
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fhackernoon.com%2Fwhy-ai-products-lose-users-after-the-first-try-and-how-to-design-for-adoption%3Futm_source=tldrproduct/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/xQbdu8qUBv0MFRO8Gqc_hwjHPmsh3XHsbTnnj0rK8nE=452">
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<strong>Why AI Products Lose Users After the First Try - How to Design for Adoption (7 minute read)</strong>
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AI products often lose users not because the model is weak, but because adoption design decisions are missing or wrong. There are four common failure modes: activation cliffs, a trust gap, broken correction loops, and an agent autonomy ceiling.
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<strong>I think Anthropic and OpenAI have found product-market fit (9 minute read)</strong>
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Anthropic and OpenAI have achieved PMF for enterprise coding/general-purpose agent tools. The shift is driven by real enterprise demand for products like Claude Code/Cowork and Codex, despite thin “AI cost failure” anecdotes.
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<h1><strong>Resources & Tools</strong></h1>
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fgo.prose.md%2Ftldr-prod%3Futm_source=tldr-product%26utm_medium=newsletter%26utm_campaign=openprose-2026-launch%26utm_content=secondary-w2/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/ahUfkd3w5_BvHyRVXMuEcb9D5VC2m8elPcq4RUXKrns=452">
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<strong>OpenProse: Give your agents SLAs that hold over time (Sponsor)</strong>
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Tired of babysitting agents? With <a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fgo.prose.md%2Ftldr-prod%3Futm_source=tldr-product%26utm_medium=newsletter%26utm_campaign=openprose-2026-launch%26utm_content=secondary-w2/2/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/NcsaHRmsvq1xs4uufGZ6bYrkdI_aQKPuQCYvv94m_D4=452" rel="noopener noreferrer nofollow" target="_blank"><span>OpenProse</span></a>, you define your outcome ("Inbox at zero by 5pm") - the runtime executes, watches for drift, and pings you when it's done. Write your goal once in plain English, let the system keeps it true. To start, simply open terminal and type <a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fgo.prose.md%2Ftldr-install%3Futm_source=tldr-product%26utm_medium=newsletter%26utm_campaign=openprose-2026-launch%26utm_content=secondary-w2/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/AVKpL5amBo9_mP95ABspWHdk2moZ5IDAxSqoScqD44M=452" rel="noopener noreferrer nofollow" target="_blank"><span><em>npx skills add openprose/prose</em></span></a>
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwerd.io%2Fto-reach-your-big-goal-you-need-to-sell-where-youre-heading-next%2F%3Futm_source=tldrproduct/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/giFjkkdHRIYYq24wEarlvnkZPlu_6xkRvueQReAiIKA=452">
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<strong>To reach your big goal, you need to sell where you're heading next (4 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
To achieve a big long-term goal, teams must “sell Point C”- a concrete, vivid next destination they will reach in the next 12–24 months - rather than settling for “continue existing.” This should be a strategic, fundable milestone aligned with mission, vision, strategy, and anchored in the needs of the community the team serves.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fthedesignersfieldguide.substack.com%2Fp%2Fhow-user-segmentation-rather-than%3Futm_source=tldrproduct/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/DNAZMjPFZucus8TBs_BJaS4KUVekFVUhufZ0QZSwzLI=452">
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<strong>How user segmentation, rather than personas, helps you get design buy-in (7 minute read)</strong>
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User segmentation gets more design buy-in than relying on personas alone. Personas often get dismissed, and there are four segmentation elements to reinforce personas: total audience size, time period/seasonality, device/tech context, and new vs. returning customer.
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<div style="text-align: center;"><span style="font-size: 36px;">🎁</span></div></div>
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<div style="text-align: center;"><strong><h1>Miscellaneous</h1></strong></div>
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fslack.engineering%2Fslack-ai-the-path-to-multi-cloud%2F%3Futm_source=tldrproduct/1/0100019e7332fbb6-873def86-57ec-4af5-9700-475233cf0877-000000/IZvxWPV9AP4_P1OooWNQAReS3g7sn4TsmC1mcHjLqJU=452">
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<strong>Slack AI: The Path to Multi-Cloud (17 minute read)</strong>
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