SaaS Leaders: Ditch Legacy, Embrace AI Context Now! #shorts

Name: SaaS Leaders: Ditch Legacy, Embrace AI Context Now! #shorts
Uploaded: 2025-12-24T12:59:51+00:00
Duration: 2 min 25 s
Channel: Jason M. Lemkin
Description: In this short, Jason M. Lemkin urges SaaS CEOs and technical leaders to become disagreeable and make bold decisions to go AI‑native. He argues that…

24 Dec 2025 · 2 min

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2:25

In this short, Jason M. Lemkin urges SaaS CEOs and technical leaders to become disagreeable and make bold decisions to go AI‑native. He argues that traditional SaaS products are built around massive amounts of content—data ingestion via keyboards, cataloguing, storage, and display—but the future value will lie in context rather than raw content. Over the next five years most data will enter applications without human typing, requiring a shift to agentic data ingestion and context‑driven actions. Lemkin cites Shopify’s founder Tobi Lutke, who emphasizes providing the right context for LLMs to solve tasks, and Walden Yan of Cognition Labs, who calls context engineering the top job for AI‑agent builders. The message is a call to action: SaaS leaders must adopt AI‑native architectures, focus on context engineering, and be willing to make unpopular decisions to stay ahead.

Chapters

you're gonna have to be disagreeable as a CEO or as a technical leader making these calls to go AI native. All right, but your SaaS application does have a ton of value. We want you to move from content to context. Right now, your SaaS app has a ton of content. You have built an application that is very good at bringing in lots of data from lots of sources, cataloging it, storing it in the right places, making it easy to pull data out and be viewable by your customers. That's awesome. But in this world, the value shifts. We no longer care so much about the content itself. We care much more about the context. And what do I mean? Well, again, we have tuned all of our systems for kind of ingestion of data via a keyboard. And as I say those words, everyone in this audience is like, yeah, that's pretty old school. I mean, geez, ingestion of data via keyboard. We all recognize that that sounds old, and yet we are all going to do that hundreds of times today. So there is a big shift at play. We all know this is coming, that the world that we see today is not the world we're going to see in 5 years. Most data will come into applications, not via a keyboard over the next 5 years. So we're gonna have to take systems that are tuned to get data in one way and get data out another way to be totally different. Now in a context system, and you have an advantage in building a context system, your application should ingest data agentically and take action with context. One of the best SaaS leaders, I think, in the world, he had a bad weekend. I don't know if you, if you heard Shopify went down, but Tobi Luka is still an incredible leader. Uh, and he says that his number one job is the art of providing all the context for the task to be plausibly solvable by an LLM. So he gets it. He says, hey, Shopify's got all this data. We want it to use LLMs. I've gotta give it the right context. Walden Yan, the co-founder of Cognition Labs, the makers of Devin, an incredible AI tool, says context engineering, context engineering. Is effectively the number one job for engineers building AI agents. So you have all this content, it really can act as context for an AI agent. You are so well positioned for the future.