Launch HN: Promptless (YC W25) – Automatic updates for customer-facing docs

60 comments

·February 18, 2025

Hi HN! I’m Prithvi, and my co-founder Frances and I built Promptless (https://gopromptless.ai), an AI teammate that proactively updates docs while you ship software.

There’s a demo video at https://youtu.be/pmslSl8dOgE, and also a “Live Demo on Your Own Docs” at https://gopromptless.ai/demo where you can plug in the URL to any existing docs site and simulate a "trigger event" to see what Promptless would have suggested. We also opened up the full product with automatic triggers for a free trial for HN this week (if you sign up at https://gopromptless.ai/hn).

We built Promptless because we wished we had it, both as doc authors and doc consumers. On the authoring side, I used to run engineering at a fintech company, and since no developer enjoys updating docs, they often went out-of-date and customers complained. On the consuming side, when we write code, we regularly run into mistakes or omissions in vendors’ or dependencies’ docs that slow us down. (This pain seems to be getting more acute with AI coding assistants, since they often rely blindly on docs.)

Promptless can be automatically triggered from new PRs or support tickets, or by manually tagging @Promptless in Slack. It integrates via OAuth with tools like Jira, Linear, and Notion, so that it has context about the intent of each change or feature. It drafts new or updated docs and can push them up to wherever docs live, like Readme, Mintlify, Intercom, Zendesk, or a Github repo.

How it works: when first connected to your docs, it starts by reviewing each page and building a “product ontology” that understands concepts, entities, and resources, as well as the relationship between them. This can take several minutes to an hour depending on the number of articles. Then, when a new trigger event occurs (such as a new PR), the Promptless agent initializes a session with several tools to find relevant context and draft new or updated documentation.

We expected early users to be most excited about automatically updating docs from new PRs, but we were surprised by other use cases from customers. For example, one has a ton of Slack Connect channels with customers, and our killer feature for them is being able to trigger an update from Slack in one click from Slack. Another has a content team separate from their product team, so for them, being able to update guides when the product team publishes release notes every two weeks is really valuable. Others value Promptless because it makes their AI support agents (like Intercom’s Fin AI) perform better, since it makes the source material more accurate and complete.

We have also published updates for several open-source projects (like Ansible, Prefect, Ray, and Ollama). Some projects have >40% of recent commits being doc updates/corrections, so having a product like Promptless that automatically suggests those doc updates can make contributing a lot easier and improve the DevEx for end-users.

We’d love for you to check us out, and we welcome any suggestions, requests, questions, or criticism! Thank you for reading!

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kylegalbraith

This idea is cool and well-scoped to a specific pain point that can be solved today. This is something that I think we need more of when it comes to YC batches.

However, you all should publish pricing before launching, and forcing me to book a call with you to use it is a nonstarter for me.

I don't want to get tied to this tool and then be charged for it in some weird way; give me your v0 pricing so that I can pay for it in a transparent way. As a fellow founder, I think you also know how little time I have for calls to check out demos for tools. So, just let me sign up and give it a spin.

prithvi2206

Yeah, this is very valid. We opened up a self-service trial this week so that people can more easily give it a spin before deciding to join a paid plan, but we're still working on a lot of the customer experience things to offer a truly complete onboarding experience. Appreciate the feedback!

prithvi2206

Forgot to post: link to try Promptless out right now is https://gopromptless.ai/hn

skeeter2020

>> and since no developer enjoys updating docs

They may be rare, but this is not universally true! I have a staff developer who creates beautiful documentation, paired with hand drawn (tablet) diagrams. I never miss an opportunity to complement & thank him for his work, he really seems to enjoy it and it goes well with the role's mandate to level-up other developers. If you find a developer (especially a senior+) who likes to create and maintain documentation, treat them like gold!

prithvi2206

Love this! Those people are definite force multipliers, but the fact that they're rare can end up putting a lot of burden on their shoulders. And yes, I definitely overgeneralized—while it's a running joke that developers hate writing docs, definitely not universally true!

smashah

As a solo-maintainer of an open source project who begs the community (to no avail) to submit PRs for the docs from their perspective, this project is definitely something I would use. I will give it a test drive over the next few days. Don't want to sound like a freeloader but are you planning on offering some sort of concessions/discounts for OSS projects? Maybe we can configure it with our own keys to take some cost off of you for our projects?

prithvi2206

Hey! We absolutely love to support open-source projects. Happy to chat with you to make sure that we can work within your budget as a solo maintainer.

anonzzzies

Can it be attached to Discord? One of the most annoying things I find is the loss of precious info in there. Even when channels are not removed or entire servers disappear, the search is so bad that no one (...) bothers and just re-asks.

prithvi2206

Exactly the right use-case. Discord has been requested a couple of times, and is coming soon! Happy to reach out when it's available.

getpost

How do you know the updated docs are correct? And what about the issue where doc training itself favors content near the beginning of the doc, but the salient facts might be near the end?

prithvi2206

Promptless tries to check its generated docs against other sources to identify errors, but there are also some very cool documentation testing tools that we might integrate in the near future!

bfeynman

kinda surprising to see basically just LLM wrappers still getting funded/interest. Neat idea obviously and nice to have, but that's sort of it. Fundamentally misses mark on what you can do already without AI (running tests on your actual doc code examples etc), and fact that any of the AI IDEs could turn part of this one with single switch to just append a doc friendly update to a commit. To think that soon we have ai agents reading ai generated docs instead of code to reduce it back down to code...

motoxpro

Ironically, the common (used to be common?) trope about foundation models being picks and shovels and LLM wrappers having no values is probably backwards. ChatGPT is the most valuable AI product and it's just a wrapper around an underlying LLM that is not 10x better than the rest of the models.

bfeynman

I would not define ChatGPT as a wrapper, anything where you are doing actual training/learning and updating weights is by most persons definition, not a wrapper. Just injecting stuff into the context or using RAG is a wrapper because there are no weight updates anywhere.

buss_jan

Very real problem. We have started to worry about how to maintain the many cookbook samples and tutorials, we wrote/are planning on writing. Going over every user facing artefact after a code change is a non-starter, so you opt for versioning these things as they'll necessary become out of date. Very excited to give this a spin soon.

alach11

Even OpenAI's cookbook is out of date in many places. This is a really difficult and common problem!

prithvi2206

Yeah, even with lots of full-time resources, companies' documentation regularly fall out of date. It's particularly ubiquitous in AI just because of how fast the general space is changing.

iknownthing

I'm curious, does it get triggered when a PR is opened or when it is merged? Because if it is when it is opened, updates to the PR could still get made which I assume would cause updates to the doc changes. Also, what if 2 PRs are opened at the same time? What if a PR is opened but never merged?

prithvi2206

Great questions! It is possible to get Promptless to run only when PRs are merged, or when commits are made on `main`, but pretty much everyone wants the doc updates to be drafted when PRs are opened, because they'd like to review the doc updates in parallel (i.e. before it's actually released). If two PRs are created at the same time, Promptless will review them separately (and potentially create two docs PRs, if both have customer-facing impact).

Honestly, some of these workflow points are areas that we're probably going to adjust and add more configuration around. For example, some folks with very high commit velocity are asking for a "daily digest" docs PR from Promptless instead of individual docs PRs.

crooked-v

Why not have a flow that automatically adds/updates stuff to the PR itself?

prithvi2206

If you're asking about when there are new commits on the source code after a PR is opened, yes that's what happens! It just updates the existing docs branch.

If you're asking if Promptless should just add doc updates to the same PR as the code PR, that's definitely an option, but people tend to just want them separate both because it fits better with their workflows and it's less contingent on CI/CD processes, if that makes sense.

martypitt

Looks great - well done!

Can you clarify the slack integration? I see you've mentioned it, but I'm unclear on the workflow.

A use-case I've thought about previously is support discussions we have on our slack channel, which indicate that we need to update our docs.

Is Promptless able to raise a PR with suggested updates on docs, based on question/answers in our support channels?

prithvi2206

Happy to clarify! There are two main ways people are using the Slack integration: (1) You click the Promptless Slack message action (video below) on a thread that might warrant a doc update—Slack Connect channels are an extremely common use-case for this, and (2) You tag @Promptless in a DM or a channel with a brief instruction—people sometimes use this for simple requests, but after signing up for Promptless, you can also send Promptless a link to an old PR, and it'll use the Github API to read the content of the PR and draft an update.

Here's a video we made a month or so ago that shows how (1) works, hope that helps! https://www.tella.tv/video/cm5x8uj9f001d0al11vyxcnsc/view

davecyen

Very needed! I’ve worked on platform teams and API docs were always rushed last second to push out a release—-but in many ways they are the product.

Another pain point was creating guides/examples for integrating 3rd party tools. Could be worth exploring

prithvi2206

For sure. It can be challenging to inculcate a culture of treating docs as a product, but since great docs can drive revenue growth and bad docs can increase churn, it's a very important mindset.

In terms of creating guides/examples for third-party tools, do you have a particular use-case in mind? e.g. if you're something like Zapier with hundreds of connections?

davecyen

Re: 3rd party integrations, think glue code for enterprise platforms (I previously worked on the developer platform at Shopify).

For example, a guide to integrate Shopify's Storefront API with Sanity CMS. These are usually a marketing/product thing more than developer docs... and almost always become obsolete after the next release and forgotten about.

Would've loved to generate a bunch of these guides and then automatically keep them up-to-date with code examples, and help serve both purposes for growth and developer docs.

prithvi2206

Yes, absolutely! Someone mentioned a similar situation where they had 100+ integration-specific landing pages in webflow (mostly for SEO) that became stale within months.

Definitely would love to pick your brain more about this if interested. prithvi@gopromptless.ai

linkjuice4all

Have any of your customers provided case study information that would imply some reduction in churn or an increase in inbound leads or sales?

prithvi2206

Yeah, great question! The earliest quantitative measurements people make are around how much time is being saved, but people are also measuring deflection rates in AI support chatbots (better docs => better support), which is strongly correlated with CSAT scores. Measuring reduction in churn or increased inbound takes several months to prove out, and we just haven't been around that long :)

We'll definitely be posting some case studies in the coming weeks, though!

lyime

Pricing? Whats bespoke about it? Whats your pricing metric?

prithvi2206

We're still seeing new customers use Promptless in new ways (hence pricing can be a bit bespoke sometimes).

But for our standard use-case, the number of docs pages (crude proxy for documentation surface area) ends up being the primary metric separating pricing tiers. We're in the process of standardizing a startup tier that probably fits most docs sites that are ~100 pages or fewer and <20 employees.

ozim

I would like to have an AI agent in web app that would have source code access and enough knowledge to explain how the app should be used.

That could be tied up with product walkthroughs so applications would give you a demo on its own and would be always up to date.

prithvi2206

Totally. My cofounder and I are very excited about this idea.

Sort of a primitive version of this, but one Promptless user is using it to update in-app tutorials for various integrations they have, in addition to public docs. The tutorials in this case are just text, but there's a path from having that context to actually having an in-app agent that provides a product walkthrough tailored for the logged-in user's unique use-case.