Promptless

What do they actually do

Promptless is a live SaaS tool that monitors where product changes and customer conversations happen (Git repos, issue trackers, Slack/Teams, support tools), detects when documentation should be updated, drafts the update, and surfaces it for human review. It connects to GitHub/GitLab/Bitbucket, Jira/Linear, Slack/Teams, and Zendesk/Intercom, pulling code diffs, PR metadata, tickets, and threads to produce suggested doc changes that can be opened as PRs in your docs repo or published as drafts to common doc hosts like ReadMe, Webflow, Zendesk, and Intercom (some in beta) Integrations / Triggers / GitHub integration.

Teams can run it automatically on PRs/MRs or invoke it from Slack or the web app. Review happens in the web UI, in PR comments, or inside Slack; Promptless keeps an audit trail and shows what sources informed each draft, so reviewers can edit and approve before merging/publishing How to use / Triggers.

The company is in YC W25, was founded in 2024, and lists active customers ranging from startups to at least one Fortune-500 use case. A published case study reports Promptless drafting over 50% of doc updates after adoption for one customer YC profile / Homepage / Vellum story.

Who are their target customer(s)

• Small engineering-led startups: Engineers are responsible for docs but prioritize shipping, so documentation lags. This creates repeated support questions and slows onboarding because updates aren’t written or reviewed consistently.
• Product or docs teams at high-growth companies: A small team must track changes across many repos and support channels. Most time is spent gathering context and chasing PRs, leading to slow, error-prone updates and gaps at release time.
• Customer support and success teams: Agents answer the same questions because the knowledge base is outdated or hard to update. This drives escalations to engineering and longer resolution times.
• Enterprise product teams with compliance or multi-repo setups: They need audit trails, fine-grained permissions, and consistent publishing across multiple systems. Manual workflows increase review risk and make it hard to prove who changed what.
• Developer experience / integrations teams (SDKs, public APIs, partner docs): Frequent code changes affect multiple guides and release notes. Small API changes can break examples and create inconsistent docs, increasing support load and partner friction.

How would they acquire their first 10, 50, and 100 customers

• First 10: Founder-led pilots via YC/network intros: install Promptless in target teams, tune triggers to their workflows, iterate until reviewers consistently accept drafts, and capture outcome-focused case studies like Vellum Vellum story / YC profile.
• First 50: Lean product-led motion: make GitHub/Slack/Zendesk/Intercom/ReadMe installs simple, publish step-by-step onboarding and templates, and seed value with one PR/ticket. Amplify with how‑to posts, demos in relevant communities, and a basic referral incentive Integrations.
• First 100: Add a light sales/CS motion for paid pilots with mid-market and enterprise, including SSO, multi‑org GitHub, audit logs, and security reviews. Partner with doc platforms and agencies so Promptless is recommended as the automation layer Integrations / Changelog.

What is the rough total addressable market

Top-down context:

Promptless sits across knowledge-management/documentation software (~USD 13–22B today per Mordor and Grand View), with adjacent spend in document management (~USD 7.2B) and customer service software (~USD 11B). The developer/product-facing slice of KM alone suggests a multi‑billion‑dollar opportunity Grand View / Mordor / Fortune BI / TBRC.

Bottom-up calculation:

A practical bottom‑up view: if 200k–300k software product teams globally (a subset of the ~27M developers worldwide) purchased documentation‑automation at an average $10k ARR, that implies ~$2–$3B in annual spend—consistent with a multi‑billion‑dollar SAM for developer/product‑facing docs Evans Data.

Assumptions:

• Buyer count: 200k–300k teams globally that maintain customer‑facing docs (derived from the size of the developer population and typical team sizes).
• Average contract value around $10k ARR for a cross‑tool docs automation layer (will vary by segment and integrations).
• Budgets come from KM/support/dev‑tools lines; overlap with existing doc/KB platforms is expected.

Who are some of their notable competitors

• Mintlify: Modern developer‑docs platform with AI‑assisted authoring and GitHub workflows; overlaps on drafting and review but is primarily a docs host rather than an automation layer across support/engineering tools Mintlify.
• ReadMe: API docs and developer hub platform used to publish and manage developer‑facing docs; adjacent as a publishing target and potential substitute if teams centralize on its ecosystem ReadMe.
• Paligo: Enterprise CCMS for structured technical documentation with workflow, versioning, and multi‑channel publishing; overlaps for enterprises standardizing tech docs at scale Paligo.
• Zendesk Guide: Knowledge‑base product within Zendesk used by support teams to host and manage help center articles; adjacent as a publishing destination and baseline alternative Zendesk Guide.
• Intercom Help Center: Help‑center/KB tied to Intercom’s support suite; often houses product FAQs and how‑tos and is a common publishing target for customer‑facing docs Intercom.