Contextual in-app guidance layer for configurable PM tools

When someone logs into a complex PM tool for the first time and sees a sidebar with twelve nested sections, they don't need a help article — they need something that watches what they're trying to do and tells them where to go. The problem isn't a lack of documentation. It's that documentation is pull-based (you have to know what to search for) and the user doesn't yet have the vocabulary to search.

PM vendors have every incentive to keep their help content generic. They serve thousands of different configurations, and building contextual guidance that adapts to a specific workspace's setup requires knowing how that workspace is actually configured — which the vendor could technically do but hasn't prioritized because enterprise customers have dedicated admins and SMB customers don't complain loudly in ways that affect renewal.

The complaint 'it can be a little hard to know where to start' and 'steep learning curve; many features were difficult to learn or hard to find' aren't about missing documentation — they're about discoverability at the moment of need. Someone trying to set up a recurring task at 2pm on a Tuesday doesn't want to open a help center tab. They want to be told, in context, where the setting is and why it exists.

This is a business because every new hire, every newly onboarded client, every role change creates a new person who needs that contextual layer. The workspace admin becomes the recurring buyer because they're the one fielding 'how do I do X?' Slack messages from their team daily — that cost is invisible but constant, and a tool that eliminates it pays for itself in the first week.

What to build

Build a browser extension that overlays step-by-step guidance on top of specific PM tools — detecting which screen the user is on via DOM parsing, then surfacing the correct next action in plain language based on a goal the user selects at the start of their session (e.g., 'set up a new client project', 'run a workload report').

Where to start

Launch for a single PM tool with a stable, well-documented frontend (Aha! or Allegra) and recruit beta users from the tool's community forum or subreddit — people who are already asking usage questions publicly are pre-qualified.

The hard part

Browser extension DOM parsing breaks every time the PM vendor ships a frontend update, so you need a monitoring system that detects breakage and alerts you before users notice — that infrastructure is non-trivial and must be built before you can scale to multiple tools.

How it makes money

Per-seat subscription billed to the workspace admin, at $6–$10 per user per month, with the admin paying for their whole team as a single invoice.