Obvious · AI product design

Pinpoint:
Screenshot Annotation

A visual annotation workflow that makes precise product intent easier to communicate.

Shipped to general availability

Overview

During a three-week work trial at Obvious, I designed and shipped Pinpoint, a visual annotation workflow for directing AI-generated product changes. It began as a focused proof of concept, then evolved through engineering review into a reusable product capability.

01 / The opportunity

Make visual intent as precise as the product change itself.

When I anchored a prompt to a screenshot, I found myself writing long descriptions to explain exactly which region mattered and what should change. The problem was not a lack of context. It was the effort required to describe a precise visual target using words alone.

Pinpoint lets people annotate a screenshot directly, keeping those annotations editable and attached to the prompt sent to the agent.

02 / Scope

From one entry point to a shared product capability.

Initial entry point

Global left-rail CTA

Pinpoint first lived in one Prompt composer opened from the product’s primary action.

Shared capability

Prompt composer + Pinpoint

Engineering review led to a modular implementation on the shared composer.

Product reach

Every Prompt composer

The same annotation workflow became available wherever the composer appeared.

03 / Build

Design decisions were tested in working software.

01

Identify the communication gap. Translate a repeated prompting behavior into a clear product opportunity.

02

Build the focused proof of concept. Integrate annotation directly into one screenshot-based Prompt composer.

03

Respond to engineering review. Extend the component architecture so the workflow was modular rather than tied to one surface.

04

Refine through implementation. Use the working product to tighten states, controls, and interaction details.

04 / Interaction system

A small toolset designed for clarity and reversibility.

Arrow

Point to a target

Direct attention to a specific element without relying on spatial descriptions in the prompt.

Highlight

Define a region

Drag a box around the relevant area when the request applies to a group, section, or layout zone.

Edit + clear

Stay in control

Annotations remain editable until submission, with undo, redo, and clear-all actions for quick correction.

05 / Outcome + Reflection

A small improvement became a shared part of the product.

I built Pinpoint because I was spending too much time explaining where a visual change should happen. Giving people a faster way to point at the right place made the workflow easier for me, then useful to anyone directing the same kind of work.

The first version solved that problem in one Prompt composer. Feedback during implementation pushed the component into a more modular shape so the same capability could work wherever the composer appeared.

What mattered most was turning a repeated frustration into working software that saved time for more than just me. The feature is live today, and I can demonstrate it during interviews with an active Obvious account.

That's a wrap for this project!

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Obvious