Jim Jordan

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Grammarly

Grammarly for the Open Web

Improving writing skills at every opportunity

Work completed at Funsize

While native apps allow for deep control over the writing environment, the Grammarly Chrome extension posed a very different—and uniquely challenging—design problem:
how do you support better writing everywhere, without owning the surface you’re writing on?

My role was to help design Grammarly’s Chrome extension as a lightweight, trustworthy layer that works across millions of websites, text fields, and writing contexts—while staying out of the writer’s way.

The Challenge of the Open Web

Unlike a native editor, a browser extension has almost no guarantees:

  • Every site behaves differently
  • Text fields range from simple inputs to rich editors
  • Performance budgets are tight
  • Visual intrusion breaks trust immediately

The core challenge wasn’t just accuracy—it was restraint.

Grammarly had to:

  • Appear when helpful
  • Disappear when not
  • Respect the host page’s design
  • Work consistently across wildly inconsistent environments

Core Design Principles

1. Ubiquity Without Ownership

The extension doesn’t “own” the page. It borrows just enough space to help, then gives it back.

No permanent panels.
No hijacked layouts.
No visual dominance.

The UI adapts to the host environment rather than competing with it.


2. Progressive Disclosure of Feedback

Writing feedback unfolds in layers:

  • Inline highlights signal potential issues
  • Contextual cards explain suggestions only when engaged
  • Expanded views summarize progress and settings

This ensures writers aren’t overwhelmed—and can choose how deep they want to go.

3. Cursor- and Selection-Aware Interactions

Just like in native experiences, the Chrome extension is designed around where attention already is:

  • Suggestions anchor to the relevant word or phrase
  • Cards appear close to the text, not in distant panels
  • Actions are reversible and low-risk

Writers never lose their place.

Handling Free vs Paid Experiences

One of the more nuanced design challenges was supporting both free and paid users without creating friction or resentment.

  • Free users receive meaningful, actionable improvements
  • Advanced suggestions are clearly labeled—not hidden
  • Unsupported suggestions explain why they’re unavailable

This transparency helps maintain trust while still communicating value.


Communicating Progress & Motivation

Beyond corrections, the extension also reinforces improvement over time.

  • Lightweight writing stats
  • Weekly progress indicators
  • Positive reinforcement without gamification overload

The goal isn’t to score writing—it’s to encourage momentum.


Onboarding & Trust

Installing a writing assistant into your browser is an act of trust.

The onboarding experience was designed to:

  • Clearly explain what Grammarly does (and doesn’t do)
  • Emphasize privacy and control
  • Let users opt into features incrementally

Trust, once broken, is almost impossible to regain—so clarity mattered more than persuasion.


Designing for Constraints

Some of the most important design decisions came from constraints:

  • Limited screen real estate
  • Performance sensitivity
  • Inconsistent DOM structures
  • Accessibility requirements across unknown sites

These constraints forced the system to be:

  • Modular
  • Resilient
  • Predictable

And ultimately, better.

What I’m Most Proud Of

  • Designing an experience that works everywhere, not just ideal cases
  • Making feedback feel helpful, not judgmental
  • Balancing visibility with restraint
  • Supporting millions of writers without interrupting their flow

Closing Thoughts

Designing the Grammarly Chrome extension reinforced a belief I hold deeply:

The best tools don’t demand attention—they earn it.

On the open web, where nothing is guaranteed and everything is fragile, helping writers means knowing when to show up—and when to quietly step aside.

Native Writing Experience with Grammarly

Designing for Flow Across macOS, iOS, and iPadOS

Work completed at Funsize

During my time working with Grammarly, I focused on designing a native, cross-platform writing experience built around Grammarly’s writing-checking system at its core. The goal was simple but ambitious: make Grammarly feel invisible—present everywhere writers need help, without interrupting flow.

This work spanned macOS, iOS, and iPadOS, and required close collaboration between design, engineering, and platform teams to ensure performance, consistency, and deep OS integration.


The Design Challenge

Most writing tools treat grammar and clarity checks as an overlay—something that sits on top of text. My role was to rethink that model and design an experience where:

  • Writing assistance feels native, not bolted on
  • Feedback appears in context, not in modal interruptions
  • The system scales from phone to tablet to desktop
  • Writers stay in flow, even while revising heavily

This meant designing not just UI, but interaction models, cursor behavior, selection mechanics, and document structure.


Core Principles

1. Writing First

The interface prioritizes text above everything else. Controls fade away when not needed, and the system avoids persistent chrome that competes with the writing surface.

2. Feedback Without Friction

Grammarly suggestions are integrated directly into the editing experience—surfacing at the cursor, within selections, or contextually nearby, rather than pulling users away into side panels.

3. Platform-Native Behavior

Each platform follows its own conventions:

  • macOS embraces keyboard-driven workflows and windowed layouts
  • iOS optimizes for touch, selection handles, and compact controls
  • iPadOS bridges both, supporting multitasking and split views

Document Structure & Navigation

Long-form writing demands strong structure. I designed a dynamic table of contents that allows writers to:

  • Navigate large documents instantly
  • Reorder sections with drag-and-drop
  • Maintain orientation without breaking focus

The TOC adapts to screen size and input method, working equally well with mouse, keyboard, and touch.


Cursor-Centric Editing

A major focus was designing around the cursor, not panels or buttons.

  • Suggestions appear where attention already is
  • Selection actions are contextual and lightweight
  • Editing tools stay anchored to text, not screen edges

This approach reduces cognitive load and makes Grammarly feel like a natural extension of writing itself.


Writing Modes & Focus

To support different writing states, I designed multiple writing modes, including a focus mode that minimizes distractions and emphasizes rhythm and flow.

  • UI elements fade intelligently
  • Typography and spacing adapt to reading vs writing
  • Writers can move seamlessly between drafting and revising

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Cross-Device Consistency

Designing for macOS, iPhone, and iPad meant thinking in systems, not screens.

  • Shared interaction patterns, adapted per platform
  • Consistent Grammarly feedback behavior everywhere
  • Layouts that respond to size classes and orientation

The result is an experience that feels cohesive, whether you're editing a paragraph on your phone or revising a chapter on a Mac.


What I’m Most Proud Of

  • Making Grammarly feel built-in, not layered on
  • Preserving writer flow while delivering powerful feedback
  • Designing systems that scale from short notes to long manuscripts
  • Bridging platform conventions without compromising consistency

Closing Thoughts

Writing tools succeed when they disappear. This project pushed me to think deeply about attention, interruption, and craft—how software can support writing without demanding it.

Designing this native Grammarly experience reinforced my belief that the best productivity tools don’t shout. They whisper—right when you need them.

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