Stanley LinkedIn

Turning scattered conversations into an AI Head of Content system that takes initiative and compounds progress

Turning scattered conversations into an AI Head of Content system that takes initiative and compounds progress

Company

Stan

Role

Product designer

Scope

  • Research
  • Product model
  • Navigation architecture
  • Shipped UI + front-end code

Background

Stanley is an AI content partner for LinkedIn creators. It learns your voice and helps you strategize, draft, and analyze posts so that even the busiest creators and entrepreneurs can publish more content in their voice, and reach more of their audience.

Problem

When I joined the team, creators said Stanley’s voice matching was far better than any other generic AI they’d tried.

But looking at their workflow, I noticed they kept turning to other tools to supplement Stanley: collecting ideas in Notes, editing initial drafts in Docs, scheduling directly on LinkedIn.

The goal was for Stanley to operate as a Head of Content, but Stanley was falling short because the chat didn't provide a durable enough surface for content work, and Stanley took no initiative.

Solution

To rebuild Stanley as a true Head of Content, I reimagined the product as a two-part system:

  1. A hub that serves as a durable home where work is made visible and can compound

  2. A guide that proactively engages Creators across channels they already use

Stanley app screens shown on two smartphones

Mapping Creator Workflows

To build a shared picture of how creators actually worked, I ran a 300-person survey and two tracks of 30-minute interviews.

Through the survey, we pinpointed creator’s biggest challenges and their desire for AI to help in overcoming them.

What 300 creators told us

Biggest challenges
% who ranked it #1 most challenging
Coming up with strong content ideas
56%
Deciding what to post and why
40%
Staying consistent over time
37%
Turning content into real outcomes
31%
Writing in a way that feels like me
30%
Where they wanted AI help
% who selected (multi-select)
Generating content ideas
54%
Editing or refining writing
50%
Analyzing what worked and why
49%
Improving post structure or hooks
47%
Planning content ahead of time
40%
n = 300 · figures rounded to the nearest percent

To understand how effectively Stanley supports those jobs, and pinpoint where opportunities existed I also conducted 10 interviews with creators: five with non-users and five with Stanley creators.

Where Stanley supported creator workflows, and where it didn't

Strategize
Ideate
Draft
Edit
Feedback
Post
Analyze
Engage

Stanley was helping creators think - building strategies, coming up with post ideas, and providing feedback on posts. But creators were left filling gaps: collecting post ideas in Notes, copying drafts into Google Docs, and scheduling posts on LinkedIn.

The Insight: System Gaps Over Feature Gaps

Strategizing, ideation, analysis, and posting all lived only in chat, making it hard for creators to discover what Stanley could do or build on their own progress.

The Stanley app’s Ask Stanley interface

The first iteration of Stanley left memory and motivation to the creator, and we lost direction, clarity, motivation, accountability, and learning.

Direction
“where are we headed?”
Clarity
“what should I do next?”
Continuity
“where's yesterday's draft? my idea from two days ago?”
Accountability
“what needs my input vs what's already handled?”
Learning
“how does last week's performance shape this week's decisions?”
Motivation
“does this effort compound?”

Stanley wasn't missing features. It was missing the system that lets work persist beyond the chat and carry momentum

Stanley wasn't missing features. It was missing the system that lets work persist beyond the chat and carry momentum

The Head of Content Model

The reframe: stop treating Stanley as a chat box you operate, and build it like a Head of Content that sets direction and owns progress in a two-part system:

  1. A hub that provides a durable surface to hold work, track progress, and compound learning over time

  2. A guide that proactively engages across channels creators already use to create momentum and bring clarity in the moment

The Guide
proactively engages
🔔
initiates
informs
The Hub
where work compounds
Ideas
uncommitted work
Plan
committed work
Insights
performance → learning

Designing the Hub

The Hub was the foundation the entire system would sit on, so we started there.

I restructured the navigation to reflect the steps in creators' existing workflows, making Stanley's existing capabilities clear.

Then I designed the connected, durable surfaces that made progress visible, including drafts (with a full-page editor), a redesigned calendar, and an analytics page, closing the gaps creators had been filling with Notes, Docs, and external scheduling tools.

The Stanley app’s Ask Stanley chat shown on a smartphone
Stanley
Strategize
Ideate
Draft
Get Feedback
Schedule
Post
Analyze
Grow
Strategize
Ideate
Draft
Get Feedback
Schedule
Post
Analyze
Grow
Strategize
Ideate
Draft
Get Feedback
Schedule
Post
Analyze
Grow
Strategize
Ideate
Draft
Get Feedback
Schedule
Post
Analyze
Grow
The Stanley app shown on a smartphone

Building the Hub

I laid the front-end foundation, creating a token system and base components so every new surface was consistent and fast to assemble, then coded and shipped the app shell, the new navigation, the calendar redesign, and the full-page draft editor in the production React codebase.

The Stanley app dashboard in dark mode
A content workspace screen in the Stanley app

The changes I designed and shipped became central to the product experience for our direct-to-consumer application and later set the foundation for the org/agency workspace restructure that followed for our Stanley for Business product. The guide is currently being built by the team, initiating content creation workflows through iMessage, Slack, and other spaces where creators spend time.

Credits

Karin Nord - design leadership 
Thezyrie Amarouche & Yong Wang
- engineering partners
Nick Hart - Stan DS foundations
Joe Lajavic - survey analysis
Cate Podell - participant recruitment and creator insights

sARAH KOWALLIK

©2025

Vancouver

4:36:30 AM

sARAH KOWALLIK

©2025

4:36:30 AM

sARAH KOWALLIK

©2025

4:36:30 AM