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CityScout · 2025 to 2026

CityScout, from idea to enterprise

Designing an AI-built real estate startup, from its first logo to the brand and design system that win its enterprise clients

app.cityscout.com

I've designed for CityScout since it was an idea. When it began closing multimillion-dollar deals with enterprise clients, the founders hired me as design lead, and I rebranded the company and built Athens, the design system it runs on.

Overview

The client

CityScout reads planning filings, permits, and county records and maps every development in a market. Its customers are lenders, brokers, developers, and general contractors, people who read title reports for a living and sign multimillion-dollar deals on what they find.

My role

I have worked with CityScout's founders since the company was an idea, and in August 2026 I joined as design lead. I delivered Athens, the new brand and design system, in about a month. I now design product patterns and UX, and I coach the marketing team on carrying the brand into their decks, flyers, and site.

An Athens illustration: a city block drawn as a glass model, with filings and records rising out of a single parcel

165,000+

development projects mapped by CityScout

1.3M+

residential units in those projects

30+

markets covered

A brand that reads like the public record, built for the clients who depend on it.

Juniper

#203431

Cypress

#375854

Pine

#568A84

Maple

#CD6412

Sycamore

#EBE6DD

Birch

#FAF8F5

How might we take a brand made for a scrappy launch and make it credible to enterprise clients, inside a product that AI tools keep building?

Athens prototype · tokens.css

Live prototype. A working prototype on the shipped tokens.css, with three screens in both themes and example records. Pick a pin or a project to move the selection, and use the toggle to switch between light and dark.

Open full screen ↗
The CityScout map in Athens dark
The CityScout map in Athens light
LightDark

The same map in both themes. Drag to compare them.

The CityScout home screen on a phone
A parcel view on a phone, in dark mode

From idea to enterprise

December 2025: an idea with a logo

CityScout was still an idea when I first worked with the founders. I designed its first logo, a blue and gold theme, and a small set of brand colors. They wanted a punchy, varsity spirit for the early clients they were chasing, and the brand gave them that.

2026: built fast with AI

CityScout's founders built the product mostly with Claude and other AI coding tools, and it shipped and earned money. In July I worked with them on a first pass at a system, v1 Nightingale, while the marketing site, decks, and flyers moved to a look of their own. By the summer the product used two serifs, two sans faces, stock Tailwind purples, blur shadows, and nine traffic-light statuses the map no longer used. In the founders' own words, the interface had become "very copy and paste, AI slop."

August 2026: ready for enterprise

By then CityScout was closing multimillion-dollar deals, and the punchy launch brand no longer fit the clients it was signing. The founders hired me as design lead to rebrand for that audience with an elevated, quieter feel, and to give the product one system to build on.

A rezoning record shown twice: in the 2025 varsity style, and redrawn in Athens
The 2025 landing page
2025 · Landing
The 2025 map, crowded with traffic-light pins
2025 · Map
The 2025 project list in monospace
2025 · Project list
A 2025 project page
2025 · Project
The 2026 marketing site
2026 · Marketing site
The 2026 app
2026 · App
A 2026 drawing-set page
2026 · Drawing set

Scroll sideways through the product before Athens.

Naming the failure mode

“It looks AI generated” describes a real problem and gives a designer nothing to work with, so I started by naming the specific conditions behind it. Components had drifted into several versions of the same button, because each was generated for the screen that needed it. Values were hardcoded where they were used, so a change never spread. The product still wore the personality of the library it was scaffolded from, gradients and heavy shadows stood in for hierarchy, and color appeared wherever a section wanted interest, so it carried no meaning.

AI generates each screen on its own terms, with no memory of the decisions it made elsewhere. Commitment is the part that takes a person.

What the first pass taught me

Athens: nine decisions

I came up with Athens, a brand and system built to read like the public record that CityScout sells. I wrote every choice down as one of nine decisions, so that a person or an agent applies it the same way every time.

  1. Two families, nothing else

    Newsreader sets display and page headings, and IBM Plex Sans sets everything else. The system has no italic, no monospace, no eyebrows, and no capitals for emphasis.

  2. Three token layers, one file

    Primitive ramps feed brand aliases, which feed semantic jobs. Components touch only the semantic layer, which is also the only place light and dark exist.

  3. Stage is hue, momentum is form

    Six stage hues run in pipeline order. A filled dot, a hollow ring, or a gray ring marks a project as active, stalled, or dead, and a new filing is a solid maple pin.

  4. No shadows, in either theme

    Depth comes from a surface step and a hairline. Tailwind's shadow and ring classes fail the build.

  5. Everything left-aligned

    Text, figures, dates, and headers all align left. Tabular figures line the numbers up, so right-aligned columns had nothing left to do.

  6. Icons take the color of their text

    Icons are Lucide at a 2-pixel stroke, hand-fitted at 16 and 32 pixels. Words and borders carry status, so an icon never has to.

  7. One pill in the system

    The stage badge is the only pill. Buttons, chips, and avatars are square with a 4-pixel corner.

  8. Juniper is identity, cypress is interaction

    The brand uses one teal family. Its dark step carries the logo and dark bands, its lifted step carries buttons and links, and orange is the signal.

  9. Write like the record

    Every claim shows its record, with a source and a date. Copy names the thing, such as a filing, a parcel, or a firm of record, and titles state the finding.

The Athens foundations sheet in dark: warm paper, one teal, one orange
The Athens foundations sheet in light: warm paper, one teal, one orange
LightDark

The foundations: warm paper, one teal, one orange, Newsreader for the page and Plex for the record.

The house illustration style, an architectural notebook drawn on juniper

House style: the architectural notebook, on juniper.

The lifecycle scale on the map in light and dark, compared across palettes

The lifecycle scale, built for the map.

app.cityscout.com/pipeline
The pipeline table in Athens, every figure and date left-aligned

A system the AI can be right against

One folder that engineers and agents both read

I delivered Athens as a self-contained package in CityScout's monorepo. Every value lives in one CSS file, and the docs refer to token names instead of restating values. A Tailwind config replaces the stock scales, so an off-system class fails at build time, and a rules file tells Claude how to work inside the system. A migration document maps every legacy value to its Athens token by role.

Generated code drifts when there is nothing for it to be consistent with. Once the tokens and the rules exist, each new screen an AI tool writes arrives closer to right without anyone stepping in.

The app still runs its earlier styling while the migration is planned, so the product screens on this page are prototypes built on the shipped tokens.

app.cityscout.com/sources
The source health dashboard in Athens dark

The package

724

tokens in one file

2

themes, semantic layer

11

numbered docs

164

data viz tokens

22

reference slides

4

illustration styles

Reference deck cover: The data harness for real estate development
Reference deck slide: the problem, in four numbered points
Reference deck slide on juniper: the foundational data layer
Reference deck slide comparing how early CityScout sees a project

Screens with project data are prototypes with example records.

What’s next

Patterns and UX

Athens v1 is the foundations release. I'm now designing the product's patterns and UX with the team, the work that moves the app itself onto Athens.

Coaching the marketing team

I walk the marketing team through how the brand carries into their own materials, so that a deck or a flyer they make without me still reads as CityScout.

What I learned

  1. AI moves the bottleneck from production to judgment.

    The founders built a working product without a designer. What they could not generate was a point of view, and more prompting would not have produced one, because no single output had failed.

  2. Coherence belongs to the whole product.

    Every generated screen was reasonable on its own. Only a person holding the whole product in mind could make the screens agree with each other.

  3. Give the tools something to agree with.

    I reached the same conclusion on an enterprise design system from the other direction. The most useful thing to hand AI-assisted work is a system it can be right against.

New filing

4156 Church Street

Rezoning to RM20-A, 1.2 acres

Permitting

Filing
2026-0412-ENT
Parcel
4156-018
Firm of record
Harrow & Lane Architects
Units
96

Source: county planning filing, March 3, 2026. Example record.

Live, not a screenshot: this card is built from Athens's shipped tokens.css. Switch the theme, move the project through its stages, or show which token styles each part.

New sticker!

Field notes

Little things are hidden around the site. Find all nine to earn one of my sticker designs.

On the shelf

  • The tea on the table looks a little too full.
  • Someone should top up that mug once it runs dry.
  • The plants around here like a little attention.
  • The paper lamp on the shelf has a switch.
  • The red book on the shelf opens.
  • Turn the lights off and look near the plants.

Beside the menu

  • There is a cord hanging beside the menu.

Writing & talks

  • The projector on Writing & talks is ready to roll.

Studio

  • The laptop on the Studio page could use more stickers.