Executives'
Club of
Chicago

A 113-year-old executive leadership institution with a name that functioned like a velvet rope. I redesigned the identity and worked with them to change the brand voice.

Creative Director / Contractor / Ashleigh Road

The Chief Innovation Officer of the Executives' Club of Chicago brought me a project that was a long time coming. The organization had been around since 1911. He wanted the new identity to feel like where the Club was going, not where it had been.

Opening materials

Project brief — Executives' Club of Chicago

Leveraging AI as My Executive Intern

A lot of this project lived in a chat window. Not to generate ideas, but to do the time-consuming groundwork that would otherwise eat a week before a single mark got made.

Sample Prompts

Audit the current brand across all touchpoints. Research the legacy identity — what did this organization look like before it became EXEC CLUB? Find competitors in the Chicago leadership org space. Map them by age, formality, and perceived accessibility. Pull inspiration that feels like 1980s Wall Street meets 1990s editorial design. Think New York Magazine layouts, early Wired, old Forbes covers. Confidence that doesn't need to explain itself. Tell me what the current brand is saying to two very different people: a CEO who's been a member for 20 years, and a recent grad who just got promoted for the first time.
Current brand: the EXEC CLUB mark reads efficient but institutional. The abbreviated wordmark with a yellow X signals precision over warmth — more directory than destination. Legacy review shows the organization carried significantly more editorial weight in earlier decades; the current mark abandoned that entirely. Competitive landscape: 12 Chicago-area leadership organizations mapped. Most cluster around formal abbreviation or civic imagery. White space in the market: authoritative but approachable. Nobody owns it. Inspiration pulled: 1980s Wall Street and 1990s editorial share a through-line — heavy serif authority, tight grid structure, black-and-white as the default with color used sparingly and on purpose. The confidence comes from restraint, not decoration. CEO read: the name signals a room you've already earned. Recent grad read: the name signals a room you're being evaluated for entry into. Same name. Two very different doors.

Total time saved throughout project: 30+ hours

What followed was several months of the same conversation: positioning, naming systems, color rationale, photography language, sub-brand logic, stakeholder deck architecture. The AI never lost the thread. It remembered, four months later, why we'd already rejected the idea I was about to propose again. That's most of the value, not the output, but the continuity. A collaborator that holds the whole project in memory so you don't have to relitigate closed arguments every time you sit back down.

The aesthetic judgment, the client navigation, the reading of the room: none of that transferred. Everything that could be synthesized, retained, or iterated in language — that kept up its end.


Process

No serif or sans-serif was left unexamined. I went from Helvetica modern to trend-wide condensed, looking for something that felt business-approachable — confident enough to sit next to a C-suite title, accessible enough that you didn't need one.

Logo explorations Logo explorations Logo explorations Logo explorations Logo explorations

Before / After

Same organization. Different door.

Before — EXEC CLUB CHICAGO
After — Executives' Club of Chicago
Before After

Eight colors organized by emotional register, not product application. Any combination holds because the system was built around what colors make people feel, not what they're supposed to label.

Harbor Blue
#4AB2BD
Guild Gold
#F0AF1E
Signal Magenta
#CC148C
Burnt Orange
#DE4B26
Evergreen
#1A3325
Lilac
#B1A8D3
Quarried White
#F9F6F0
Terminal Black
#0E1A13

Style Guide

The deliverable was a brand guide for the entire organization, alongside a toolkit that lets employees create on their own without design support. Written for non-designers — the full version for internal teams, a condensed version for external partners.

Outcomes

30+ hours saved by leveraging AI to research, consolidate reference, audit competitors, stress-test the identity, and build multiple templates and product work autonomously.

The brand was working before it was announced. Rolled out to 50+ employees before any public announcement. Adopted into LinkedIn, email, events, and sales collateral. Templates built for internal teams and external partners so the system works without supervision. The formal reveal is at a September event I've been calling Prom Night. Full buy-in at every level.

Brand Strategy Identity Design Creative Direction AI-Integrated Research Brand Systems Stakeholder Management