Hi, I’m Jake. I make brands move.

I’m a brand and motion designer, currently at Stack Overflow. I’m candid about what works, and I build systems that let good work scale.

Chicago

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Working in good company

Selected work.

  1. 2022 – now

    Brand Manager

    Senior Brand Designer, 2024–2026
    Brand Designer, 2022–2024

    Led a rebrand and identity evolution with agency Koto, from first workshops to full rollout, now running the brand across product and marketing.

    See the rebrand
  2. 2025 – 2026

    Freelance Designer

    Animations, ads, product mocks, and spot illustrations for an AI scribe that lets clinicians focus on patients.

  3. 2020 – 2021

    Graphic Designer

    Matured a modern manufacturing brand into a scalable system across product, marketing, and web, as a team of one.

What I do.

Motion

Everything I make moves.

Freed.ai — animated ads and spot illustration

Systems

One system, everywhere the brand lives.

Tulip — brand refresh, guidelines, and internal tooling

Strategy

Strategy, from the first workshop on.

Stack Overflow — the rebrand, below ↓

A collage from the Stack Overflow rebrand: workshop photos from London and Nashville, a whiteboard of brand ideas, the RFP cover, sticky-note reactions, and early brand shapes and icons

The Stack Overflow rebrand.

Fifteen years in, with AI upending how developers work, Stack Overflow needed more than a refresh. We rebuilt it for where Stack was headed: verified knowledge that people and AI agents both build on.

Direction

What began as a what-if in a sync with my boss, Dave, snowballed into three months of internal research, a 40-page RFP, and finally a four-agency bake-off that ended with Koto. Internal workshops mapped our what, how, and why long before Koto ever saw the brief, then weeks of work in London with their team expanded that into strategy and tone-of-voice sessions face to face with the C-suite. We left that week with every leader aligned on the same direction, months before any visual work began.

Cover of the 40-page RFP Jake and Dave drafted to kick off the rebrand search
A “What, How, Why” brand strategy board from an early remote workshop, covered in sticky notes
A room sign reading “Poached” next to a booking panel showing the room reserved for Stack Overflow, at Koto’s London studio
Jake and the Koto team in a meeting room, a slide reading “Technology enthusiasts” on the screen behind them
Whiteboard covered in handwritten notes from a brand metaphor exercise, listing words like “Source,” “Oasis,” and “Vital”
Jake raising a pint outside a London pub after the workshop
A personality and tone-of-voice workshop board, with sticky-note reactions to sample marketing copy

System

With the direction phase complete, we really got to work. Logo, type, a brand shape system, tone of voice, and more all came together on a guidelines site our team built end to end. We met with Koto and Stack Overflow’s product team in Nashville for a brand-product intensive, sticky notes covering the walls, as we stress-tested the new brand against real interface problems. We left Nashville with a system ready for rollout to both product and marketing.

2/0032

Ascender
Cap Height
x-Height
Baseline
Descender
2
00
HeadlineNotch
An extreme close-up on the typeface, showing individual letterform details at large scale
The full “Stacks” shape system — fifteen named 2D and 3D brand shapes, from Data and DNA to Rotor and Helix
A mockup of a Stack Overflow LinkedIn post using the Stacks shape system
The new Stack Overflow icon library — a grid of outlined icons for access, billing, publishing, support, community, and settings
Slide from the Stack Overflow Business Template

01 / 20Stack Overflow Business Template

Koto and Stack Overflow working through product theming questions during a workshop in Nashville, sketches and sticky notes covering the table
The Koto and Stack Overflow teams grouped around a wall of sticky notes from the Nashville workshop
Stacked push-notification cards showing the rebrand carrying into a new product-alert design
A 404 error page using the rebrand’s 3D isometric shapes

Rollout

Then it had to ship. Over the next year the brand reached everything we touched: the launch of Stack Internal, booths from Ai4 to Microsoft Ignite, our podcasts, the Developer Survey, and every one of our Figma files, finally organized. Inside the company, the refreshed vision and mission gave Stack a clearer sense of itself, and put it in step with where the product is headed.

Sixteen Figma file covers built on the rebrand’s cover template, one per project — events, launches, the podcast, the developer survey, swag, and more
An orange Stack Overflow pencilA grey t-shirt reading “not a robot,” with the Stack Overflow logo on the sleeve
Stack Overflow brand-shape stickers on a laptop, beside the keyboard

With Dave Longworth (Senior Director, Design), Koto (brand agency), and Stack Overflow’s product and marketing teams.

Also Shipped.

The Key

An April Fools joke turned real, sellable product.

The Key
The Key
The Key
The Key
The Key
The Key

Stack’s Guide to AI

Hero and spot illustration library for a microsite guide to GenAI.

Stack’s Guide to AI
Stack’s Guide to AI
Stack’s Guide to AI
Stack’s Guide to AI
Stack’s Guide to AI
Stack’s Guide to AI

OverflowAI

Product and promo animations for AI feature launch.

OverflowAI

Stack Overflow Meetup (SOMU)

Internal meetup, brand and collateral, end to end.

Stack Overflow Meetup
Stack Overflow Meetup
Stack Overflow Meetup
Stack Overflow Meetup
Stack Overflow Meetup

What it’s like to work together.

Jake is a valued expert in the Stack brand. He provides valuable insight beyond design, particularly during the rebrand process — I so appreciate his points of view and candor.

David Longworth
Senior Director, Design,
Stack Overflow

David Longworth

I could put him in a room with a senior leader without hesitation and he’d hold his own with ease. If I had a full-time design position open, I would hire Jake immediately.

Molly Sullivan
Vice President, Brand,
Pegasystems

Molly Sullivan

Thanks so much for being such a great client. We had a wicked time working with you and Dave — I hope we get the chance to work together again.

Joe Ling
Creative Director,
Koto

Joe Ling

Jake’s systematic approach was critical to Tulip’s brand update. His token-based asset templates made it easy for the team to produce on-brand materials independently.

Madilynn Castillo
Chief Marketing Officer,
Tulip

Madilynn Castillo

Off the clock.

Æ, a display face, and Qoph, a serif

Charcoal & Ink drawings

Recent pottery

Senior Thesis exhibition catalogue and branding

Branding and vtuber design for a Twitch streamer

Branding and vtuber design for a Twitch streamer

Thanks for visiting.

If you’re curious about any of it,
reach out anytime.

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