Hi Basecamp, I’m Randy — a designer, builder, and lifelong maker.

Hi 👋
Basecamp,
I’m Randy — a designer, builder, and lifelong maker.

I’ve been making things since I was a teenager in the ‘90s, drawing comic books and selling them to my classmates. I was sure I was going to work in the comics industry. But while studying cartooning at art school, I discovered Photoshop (version four!), and something just clicked. I fell in love with graphic design and shifted gears. Suddenly, I was working with specialty inks, embossing techniques, and interesting folds in print — basically, finding every creative edge I could in physical media.

But not long after, the web caught my eye.

The early 2000s were wild. Flash was still everywhere, CSS was getting exciting, and I realized this was the next big medium for creativity. So I jumped in with design and learning to code — HTML, CSS, and enough JavaScript to make things move. I’ve always believed you must understand the complete system to design well. I didn’t want to hand off ideas in a vacuum — I wanted to bring them to life.

That drive to learn and make better things has stayed with me throughout my career. I’ve built websites for universities, helped grow design teams from the ground up, created design systems used by thousands of sites, and led projects that won Webby Awards. I even host a design podcast and speak at conferences. But underneath it all, I’m still just a maker who wants to take a complex mess and turn it into something beautiful, useful, and human.

37signals/Basecamp is on the short list of companies I’ve always admired.

A decade ago, I landed a job at another one of the companies I admired: Four Kitchens. I’ve had an incredible run there — I rebuilt the creative team, led major design system initiatives, and helped institutions like NYU and Yale make major digital leaps. But after a long and successful chapter, I’m ready for something new. I want to go deep into product work. I want to focus, iterate, and ship alongside people who care deeply about doing the work right.

That’s why this role at 37signals is the perfect next step.

I’d bring a strong mix of visual design chops, systems thinking, UX strategy, and front-end know-how to the team. I’m comfortable writing production-quality HTML and CSS. I obsess over writing UI copy that makes sense. I run design critiques and ship components. I also love exploring ways to make tools more accessible, inclusive, and adaptable. I’d fit right in at 37signals, where the work starts with design and runs deep into how the product functions.

Yale design system

Yale has more than a thousand websites, and now, with its first digital design system, it can keep them all on brand.

Skip to the work

So, why am I a designer?

Because I want to make the world a little easier for people. I notice friction — clunky forms, unclear flows, frustrating messages — and I want to fix them. I believe digital experiences should be as natural and reliable as the physical world. Gravity always works. Your interface should, too.

Design is one of the most powerful tools we have to improve lives at scale.

My work on the web design for the Wu Tsai Institute is a Webby Award Nominee.

I’ve used my skills to help universities clarify their missions, nonprofits raise more funds, and even tabletop gaming companies improve their digital experiences. (I’m a giant RPG nerd — I’ve contributed to sites and games that have won ENNIE awards, the Webby-equivalents of the roleplaying world.) Whether I’m helping a friend launch their Kickstarter or working with a university to tell its story online, I bring the same care and curiosity to every project.

As for why I love the web?

It’s alive.

It responds.

It changes based on your preferences, your actions, your device.

That level of interactivity is like nothing else. I love designing for that — for the little animations that make something feel delightful, the responsive moments that surprise and delight, and the thoughtful structures that allow everyone on any device to access the same tools and info. There’s something almost magical about how a few lines of code can turn into something millions use daily.

Working on the web is also inherently inclusive. Anyone with a phone and a connection can access the same world of ideas. That’s powerful. And I want to be part of the team making that experience better, faster, and more humane.

So here I am — ready to keep building, keep learning, and hopefully, join you in shaping the next generation of useful, joyful web products. I’d love to bring my maker mindset to 37signals and help move the work forward.

oest@amazingrando.com • 412-853-4431

Randy Oest is the kind of creative leader every organization needs: innovative, detail-oriented, fluent in the technical aspects of the work, a beloved and inspiring manager, and deeply committed to both his craft and his team.

As Creative Director at Four Kitchens, he somehow manages to be both wildly imaginative and relentlessly organized. He’ll come up with a brilliant idea, execute it flawlessly, and then document the entire process in Notion with a Loom walkthrough before you’ve even finished your coffee.

Working with Rando is like using a mac: it just works the way that you would have expected even if you weren't aware of the expectation.

Randy is great with clients, delivers designs that are admired, can be relied upon in stressful situations to bring calm, and is great in a sales pitch!

Randy is an amazing facilitator—captivating, engaging, and able to guide discussions in a way that keeps teams energized and aligned.

Randy is the perfect mix of vision, strategy, and creative brilliance. He’s fun to work with, keeps teams inspired, and always delivers outstanding results

When you work with Randy one thing you'll notice is that he is always on top of his game. He is an excellent communicator and has a respected voice in the industry.

Collaborating with Randy on major website design projects is always an excellent experience. His designs are effective, not just beautiful.

Randy does a great job at both allowing me the autonomy I needed to run my project, but also stepped in to offer support and helpful feedback when needed.

Randy [as a leader] makes space for people to thrive on their own. Whenever I ever felt stuck, I could count on Randy to guide me to an answer.

Beyond his leadership, Randy is a true Notion and Figma wizard, effortlessly organizing, strategizing, and bringing creative visions to life. His ability to bridge the gap between structure and creativity makes him an invaluable asset to any team.

As a Creative Director, he guided projects and client conversations with finesse - never settling for a “just okay” option, but constantly challenging the team to deliver solutions that excited both the stakeholder and end user.