Design at AI Startups with Tovin Thomas, Founding Designer at Juicebox

​What is it actually like to be a founding designer at an AI startup like Juicebox?

​We’re sitting down with Tovin Thomas, founding designer of Juicebox to unpack the realities of building design from zero inside Series B startup.

​From defining product direction to shaping hiring decisions. We’ll get into what the job actually looks like day-to-day, how it evolves as the company grows, and what changes when you bring on your next designer.

​We’ll cover:

• ​What “founding designer” really means in practice and how the role shifts over time

• ​How to think about hiring your second designer: what to look for, what to avoid

• ​How AI is changing design workflows, tooling, and expectations

• ​What it takes to stay relevant as a designer right now

• ​Practical advice for designers trying to break into startups or update their skillset

​This session is part of Riffle’s ongoing series on design at AI-first companies, built for designers who want a clear, unfiltered view into how these teams actually operate.

​Come curious. Come with questions.