All Work, All Play | Arjun Mahesh

In this episode, we talk with Arjun Mahesh, Head of Design at Hebbia—an AI research company helping analysts go from questions to answers in seconds. From Frank Gehry’s office to Kickstarter, Stripe, Verse, and now Hebbia, Arjun’s path has taken him through nearly every type of design role across industries.From Architecture to AI DesignArjun studied architecture and computer science, but quickly realized his passion wasn’t tied to just one discipline. After working on complex digital modeling for Frank Gehry’s firm, he pivoted into product design—drawn by the speed, creativity, and freedom of the tech world.“I still love architecture. But I wanted to build things faster—and actually see them launch.”He joined a design bootcamp, moved to New York, and hasn’t looked back since.From Freelancing to Leading at ScaleAcross his career, Arjun has worked in agencies, big tech, and early-stage startups. Each phase offered a different kind of learning:* Agencies taught him how to move fast and pitch big ideas* Stripe taught him how to operate at scale and build stakeholder trust* Startups taught him how to bet on himself, own the outcome, and keep the team inspired“At Stripe, I learned doing good work is only half the job. Building trust and relationships is the other half.”Today, he leads Hebbia’s design team, shaping how AI can augment—not replace—human judgment in research-heavy fields like finance and law.Designing for AI, with AIArjun shares how designing with AI is messy, nonlinear, and full of ambiguity—but also full of creative possibility.“Designing for AI feels less like engineering and more like a science experiment. The outputs aren’t predictable, and that’s what makes it fun.”He’s also experimenting with AI tools like Midjourney and V0.dev to speed up exploration, challenge default patterns, and reimagine what interaction can look like in an AI-first world.More Than Just WorkOutside of Hebbia, Arjun makes music, DJs, writes a music newsletter, and trains for marathons.“I procrastinate by working on other projects. If I get stuck on one thing, I shift. But I always come back when I see the end.”His philosophy? Make time for play—and trust that creativity flows across everything you do.Arjun is currently hiring designers at Hebbia. You can explore open roles at design.hebbia.com, and connect with him on LinkedIn.This article accompanies our latest podcast episode featuring Arjun Mahesh. You can listen to it here on Substack, or find us on Spotify and Apple Podcasts.References:Eli Horne, Arjun’s past manager at Kickstarter who’s now leading design at Maven Clinic Collaborators at Stripe: Brad Haynes (principal designer), Rod Naber (product designer), Katie Dill (Head of Design) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thepragmaticdesigners.substack.com