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This week, we sit down with Michelle Chiu, a Senior Product Designer at PayPal whose career trajectory defies traditional boundaries. From prestigious engineering fellowships at Kleiner Perkins to founding a crypto startup and styling at New York Fashion Week, Michelle bridges the gap between technical rigor and high-fashion aesthetics. In this issue, she shares how her engineering foundation fuels her design craft, the importance of "taste" in enterprise tools, and why the best designers are those who step outside the digital world to find inspiration.
You've navigated between prestigious tech giants like Meta, Coinbase, and PayPal, then ventured into the crypto-native startup world as Founding Designer at Daimo. What did building from zero at a seed-stage crypto startup teach you that your time at billion-dollar companies couldn't?
Building from zero at a seed-stage crypto startup taught me how to operate in environments where velocity and clear decision-making are essential. At Meta, Coinbase, and PayPal, I was designing within established systems—there’s rigor, scale, and incredible craft, but also layers of abstraction and support. At Daimo, every decision I made directly shaped both the product roadmap and the company narrative.
I learned how to design under extreme ambiguity, maintain craft under tight timelines, and balance ideal UX with real technical constraints. I was pushed to think not just as a designer, but as a design leader—owning the product’s long-term vision alongside day-to-day execution. Most importantly, it reinforced that great design is about making the right bets at the right moment. That sense of ownership, scrappiness, and proximity to impact is something I carry with me into any environment, regardless of scale.
Your portfolio spans both hardcore product design at companies like MongoDB and MongoDB and creative strategy in beauty and fashion with brands like Tory Burch and Carolina Herrera. How do you mentally switch between these two seemingly different worlds, and what unexpected lessons have you carried from fashion into tech design?
Product design and fashion both center on understanding people, context, and intent. The mental shift isn’t about changing how I think, but about changing which factors matter most in a given moment. In enterprise or developer tools, clarity, scalability, and system logic are paramount. In fashion and beauty, emotion, narrative, and cultural timing take the lead. The underlying discipline—designing with intention—remains the same.
The most unexpected lessons I’ve carried from fashion into tech are around taste, restraint, and timing. Fashion trains you to make decisive edits, respect the power of a strong point of view, and sharpens your sensitivity to detail—how micro choices in typography, motion, or tone can dramatically change how something feels. Those instincts translate directly into product design, especially when building interfaces that need to feel both trustworthy and aspirational. Ultimately, fashion taught me that great design isn’t just functional—it’s felt. Bringing storytelling into technical products is often what turns a usable experience into a memorable one.
From engineering intern at Microsoft and Apple to becoming a top design voice with 225K+ readers on Medium. Walk us through the moment you realized your path was shifting from engineering to design, and what gave you the courage to make that pivot?
The shift happened through a series of small realizations. While interning in engineering roles at Microsoft, Apple, and DoorDash, I found myself less energized by writing code in isolation and more drawn to the questions around who it was for, how it would feel to use, and why we were building it. I was naturally gravitating toward design conversations—sketching flows, questioning assumptions, and translating technical constraints into human-centered decisions.
What ultimately gave me the courage to pivot was recognizing that my strongest impact came from sitting at the intersection of systems thinking, storytelling, and craft. Design allowed me to combine my technical foundation with empathy, taste, and strategic judgment. I didn’t see it as leaving engineering behind, but rather reframing it as an advantage—understanding how things are built while shaping what should be built.
Sharing my thinking publicly through writing helped solidify that confidence and connect with a global community of creatives. Seeing my work resonate with hundreds of thousands of readers—and hearing from people who felt inspired to make their own pivots—affirmed that there’s real value in bridging technical rigor with creative clarity. That exchange has been both fulfilling and deeply motivating.
You were one of 57 Kleiner Perkins Engineering Fellows selected from 2,500+ applicants, yet you've spent most of your career in design roles. How has that rare engineering foundation shaped the way you approach product design differently from designers without that technical background?
Being selected as a Kleiner Perkins Engineering Fellow gave me a deep appreciation for how products actually get built. That engineering foundation continues to shape how I approach product design—I naturally think in systems, constraints, and tradeoffs. It also allows me to connect more deeply with engineering partners, enabling more effective collaboration and empathetic decision-making. I design with implementation in mind from day one, which reduces friction, shortens iteration cycles, and builds trust. It also helps me anticipate edge cases, performance implications, and technical debt early, rather than reacting to them later.
Ultimately, that foundation allows me to bridge vision and execution. It lets me advocate for high craft without losing sight of reality—and that balance is what enables products to move faster, age better, and deliver real impact at scale.
As someone who's now an Angel Investing Community Member with The Council and has worked across Web3, AI, and traditional tech, how are you personally using or integrating AI tools into your design process, and what do you think most designers are getting wrong about AI adoption right now?
I use AI as a force multiplier and integrate it into my design process during the early and supporting phases—synthesizing research, generating variations, and accelerating exploration. It’s especially useful for prototyping higher-fidelity concepts that help engineers better visualize the end product, including interactions and motion. What it doesn’t do—and shouldn’t—is make the core creative or strategic decisions for me.
What I think many designers are getting wrong about AI adoption is conflating speed with quality and output with impact. AI can generate a lot very quickly, but without a strong point of view, taste, and context, the results often feel generic or disconnected from real user needs. The most effective designers aren’t those who use AI the most—they’re the ones who know when to use it and when not to.
Ultimately, AI doesn’t replace design thinking; it amplifies it. Designers who invest in sharpening their judgment, narrative skills, and systems thinking will get far more value out of AI than those who rely on it to do the thinking for them.
You've been recognized by Adobe among 10,000+ global submissions and featured on platforms like Bestfolios and Wall of Portfolios, yet you chose to spend time as a stand-in model for NYFW shows and styling assistant roles. What drives you to seek experiences outside your comfort zone, and how have these "non-design" moments unexpectedly elevated your design work?
I seek these experiences because it helps celebrate self-growth and evolution for myself as a creative. It also stems from my belief that the best ideas happen at the intersections of fashion, art, technology, and culture. There's something powerful about becoming a student again and I enjoy actively seeking experiences that put me in rooms where I'm learning an entirely different creative language.
Being in those environments, you see how fabric moves on a body, how lighting changes a color completely, how a creative director's vision translates through an entire team under pressure. It’s influenced me to think three-dimensionally—to see how people actually interact with creative work in physical space. The way it’s translated into how I think about interface design now is asking myself questions such as where does the eye want to move? Where does interaction feel natural versus forced? These experiences outside my comfort zone don't distract from my design work—they're what keep it evolving.
We hope you enjoyed this edition of Coffee with Calyptus. Stay curious, stay inspired, and keep building what matters. Explore more editions and insightful articles at https://www.calyptus.co/blog.
