Insights Unlocked
Effectiveness vs. efficiency in design with Dropbox's Alastair Simpson
17 Feb 2025
Episode web page: https://bit.ly/3CBgLhw ----------------------- Rate Insights Unlocked and write a review If you appreciate Insights Unlocked, please give it a rating and a review. Visit Apple Podcasts, pull up the Insights Unlocked show page and scroll to the bottom of the screen. Below the trailers, you'll find Ratings and Reviews. Click on a star rating. Scroll down past the highlighted review and click on "Write a Review." You'll make my day. ----------------------- In this episode of Insights Unlocked, host Jason Giles sits down with Alastair Simpson, VP of Design at Dropbox, to discuss his non-traditional career journey, scaling design teams, and the evolution of remote work. Alastair shares key insights on fostering a strong design culture, navigating hypergrowth environments, and leveraging AI to enhance UX research. Tune in to learn how Dropbox’s Virtual-First model is redefining collaboration, why outcomes matter more than process adherence, and how AI is reshaping design workflows. What You’ll Learn in This Episode 🎨 Alastair’s Unconventional Path to Design Leadership How he transitioned from aspiring professional footballer to UX design leader. The role of consumer psychology in his design approach. How early career experiences—like working in a call center—helped him develop core design skills such as listening, communication, and problem-solving. 🏗️ Scaling Design Teams in High-Growth Companies Lessons from leading design at Atlassian and Dropbox during rapid expansion. Why effectiveness matters more than efficiency when managing creative teams. The importance of regular critique and how Dropbox ensures continuous feedback. 🌍 Virtual-First Work & Remote Collaboration How Dropbox designed and implemented its Virtual-First model (90% remote, 10% in-person). The concept of "core collaboration hours" and why nonlinear workdays boost productivity. The impact of remote work on trust, culture, and cross-functional collaboration. 🤖 AI’s Role in UX and Research How Dropbox is using AI-powered agents to improve access to past research. AI’s role in summarizing usability studies and enhancing design iteration speed. The balance between automation and human judgment in crafting great experiences. Key Takeaways & Quotes 💡 “Design is about building strong foundations—color, typography, layout, and interaction design. AI can enhance our workflows, but it doesn’t replace good fundamentals.” – Alastair Simpson 💡 “We don’t focus on efficiency for efficiency’s sake. Instead, we prioritize outcomes and impact.” 💡 “Virtual work doesn’t mean no in-person connection—it means intentional gatherings that matter.” Resources & Links 📌 Connect with Alastair Simpson on LinkedIn 📌 Learn more about Dropbox Design: Dropbox.Design 📌 Explore UserTesting: UserTesting.com
Full Episode
Welcome back to the Insights Unlocked podcast. In this episode, we're sitting down with Alistair Simpson, Vice President of Design at Dropbox. In his conversation with User Testing's Jason Giles, they talk about effective versus efficient design, scaling design teams, leading in a remote-first world, and the role of AI in design and research.
From his unconventional journey to design to the lessons he learned at Atlassian and Dropbox, Alistair shares insights you won't want to miss. This is a longer episode, but I promise it's worth your time. Enjoy the show.
Welcome to Insights Unlocked, an original podcast from User Testing, where we bring you candid conversations and stories with the thinkers, viewers, and builders behind some of the most successful digital products and experiences in the world, from concept to execution.
Welcome to the Insights Unlocked podcast. I'm Nathan Isaacs, Senior Manager for Content Production at UserTesting. Joining us today as host is Jason Giles, UserTesting's Vice President of Design. Welcome, Jason.
Hello, everyone. It's nice to talk to you again there, Nathan.
Yeah, nice to talk to you as well. And our guest today is Alastair Simpson. Alastair is the Vice President of Design at Dropbox, where he leads a talented and diverse design team across brand, product design, writing, and research. He previously led the design team at Atlassian.
Welcome to the show, Alastair. Thanks, Nathan. And thank you, Jason, for having me. It's a genuine pleasure to be here.
Alistair, I'm super excited. I will be honest, I've listened to a lot of your other podcasts and kind of followed you. As we talked before the show, we actually know a lot of similar people. So it's great to kind of make this connection. So I'm really thrilled about this chat. To kind of get things rolling, you have had a really fascinating career and introduction into the whole design world.
So I was hoping maybe you can talk a little bit about that unique background and then what initially drew you into design.
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