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Episode 158 | February 17, 2025
Discover why Dropbox’s Alastair Simpson values effectiveness over efficiency in design, leadership, and remote work.
Are you focused on checking tasks off a list, or are you actually solving the right problems?
This is the challenge that Alastair Simpson, VP of Design at Dropbox, posed in this Insights Unlocked episode conversation with UserTesting's Jason Giles, VP of Product Design. As companies scale, many fall into the trap of measuring efficiency instead of impact—prioritizing speed and process adherence over meaningful outcomes.
In this episode, Alastair shares how he has navigated scaling design teams, leading in a Virtual-First environment, and leveraging AI in UX research. Below, we dive into his insights on why effectiveness matters more than efficiency, how to build a strong design culture, and what it takes to deliver real impact in remote work.
Many companies push for efficiency—faster sprints, streamlined workflows, and tight process control. But Alastair argues that efficiency alone isn’t enough.
Too often, he said, companies get stuck measuring adherence to process and outputs rather than focusing on the quality of outcomes.
He said there is a place for process, such as the checklist pilots follow before flying, but we also need to be remembering that our customers don't care we created a new thing, only that that whatever new thing we created solves their problems. “Did we create something meaningful for our customers?,” he said.
“At the end of the day, what matters is the outcome, not how many steps it took to get there.” – Alastair Simpson
This shift in mindset is critical for scaling design teams. As companies grow, leaders need to encourage creative problem-solving rather than rigid process adherence.
Alastair has led high-growth design teams at both Atlassian and Dropbox, two companies that scaled rapidly. A major challenge in these environments is maintaining design quality while growing fast.
His solution? Build a strong design culture anchored in key principles:
1️⃣ Regular critique – At Dropbox, design critiques happen twice a week to ensure continuous feedback.
2️⃣ Autonomy with accountability – Designers own their work beyond the Figma file—they’re responsible for how it ships.
3️⃣ Customer-centricity – Success isn’t about following a perfect design process; it’s about delivering impactful user experiences.
“I don’t care if a design went through the perfect number of iterations or if it followed some predefined process,” Simpson says. “What I care about is whether we delivered a great experience for the customer.”
By prioritizing effectiveness over efficiency, design teams can scale without sacrificing quality.
Scaling a design team is even more complex in a remote-first environment. Simpson co-led Dropbox’s transition to a Virtual-First model, where the company operates 90% remotely, with intentional in-person gatherings to build culture and collaboration.
“We don’t come together just because it’s Tuesday or Wednesday,” Alastair explains. “We gather for meaningful moments—things like quarterly retros, team offsites, or leadership workshops—where in-person collaboration truly adds value.”
“We saw the pandemic as an opportunity to design a better way of working.” – Alastair Simpson
By optimizing remote work around effectiveness rather than time logged, Dropbox has seen higher productivity, increased employee satisfaction, and access to a broader talent pool.
Another way Dropbox is increasing effectiveness over efficiency is by leveraging AI in UX research.
One of the biggest challenges in UX is knowledge retrieval—finding past research insights quickly without duplicating work. Dropbox uses an AI-powered agent to solve this. “Instead of hunting through old research documents, you can query our AI agent to find relevant studies instantly,” he said.
This is similar to UserTesting's Insights Hub.
While AI accelerates certain tasks, Alastair emphasizes that it doesn’t replace core design skills. “Design still requires human judgment and taste,” he says. “AI can help with speed, but it’s up to us to ensure we’re solving the right problems.”
The effectiveness-over-efficiency mindset isn’t just for design teams—it can transform an entire company, Jason said.
By aligning teams around outcomes rather than processes, organizations can drive better innovation, collaboration, and customer satisfaction.
At the heart of it all, effectiveness means focusing on what truly matters—delivering value, not just working faster. As Alastair said, “We need to be intentional about how we work. It’s not about efficiency for efficiency’s sake—it’s about making sure we’re solving the right problems, in the best way possible.”