I’m Dylan. Browse my work→ and my bio→
Merit America is an online career-training program for adults stuck in low-wage work. When I joined as the third hire on its product team, learners juggled coursework across email and third-party apps, and coaches tracked progress in spreadsheets. With product and engineering, I led design of the learner and coach portals that replaced them, helping the company grow from three career tracks to six, and from about 1,800 learners to more than 14,000. Behind the portals, I built our design practice, from product briefs and project trackers to user personas, managing one designer and mentoring another. For one, I wrote a “Design Stretches” guide to scoping work that became shared language across the team. The other, a UX specialist, grew into visual design by owning our navigation and design system, with my mentorship. I stayed hands-on, too: Meritbot, a Slack agent I designed, cut the number of learners falling behind nearly in half.
Bloomberg is not one business. It’s a hundred interconnected ones, with designers scattered in small groups across them. Before I stepped into this role, design leadership was more editorial-focused than product-focused, and Bloomberg Media’s IC product designers reported directly to the CPO. I gave the team a home: weekly design meetings where they could test ideas before standing behind them in their own teams; an escalation path so they didn’t absorb the company’s politics alone; and product briefs that put design needs up front. I also helped them grow: one into a design systems specialist and another into a research lead. When the pandemic and other upheavals around 2020 hit, I expanded one-on-ones to make room for moral support and harder conversations. I hired two more product designers and mentored designers on adjacent editorial, social, and marketing teams. Together, we shipped the whole subscriber journey: a homepage video module and TV hub that put free content at the top of the funnel; registration, paywall, and checkout flows, with onboarding that lifted newsletter sign-ups 42%; and AI-driven personalization to engage and retain readers. Over my time there, subscribers roughly tripled, to about 370,000.
Bloomberg Quicktake, now Bloomberg Originals, launched in 2017 as the first 24/7 video news network built for Twitter. I supported its design from 2018, and in 2020 became its creative director as it spread across social, streaming apps, network and linear TV, and Bloomberg.com. The challenges: different platforms demanded different viewer experiences, our production teams struggled to keep pace with the news, and the network itself had no coherent identity. I led its editorial design and viewer experience across every platform, directing our brand studio, an outside motion studio, and our graphics teams, and rolling out a data-driven editorial styleguide and production toolkit to dozens of editors and producers worldwide. A new brand system held it all together, recognized less by how it looks than by how it moves. A line and a circle from the original Bloomberg logo formed the Q in its wordmark, and the system adapted like a companion, shaping content to fit each viewer’s context. In its first three months, the new streaming channel averaged 7.4 million monthly viewers. Within a year of the relaunch, engagement across social and streaming was up more than 350%, and Quicktake’s core ad revenue grew 310%. The rebrand was a Shorty Awards finalist for Brand Identity.
BHIVE was Bloomberg Media’s research and prototyping lab, set up to reach audiences Bloomberg wasn’t yet serving. When I joined, the subscription business was brand new, and readers arriving from social tended to read one article and leave. I came in as a senior design lead, both to run design for the lab and to champion product innovation across the company. Our approach: meet people where they already are, give them value before asking for anything, and test fast. In 2019 alone, we ran 15 studies, five audience surveys, and four live experiments. The Bulletin used early machine learning to summarize top stories for every reader of the mobile app. Dora, an article template for social readers, tripled shares in testing. It didn’t ship whole, but its lessons, like dropping autoplay video and surfacing share links, shaped Bloomberg’s next article redesign. And Work Wise, a career calculator built with Bloomberg’s award-winning graphics team and paired with a newsletter series, drew four times Bloomberg’s average newsletter engagement, with 65% of its subscribers new to Bloomberg.
The lab was a Knight-funded team inside the Guardian US newsroom, testing experimental forms of mobile news. Since my graduate thesis at RISD, I’d argued that stories should be designed for the contexts in which people read them, so I was thrilled to join as the lab’s designer, partnering with its editorial and product directors to shape the direction of key experiments. Strange Bird asked whether a podcast host could send listeners images, data, and links in time with the audio; I conceived its chat-style player, and it became an ONA finalist. LabRdr sent commuters a personalized care package of articles timed to their commute, and tested delivering it the moment they left home or work. It also showed readers the data it tracked, so they knew how to steer its recommendations. I presented my design work at the lab’s closing conference, in a program that included speakers from The New York Times, The Washington Post, and Univision. By then, the lab’s two dozen experiments had reached hundreds of thousands of readers, and it had made its mark: it won an Online Journalism Award, worked with The Wall Street Journal and Columbia’s Tow Center on news alerts, and open-sourced its code for other newsrooms.
Casper became famous for marketing one mattress, doubling sales to more than $200 million in 2016. As it expanded into pillows, sheets, and more, the next stage of growth had to come not just from marketing but from the buyer experience. At the time, its two product designers reported to the brand design director and came from a brand studio tradition — creating stunning vertical layouts, typography, and motion graphics. What was missing was a product design practice. I came in to mentor them, and Casper soon hired me to manage them. I put new processes in place: designing from research and KPI-driven hypotheses, documenting our work in product briefs, and building rituals for feedback, in person and async. With the director of product management, I built Casper’s user testing lab, bringing in a visitor every week so we were always testing, at every stage. Both designers took to this new way of working quickly, and Anne Lee’s checkout cross-sell redesign is one shining example. The challenge: promote add-ons without risking the sale already in the cart. We explored different cart and upsell formats, guided by user feedback. In an A/B test with 466,000 users, pillow attachment rose 20% and mattress protector attachment 17%, a projected $500,000-plus in annual revenue, with checkout conversion unchanged. We launched it.
The Atavist was an online magazine of award-winning journalism, publishing one stunning multimedia longform story a month, and it licensed its in-house platform to other publishers. The problem: the platform was hard to use, and world-class results took too much custom development. As head of design, I set the vision, roadmap, and schedule for its redesign and led its UX, visual design, and brand, partnering closely with our CTO. I ran design sprints and shareouts to align a brilliant team, and each of us owned the areas where we were strongest. The new platform let writers assemble stories from modular components, themes, and navigation. Instead of “what you see is what you get,” it offered “what you see is a blueprint of what you get,” so writers could compose boldly before sweating the details. A new identity matched: a typewriter logotype and a paperclip bent into an “A.” Fast Company called it “a magic word processor.” Esquire, Vice, and Mental Floss published on it, and in the nine months after relaunch, users grew from about 26,000 to 65,000.
Etsy was not where I became a design leader. It was where I learned about design leadership. I got to work under and alongside some of the best in the industry; this was the team that won a 2014 Cooper-Hewitt National Design Award. At Etsy, I learned how leaders could lead through discourse, set standards through documentation, build togetherness through culture, and foster ownership through partnership. I worked on the International Growth team, Etsy’s top priority and the focus of a $40 million investment the year I joined, when its sellers spanned the globe but its site ran almost entirely in English. I balanced our cross-functional goals with our design team’s principles to design shop translation tools, language localization, seller onboarding, referral programs, and more. I spoke about the translation work, and the ethnographic research behind it, at an AIGA/NY event on Etsy’s product design.