A couple of weeks ago, my three-year anniversary at Block (Cash App & Square) came and went without anybody noticing, and I actually missed it. But now that I’m looking back, I’ve been thinking about all of the growth and opportunity I’ve experienced. I feel really proud of what has come out of the whirlwind of working in a complex company during a period of significant ambiguity and challenge.
Product Level
When I started in mid-2020, it was a crazy time. COVID was still in its peak impact, businesses were suffering and companies were working on how to best adapt to meet the constantly moving challenges.
I was compelled to leave Mailchimp after my work on Stores had come to a natural stopping point and joined Square, which was significantly expanding due to market forces with the rise in entrepreneurship and e-commerce, and worked with the Risk team in their Financial Services division.
- I went from working in a hybrid model (most of my team at Mailchimp was remote in time zones across North America but I went in to the office) to a fully remote team at Square with colleagues from Ireland to Australia (to date, there are still some people I worked with who I’ve never met in person!). I love remote work, but it has its own challenges and it’s been really interesting to meet opportunities around managing up, down, and all around when communication is paramount.
- I went from working in a fairly nimble and agile environment with a robust experimentation culture and regular releases to a document-heavy culture that was much slower and more methodical to align with regulatory and compliance needs. I learned a lot about building partnerships with legal and operations partners in a way I hadn’t experienced before. Process and structure has a delicate balance between enough and too much, and it’s been really intriguing to work through how to use structure to navigate change in a way that feels manageable and healthy.
- And some other things didn’t change at all. I went from working on one huge net-new product pillar (Stores at Mailchimp) to another huge net-new product pillar (Banking at Square). The software I used stayed the same, the fidelity of my deliverables stayed the same, as did the rituals around design critiques, iterative design, planning releases, etc. The “day in the life” didn’t change dramatically which was a welcome relief.
Leadership & Management
- Over the last three years, I’ve also gotten to lead two teams and manage a truly wonderful group of designers in the United States and Australia spanning expertise from early-career to senior-level.
- I’ve gotten to partner with researchers and content designers at an IC and leads level in an embedded model that was far more mature than other orgs I’ve been in and I’ve learned a lot about the rigor and structure for building cohesive teams.
- I’ve interviewed close to 150 candidates and helped place folks on our team ranging from Director of Design, Head of Design, PM Group Lead, Principal / Staff / Senior Designer, Design Ops, etc. It turns out I genuinely love interviewing and building teams, and have been blown away by how much talent and dynamic skill sets there are out in the world.
- In the spirit of learning, I’ve educated and taught myself a lot—I haven’t had a consistent management ladder for the better part of this year and while I’ve had some wonderful interim managers, my career growth and mentorship has been largely left to me to self-navigate. I’ve attempted to do so by reading a lot, educating myself on management tactics, building my external network, seeking out mentorship, and strengthening my cross functional knowledge.
- I realized that as a design lead responsible for setting strategy, I needed to know more about the PMs and Eng leads I work with. I found and completed a certificate in Product Management through The University of Maryland to better understand and empathize with my peers on the leads team, and it has made a big difference in how I understand and prioritize work.
- I’ve leaned in to taking as many of our management courses as possible and earned the Integral Lead certificate within the company. I’ve taken all of the courses about ethical interviewing, leading remote teams, coaching, performance management, and managing within the law for domestic and international reports. Being responsible for folks’ careers is something I deeply honor and I want to make sure I’m doing it right.
- Midway through this year, I got to prepare promo defenses and deliver them in front of a panel of senior leadership on the behalf of three reports in their promo review which they all passed—it was a real highlight of the year to help others grow in their space ✨
As an IC Designer
- Through all of this, I’ve continued to work as a designer to deliver features and enhancements. I’ve recently built functional prototypes in Figma for concept testing to validate a future vision of our Support experience and it’s been fun to work with Figma’s recent updates to make an experience come to life.
- I worked on the Transfers team within Cash App to ship work related to price and fee changes, TOS updates, how customers link bank accounts, transfer money instantly, automatically add funds based on a schedule or when a balance goes low, how to best explain to customers how to send P2P funds, notify about upcoming card expirations, alert customers when there aren’t linked accounts, and a bunch of recommendations about clarifying actions that typically end in Support cases (and the interest in that work eventually led me to lead our Support design team.)
- And within all of that, it was hard to take my Ops and organization hat off. I built competitor audits, a component and template inventory, a screenshot inventory, and a source of truth for our product pillars. I’ve taken a LOT of screenshots 😅
- I ruthlessly organized my teams’ Figma spaces to use clearer titles and status updates, organize files to better visualize prior and current product status, archive old projects, and build more context around work to add more color around artboards. I designed more scannable thumbnail cards, and deleted a bunch of placeholder pages to make files easier to navigate for our XFN partners (I love a template, but if there’s no content in a page it doesn’t need to exist yet).
- We were previously getting a lot of ambiguous feedback in our design reviews, and I created a template and presented it to our other product design managers to better align idea formation, and capture feedback or actionable blockers / next steps to make design and experience reviews clearer. A number of leaders from other teams have adapted this to best use in their own way, and it feels nice to have made some influence to create organization where it was needed.