How 9 Years at Paperless Post Shaped My Design Leadership Philosophy

I believe people do their best work when they're engaged—when they enjoy their teammates and feel like they're constantly learning and growing. This belief shaped how I built and led the design team at Paperless Post.

Personal investment drives professional growth

Engagement doesn't happen automatically. It starts with being invested in your team members as people—authentically interested in their backgrounds, interests, and values while sharing your own. This means spending time together, listening, and paying attention to who they are beyond their work.

When people see that I genuinely care about their wellbeing and growth—that I'm invested in their success as individuals, not just their output—it transforms how feedback works. They understand that criticism comes from wanting to help them improve, not judgment.

I saw this dynamic clearly when a designer on my team asked for a promotion, but there were a few areas they needed to develop first. I was nervous about having what I thought would be a tough conversation. They were probably expecting good news, but instead I was going to share the areas they needed to work on. When we actually talked, it went really well—they agreed that those were exactly the areas they felt they needed to work on. Because we had that foundation of trust, what could have been a disappointing conversation became a collaborative growth plan.

This personal investment doesn't mean abandoning professional standards. In practice, this balance looks like maintaining clear expectations and professional boundaries. Clear expectations mean defining what success looks like for projects and being on the same page about what they're looking to improve and how to get there. Professional boundaries mean keeping personal conversations separate from work conversations and avoid gossiping.

Humility in leadership drives collective growth

Effective leadership requires knowing your own strengths and weaknesses and being secure enough to admit when you don't have all the answers. I'm transparent about what I'm working on—whether it's improving my presentation skills or learning a new aspect of the business—and I regularly ask my team for feedback.

This played out when I was invited to give a design talk for a class at Columbia Business School. I was terrified - presenting makes me incredibly nervous and I tend to blank out. Part of me wanted to decline, but I also wanted to face this fear. So I asked the team to review my slides and practiced the talk on them. I was grateful they were just as excited as I was. During the talk I was still nervous and thought I could have done better, but at the end of the day, I'm glad I did it.

This transparency and vulnerability creates space that focuses on learning and exploring, where mistakes and failures are understood as part of learning and growing.

Having humility doesn't mean lacking confidence. I can acknowledge uncertainty while still making necessary decisions and committing to a direction. The key is moving forward even without perfect information, then learning and adjusting based on the results. This shows the team that growth and adaptation are part of the process.

Curiosity drives better solutions

Everyone should be curious about what actually works best. We should all care more about finding the right answer than defending our own ideas.

Instead of hearing feedback and thinking "I have to make all these changes to make everyone happy," sometimes it means to dig deeper to understand where the person is coming from. This helps you unearth the underlying problem and decide which feedback moves you toward a better solution.

An example of this happened during a particularly challenging design review. A designer presented designs for a new product to leadership and the product team. It was a big meeting and they got feedback from a lot of people - it wasn't really the time and place to defend every idea. So we took all the feedback and went back to each person individually to dig into their concerns.

What we learned was that it wasn't really about the design. The designs made everyone think more carefully about the new product itself - was it differentiating enough from the original product? Would it bring in new use cases or just take away from the other product? Once we realized that, we were able to move the conversations forward and get a more focused problem space.

Curiosity helps you get to better solutions because it drives you to uncover more—what people are really concerned about or problems that weren't immediately obvious, not just what they're saying on the surface.

Planning drives adaptive learning

A plan is a framework and a starting point that allows you to execute, get feedback, and iterate. Rather than being rigid, effective plans are designed to evolve as you learn. In order to get to your destination, you need to pick a reasonable plan where you know what success looks like, what metrics to track, and what assumptions you're testing. It reveals what's most important and gives you a sense of where you are on your journey. This foundation lets you recognize when something isn't working and make informed decisions about whether to course-correct or pivot entirely.

We experienced this firsthand when developing FLYER, a new product designed to expand Paperless Post into casual events. Our initial hypothesis was that casual events are often created together by groups of people, so we built collaborative planning features around that assumption.

But as we tested with users, we discovered something important: truly casual events—like grabbing drinks after work—didn't actually need an artifact at all. People were comfortable just texting "drinks at 6?" Rather than forcing our original vision, we used this insight to narrow our focus. We pivoted from covering all casual events to specific types that did benefit from more intentional planning: BBQs, pool parties, game nights—events that needed coordination but weren't formal enough for traditional invitations.

This "hypothesis + test" mindset rather than "commitment + deliverable" thinking enabled us to find the right product-market fit instead of building something people didn't actually needed. The plan gave us a framework to recognize when our assumptions were wrong and make informed decisions about where to focus our efforts.

Diversity drives natural learning

I believe in building teams with complementary hard and soft skills because diversity becomes a natural learning engine. When one team member excels at presentations, another is exceptionally detailed at covering edge cases, and someone else can code prototypes, the team doesn't need me to have all the answers—they learn from each other.

This applies across both hard skills—research methods, design workflows, visual craft—and soft skills like having someone who's deeply thoughtful balanced with someone who energizes the group. Even observing different working styles is invaluable learning for the whole team.

When hiring, I look for the hard skills we need and how someone might complement the team dynamic. I observe how candidates handle ambiguous questions where they need more information, which tells me about their problem-solving approach and comfort with uncertainty. I also try to understand their working style, which helps me see both how to support them and what they might teach others.

This diversity creates constant learning opportunities where people naturally want to pick up skills and perspectives from teammates, which reinforces the engagement and curiosity that drives great work.

What This Meant in Practice

Over 9 years at Paperless Post, these beliefs guided how I grew from Product Design Lead to VP of Product Design, shaping how I approached everything from structuring career paths and establishing research practices to leading design critiques and hiring decisions. Building the right team dynamics and culture enabled everyone to do their best work.

This philosophy isn't just about managing people—it's about creating environments where great design work happens naturally because people are engaged, curious, and working together toward the best solutions. This approach helped me grow our design team from 3 to 8 people while maintaining high retention and strong cross-functional relationships. The team became known for delivering both innovative solutions and reliable execution, and when our company conducted engagement surveys, my team consistently ranked as the most engaged with the highest satisfaction scores—proof that the philosophy actually worked in practice.