This article describes how the design team at Flexport developed over the last 3 years. It covers the team’s evolution, roles, meetings, processes and systems.

The team is still relatively small. Most of our learning is ahead of us. However, I think this article provides helpful insights for designers tasked with building a team in an uncertain startup environment.

*Unfortunately, there is no blueprint

Context defines how a design team forms and functions within a company. Every situation is unique. Therefore, a formula to build the perfect design team does not exist. This is especially true in a startup, where discovering new business and organizational models is key to success.

The Beginning

I joined Flexport when there were a few employees in a small office in SOMA. I was tasked with all things design, with product design as the priority.

I designed our client, partner, and internal apps, as well as our public facing website and brand material. It was a lot of work and a lot of fun collaborating with business leaders, engineers and our product manager. The design decisions we made — good and bad — formed the foundation of our product and brand identity.

The most important thing I did during this time was to get out of the office and meet our clients. The many user interviews I conducted were invaluable.

Screenshots of Flexport’s Client app

Flexport has since grown into a company of 350+ employees with offices in New York, Amsterdam, Shenzhen, Hong Kong, Los Angeles, Atlanta, and San Francisco. We’ve raised $94M from investors, including Peter Thiel’s Founders Fund, Google Ventures, First Round Capital, Bloomberg Beta, Y Combinator, & more.

Flexport’s public website

As Flexport grew, so too did our design needs.

Following advice from Flexport’s founder Ryan Petersen on how to scale a team, I made a list of everything I worked on over the last year, and categorized it under three roles:

• Product Designer (IxD, VD)
• User Researcher
• Communication Designer

This list informed the hiring plan. After talking it over with my manager, we determined our first hire should be able to bridge the gap between design and engineering. We started our search for a UI engineer/designer, and were lucky to find Andrew Kaye.

The Centralized Pair

After Kaye joined, life became better. There was finally another person at Flexport who understood the role of design and could help with the increasing workload. He had the unique ability to translate beautiful design into our complex codebase, and a cool dog named “<div>,” which he often brought to the office.

Shortly after he joined, we opened up two product design positions. We posted the positions on Dribbble, Hacker News, and our careers page. Our recruiting team began out-bounding potential candidates. Kaye and I reviewed their work and experience level. If we thought the candidate was a good fit, we scheduled a call. If the call went well, we scheduled an in-person interview.

We looked for strength in three areas:

Visual Design

The work in a candidate’s portfolio illustrates their understanding of composition, visual hierarchy, grid systems, typography, etc. However, beautiful visual design can mislead. Many good visual designers don’t possess the necessary user experience abilities for a product design role.

Interaction Design

Articulation of design flows and interactions shows a candidate’s competence in interaction design. I love hearing about the tradeoffs designers make, and how they collaborate with engineers to deliver a user experience.

User Research

Understanding how user research fits into the design process, and when to employ different methodologies is a mandatory skill for a Flexport product designer. The candidate doesn’t have to be an expert, but we require a general aptitude.

It is hard to find people with the these qualities, as well as the enthusiasm to learn the complexities of international trade.

After two new product designers joined, the complexities of my job evolved. I had to balance design projects with people management and career development.

We soon realized the limitation of a centralized design team. Designers felt like they didn’t have a seat at the table because they missed the many small decisions made between engineers and PMs. Engineers and PMs felt they didn’t have a single point of contact on the design team to guide these decisions.

Decentralizing Product Design

To mitigate the issues of centralization, we assigned each product designer to a product team. The product designer sat next to their product team, attended their meetings, and took design ownership of their projects. This solved our collaboration issues and increased output.

During this time, we defined a new user research role to aid the product designers in conducting foundational and continuing research. We also began to focus heavily on our UI system to ensure consistency.

The big missing piece of the team was communication design. Up until this point our marketing materials, brand identity, public websites, etc., were a secondary priority. Kaye and I dedicated a few hours a week to updating Flexport’s visual identity, and we worked with outside contractors to manage the workload. But without a singular focus, our brand identity suffered.

To fix this problem we brought on a communication designer to take ownership of our brand identity. During this time, we also decentralized the design team’s UI system function, partnering Kaye with other engineers to further develop our front-end architecture.

We also solidified our team meetings. We currently come together 4 times a week. Once on Monday for our design standup, on Tuesday and Thursday for critique, and on Friday for our retrospective.

Team Meetings

Weekly standup

Every Monday starts with a design standup. Everyone on the design team states what they accomplished last week, what they are working on this week, and any challenges in their way. This meeting provides accountability and transparency to the team. It reduces duplication of work and increases collaboration.

Design Critique

The design team comes together at the end of the day on Tuesday and Thursday for critique. We often invite engineers, PMs, and other stakeholders. We schedule who is going to present work beforehand. Before the work is shown, the presenter provides the context of the project, the fidelity of the design, and the questions they want answered. This provides focus so we don’t go on tangents that aren’t important to the context of the work.

1:1s

I formally meet with each designer once a week. It is a place for the designer to vent any frustrations, as well as talk about their successes. It is also a mini two-way performance review. It’s much more constructive to provide feedback early and often instead of letting things come our quarterly or annually. It allows many small course corrections as we work to create a healthy design team. It is also the time to brainstorm career growth. Each designer on the team has unique strengths and weaknesses. Having a clear understanding of your competencies and development plan is invaluable.

Office Hours

As a manager, it is not surprising to have back to back meetings for the majority of the week. This is why I block off an hour and a half on my calendar every Thursday. The time is open for designers, product managers, and engineer managers to discuss pressing issues and tactical work.

Weekly Retrospective

The week adjourns with a retrospective where each designer announces what they accomplished, the frustrations they encountered, and ideas on how to improve the health of the team. The meeting also serves as a way for the team to bond. We often go out for dinner or drinks during this time.

We laid a solid foundation to further the design team’s growth, and we have a long way to go. It will take lots of perseverance, flexibility, and a growth mindset to get to the next level. I have no doubt we will attain it because of the amazing team we assembled including:

Becca Ling, Product Designer

Becca possesses the ability to beautifully visualize complex datasets in an accessible way. As an early employee at 23andMe, she did amazing work designing how people interact and understand information. We are lucky to have her on the team.

Quintin Carlson, User Research Program Manager

Quintin transitioned from a product designer to a user researcher after we realized his rare ability to attain deep empathy with our diverse users. The insights he distills from the countless user interviews and contextual analysis he conducts influences the team’s design decisions, and often form the foundation of new initiatives.

Andrew Kaye, UI System Lead

Kaye has a history of combining art with technology to solve problems. He received an MFA from the prestigious SAIC, where he later taught. At Flexport he is our unicorn designer, possessing the ability to translate his (and other’s) designs into code.

Gentian Edwards, Product Designer

Gentian has a mastery of visual and interaction design. She cuts to the heart of complex problems, creating beautiful design solutions. She does this while constantly refining her processes and methods. There is always a better way. This attitude makes her a powerful force on the team.

Eytan Davidovits, Product Designer

No matter the project — big or small, complex or straightforward — Eytan delivers with meticulous detail and clarity. He is not afraid to collaborate with others to discover the right solution, and he can make sense of any situation.

Seth Gutiérrez, Communication Designer

Seth is one of the most talented graphic designers I have had the privilege to work with. He was previously at Box where he helped define their visual brand identity. He now has the responsibility of taking ownership of Flexport’s brand aesthetic. His deep understanding of design principles and ability to execute on a wide range of projects is indispensable.

From Individual Contributor to Manager

I enjoy looking back at how different my job was as an individual contributor. As the design team grew, the less individual contributor work I did. Now, as the director of design, my work includes:

Hiring

• Screening candidates
• Conducting phone and in-person interviews
• Reaching out and meeting potential candidates

Team Management

• Weekly 1:1 meetings
• Performance reviews
• Conflict resolution

Design Direction

• Critiquing each designers work
• Illustrating a vision for the future
• Creating design systems

Team Operations

• Work Prioritization
• Weekly standup, team critique, and other structural meetings
• Working on messy design projects

The most important thing I have learned in my transition from an IC to a manager is the power of delegating responsibility, listening, mitigating conflict, and spurring collaboration between roles.

There is a lot to learn. This is just the beginning. If you would like to play a role in further defining our culture and solving problems that effect the real world, Join us!

I hope this article helps you design a better design team. If you are currently leading a team, or are planning to build one, I would love to hear your thoughts.

Books that helped me build and lead a design team:

To learn more about Flexport read:

CNN: How to get 60,000 containers around the world in record time