“One of Justin’s standout strengths is building strong design teams. He put in place clear career paths and promotion criteria that led to multiple promotions across both management and IC tracks. He’s got a great eye for talent and knows how to develop designers to do their best work.”
– James Aylward, CPO TPT
Building teams is one of the aspects of my career I’m most passionate about.
Throughout my career, I’ve had the privilege of being the first or second designer at an organization, just before a period of rapid growth. This early-stage involvement offers a unique set of challenges and opportunities, particularly when it comes to scaling a design function and building a design team from the ground up. At both Vimeo and TPT, I’ve grown teams from just a few generalist designers into dynamic, specialized teams of 11-15 designers focused on various aspects like product design, branding, and marketing.
The Challenges of Growing a Small Design Team
When starting a design team from scratch, organizations face several key challenges. One of the primary difficulties is balancing the need for generalist skills with the desire for specialization. In the early stages, you often need designers who are versatile and can handle a wide range of tasks. But as the team grows and the demands on design become more complex, you need to transition to specialists who can deeply focus on different areas such as product design, UI/UX, user research, and branding.
This is a delicate balancing act. Hiring too many generalists too quickly can result in a team that lacks the depth needed to execute at a higher level. But hiring specialists too early can lead to gaps in skills or an oversupply of talent in one area while other disciplines are neglected. It’s crucial to be strategic about the timing and type of hires you make.
Another challenge that comes with building a design team is ensuring the team is diverse—not just in terms of background and experience but in skill sets. In my experience, finding designers who bring different perspectives and strengths to the table can be difficult, especially when competing against larger organizations that already have established teams. I’ve learned that being very clear about what’s missing in the team and what’s needed for the future of the company can help me make the right hires.
Recruiting and Retaining Talent
Hiring designers is one of the most critical aspects of scaling a team, but it’s also one of the most challenging. The competition for top talent is fierce, and when you’re hiring for a growing team, every new hire has a significant impact on the team dynamic. One bad hire can affect morale and disrupt the work culture you’ve spent time establishing. This is why it’s essential to hire not just for skill, but also for potential and fit within the culture.
I’ve found that the most successful hires are those who are not only experts in their craft but also have a strong desire to grow. These designers are typically more adaptable, take ownership of their work, and are motivated by the challenge of making a significant impact.
But even after hiring great talent, the challenge doesn’t end there. Retaining designers requires creating an environment where they feel valued, where there is room for personal and professional growth, and where they have clear goals for their career progression. At TPT, I developed clear career paths and promotion criteria, modeled after Radford levels, to help guide designers at all levels. This structured approach provided transparency around career advancement, allowing designers to clearly understand what was required to move up and how they could achieve their goals. This clarity played a significant role in retention, as designers could see a path forward within the company.
Establishing Strong Design Leadership
As the design team grows, the need for leadership becomes more critical. Design leadership is not just about overseeing the execution of design work—it’s about setting the tone for the team, fostering a creative and collaborative environment, and ensuring alignment between design and business objectives. One of the challenges of growing a small design team is figuring out how to instill strong leadership without having an established management structure.
When building the team, I made it a point to implement clear processes and expectations from the very beginning. These structures helped us scale effectively and ensured that as we brought in new people, they understood their roles and how their work contributed to the overall vision.
For me, leadership also means mentorship. As I hired talented designers, I took on the responsibility of mentoring each one, providing them with opportunities to take on more responsibility and grow within the organization. Over time, I’ve developed a system that helps designers at all stages of their careers understand where they are, where they’re going, and how to get there. This system has become instrumental in the growth of both individuals and the team as a whole.
Managing Growth and Team Culture
Growing a design team comes with its own set of cultural challenges. Early on, the team is small, which makes it easier to maintain a tight-knit, collaborative culture. But as the team grows, it’s easy to lose that sense of intimacy and cohesiveness. Maintaining strong communication and alignment across multiple designers, especially when they are working on different products or projects, becomes more difficult. Ensuring that everyone is on the same page and that there’s a shared vision becomes a priority.
One of the strategies I’ve implemented to address this is fostering a collaborative environment through regular check-ins, team-building activities, and design workshops. These aren’t just ways to help improve specific skills but also provide space for the team to bond and align on a shared vision.
Regular 1:1s with each team member are also a crucial part of my approach. These meetings aren’t just about project updates; they’re about providing individualized support, setting personal goals, and ensuring that each designer feels like they have a stake in the team’s success. By fostering a culture of transparency, feedback, and mutual support, I’ve been able to create an environment where designers feel motivated and excited to contribute.
The Evolution of My Managerial Process
As the team has grown, I’ve evolved my management style. Initially, I relied heavily on individual mentorship and informal feedback, but as the team expanded, I realized the need for more structured processes. Over time, I developed frameworks for 1:1 meetings, goal-setting, and performance reviews that helped me stay aligned with each designer’s development path while also ensuring that the team as a whole remained on track.
I also implemented workshops and regular team retrospectives to ensure that the team could reflect on its successes and challenges, helping us continuously improve our processes and outputs. These initiatives have proven to be invaluable in maintaining a high level of engagement and productivity within the team.
The Long-Term Impact of Design Leadership
At the heart of it, my passion for building teams comes from the belief that great design can have a profound impact on business success. As I continue to grow teams, I’m focused not only on the immediate output but on creating sustainable, scalable systems that will continue to serve the team as it grows and evolves.
Whether it’s managing hiring budgets, advocating for additional headcount, or creating clear promotion pathways using systems like Radford levels, my approach is always grounded in the long-term success of the team and the business. I’ve seen the difference a strong design team can make in driving innovation, improving product experiences, and shaping a brand’s identity.
Ultimately, building and mentoring design teams is not just a responsibility for me—it’s a passion. I’m committed to ensuring that every designer I work with has the resources, guidance, and support they need to succeed in their careers and contribute to the broader success of the organization.
Building a design team?
I’m available for consultation, contract, or full-time work.
Justin Dickinson 