Choosing your next opportunity in design: How to find a great fit

Will Tsui
Gusto Design
Published in
5 min readDec 20, 2021

With holiday season upon us, it’s a great time to take a step back, reflect on the year, and think about the future. If you’re re-evaluating your design career, there are more opportunities than ever and it can be hard to figure out where to start. Here are six things to keep in mind as you seek your next opportunity in design:

Values and culture

This can sometimes be hard to assess from the outside, so don’t be afraid to ask questions about this during initial interviews at a company. What are the company values and how does this show up day-to-day? How has the company made diversity and inclusion a priority? Understanding how the team or company has responded to challenges they’ve faced can also be a good signal of their values.

At Gusto, our values include service mindset, ownership mentality, working with integrity, and building with humility. One example of these values in practice is the way we’ve served our small business customers by building tools to help them navigate the pandemic. As a company we also set meaningful diversity goals and hold ourselves accountable to making progress.

Stage of the company

The company’s stage of growth will influence the shape of design roles as well as many aspects of what it’s like to work there. Early-stage startups often require wearing lots of hats, which can be a great learning opportunity, but there will be fewer designers to collaborate with and learn from. Large companies often have well-defined design roles with more established learning and development programs.

Ask about how the design team has grown over time and what the anticipated growth is in the coming year. Faster team growth often means individuals have more opportunity for growing their careers by taking on larger responsibilities.

At Gusto, our design team is a group of nearly 60 designers, writers, researchers, and ops practitioners. We collaborate closely as a team through critiques and pairing sessions, and facilitate learning and development through our mentorship program. New career growth opportunities are frequently opening up as we scale to solve more problems for our small business customers.

Role of design

Across companies there’s an enormous spectrum of how mature design is as a function. At the best companies, design is leveraged to its full potential and has a big influence on strategy, products, and services. Some questions to ask that can help you understand better the role of design at a company: Why is design strategically important for the business’s success? Do the company’s customers care about great design? Do company leaders value and understand design? How is design positioned in the organization?

At Gusto, design is highly valued by both customers and company leaders. Gusto helps small businesses take care of payroll, benefits, and HR, and great design is key in making these complex problems simple for business owners to solve. Gusto Design has had a strong presence and voice since the earliest days: The first employee at Gusto was a designer, and today we have a Chief Design Officer, Amy Thibodeau, who represents design as part of Gusto’s executive team. Design has been a key partner in defining how we work and collaborate inside the company.

Remote work culture

Companies and teams have radically evolved over the past two years due to the pandemic. Many design roles are now remote or open to remote. If you’re looking for a remote role, you’ll want to be part of a culture that treats remote workers as first-class citizens. Ask about the geographic distribution of the team and how the team approaches collaboration in a way that’s inclusive of remote workers.

At Gusto, we’ve embraced a remote-first approach to collaboration, with many team members fully remote across North America. All of our design team rituals are remote-friendly, including critiques where everyone follows along in Figma, and virtual events to get inspired and connect as a team. A couple of my favorite recent events: A guest speaker, Jen Delos Reyes, who shared about her journey as a community arts organizer and urban farmer, and an interactive magic show where we learned tricks for making magic at home!

Career pathing

Some teams have fixed models for how designers can grow in their careers. This can create a challenge where the only way to advance one’s career is by going into management. Many design teams value individual contributors (ICs) as much as managers and have well-defined career paths for both. Often these teams are supportive of individuals moving from one path to another, such as a manager moving into an IC role, or a content designer moving into a design management role.

At Gusto, management and individual contributor roles are valued equally–even at senior levels–and our career leveling is designed to reflect this. There are many examples of individuals changing roles–both IC designers becoming design managers, as well as design managers becoming IC designers. There are also individuals in hybrid, player-coach roles that lead small teams as well as drive impactful IC projects.

Mission and impact

Tech companies are known for lofty mission statements. Seek to understand the real impact the company is having on society. Who is it helping? Are there ways the company is having a negative impact? How focused is the company on its social impact? If you’re not inspired by the company’s impact, you’re unlikely to find the work fulfilling.

At Gusto, we’re focused on helping small businesses and their teams. Our mission is based on three pillars: giving peace of mind, creating great places to work, and enabling personal prosperity. We see our social impact through stories from our customers about how Gusto has helped them and their teams thrive. One recent story is from a healthcare startup that was able to scale quickly on Gusto to provide in-home nursing care during the pandemic.

We hope you find these considerations helpful as you think about your next opportunity in design, whether that’s in the New Year or farther in the future!

Interested in learning more about Gusto Design? We’re hiring!

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