Designing a Better Underwriting Experience: Q&A with Sean Singleton

Steve McOrmond
March 24, 2023

As Head of Product Design at Federato, Sean Singleton and his team work closely with software development, product management, and most importantly, our clients to design a better, more efficient, and intuitive underwriting experience from the ground up. We sat down with Sean to ask a few questions about Federato’s unique design methodology and approach to solving difficult problems. Sean shares insights from his 20+ year career in design, and discusses why starting from first principles – and focusing on people and the problems they encounter in their day-to-day work – is the only way to address underwriting and portfolio management challenges that have plagued the insurance industry for far too long.

Sean, in their recent Design Issue, the MIT Technology Review asks the question, “If everything is design, is anything?” In your own words, what is your definition of ‘design’ as it relates to developing software products like Federato’s RiskOps underwriting platform?

As my career has evolved, my approach and my definition of design has also evolved. Our responsibilities as designers goes beyond what users see on the screen, beyond the things that make a product visually appealing. And now, especially as it relates to design for digital products, our responsibility is really about designing experiences the customer’s overall experience with the product, from beginning to end.

Tim Brown, CEO of IDEO, one of the world’s leading global design firms, believes that “Innovation is not about ideas, it's about solving problems.” One of Federato’s core values is, “Businesses don’t have problems, people do.” Can you share a bit about Federato’s design-driven approach to solving hard problems for our insurance clients?

I thought this was a brilliant characterization of Federato’s approach to solving problems for our customers. We sell our product to businesses but, ultimately, we build the product to provide a solution to users. I adopted a user centered approach to design back in the early 2000s, and as the design industry has matured, designing for the needs of the user has become core to our role as designers. At Federato, our design and product team is fortunate to not only have people with career experience in the roles we are designing for who we can turn to for understanding underwriters’ needs, but we are fortunate to have customers who are always willing to offer their time to do user interviews and feedback sessions. So we are constantly building on our understanding of underwriters’ needs and our knowledge of the industry as well. This translates into more informed design decisions as we build and refine features within our platform.

The design team at Federato conducts 3-5 hours of user interviews and hands-on workshops each week. Can you walk us through the process, and how you and your team use customer feedback in the product design process?

As I mentioned, we have former underwriters and insurance industry professionals on our staff, and we have great relationships with our customers who are always willing to partner with us to make the platform better. This makes scheduling user interviews and feedback sessions easy. We usually try to have someone from Customer Success, Product, and Design on calls regarding user interviews for discovery, but oftentimes we may just want to validate a design, interaction or workflow, and in those cases, a product designer may facilitate a call on their own. The designers on our team are enthusiastic about putting effort into user research, and utilizing that information to guide their design solutions.

“We try to gear our questions to really dial in to uncovering the users’ pain points in existing solutions and to avoid creating pain points in features we are planning before they get into production.”

– Sean Singleton, Head of Product Design, Federato

Ok, so you’re meeting with a client and the colored sticky notes and markers – or their digital equivalent, the Miro board – come out. How do clients typically react? Is there skepticism at first from folks who may not be too familiar with design methodology, and what’s the feedback like following a session?

There are typically a range of reactions to the tools and methods themselves. More companies are remote and utilize some of those same tools, so I think a lot of our clients and their teams are used to most of the tools we use. For those that aren’t as familiar, I think they really trust us to guide them through the process. 

“Most often they are focused on the end goal, and really all we need to do is assure them that these sessions are a critical step in the path to providing them with solutions for their pain points.”

– Sean Singleton

Most often, the reaction and the sentiment we hear after a design session or a group user interview is the realization and relief that we are serious about really understanding their problems, not just trying to sell them software.

Part of the process involves closely observing human behavior as underwriters and staff interact with data and tools in order to gain a deeper understanding of how they really think, and what matters most to them. Can you tell us a bit about how you capture and record these behaviors and use them to build a better product?

When possible, we like to have users guide us through “a day in the life”, show us what their typical workflow is, just as they would typically navigate it on a day-to-day basis. We like to prepare a concise list of questions that guide the user to talk about their experience more than guide them to giving us a certain answer. This allows us to ask follow up questions to even further understand the responsibilities of their role, how they interact with data, and manage their processes online and offline. Our goal is to have a better understanding of their specific workflows and help us get closer to the root of the problems they face.

We record about 90% of our meetings with customers. This allows us to be really present during our calls with users, to pay attention to what they are doing and how they are doing it. The recordings allow us to replay the calls and pull out even more insights than we may have uncovered in the live session, and this assures the ability to share the information with the wider team (whom we consider all responsible for understanding UX needs). At this point, we have a growing library of thousands of hours of user interviews and design sessions that we can draw from – it’s an incredible resource for real-world insights on the underwriting experience.

Over your career, how have you seen product design change and evolve? 

I started my career in print and graphic design. When I transitioned to web design, we were still using Photoshop, basic tables, and css. Flash was just coming on to the scene. I think the rise of mobile apps, and the innovations and practices around mobile design heavily influenced how we started to approach designing software for the web and what has become SaaS. The unique technology of smartphones and the new interaction patterns they required forced designers to think more deeply about how users interact with our designs. The same thing happened when software applications started to move to the cloud. We had to think differently about how users interact with “web sites”. Eventually we — accurately — started to treat design for web apps differently than we would for a web site. Knowing that users were doing more than just reading a website and actually relying on web apps to aid them in completing work and accomplishing important tasks, the responsibilities and skill sets of web and UX designers transformed to serve different needs for our users.

What attracted you to Federato? What stood out about the Federato team, technology, or approach that made you want to join us on this journey? 

The things that factored into me joining Federato started with my initial conversations with Will Ross, our CEO and Co-Founder. Initially, my understanding of the potential impact this product could have in economic equality was intriguing, especially when I thought about the potential for the design challenges a product in this industry might pose. Next, there was a high premium placed on the importance of design and the impact it could have in building on the success of the product. It was an intentional and passionate objective for the company. The closer for me, though, was the support and belief in the potential of the company and the product that I heard when I had the opportunity to talk with one of our lead investors.

What’s one thing that people might be surprised to learn about you?

All of the skills I’ve developed related to UX and product design I’ve acquired through practical experience on the job or by researching and learning on my own. I studied graphic design in school and had no experience designing for the web when I started my first web-focused job with a startup in the Bay Area.

What do you consider your greatest achievement?

I think there’s still more stories to be written around great achievements. But I’d have to say, to this point, my greatest achievement is sustaining a career for over 20 years, doing something that builds off of a natural talent, and that allows me to go to work every day doing something I genuinely enjoy.

What’s your favorite thing to do when you’re not at work?

Cooking, watching sports (especially watching my kids play sports), dining and traveling.

Ok, bonus lightning round! Can you please answer these next few questions in one sentence or less. Some of these come from a parlor game popularized by French writer Marcel Proust, who believed a person’s answers would reveal his or her true nature.

First job and what, if anything, did it teach you about design?
My first official job was working at an Icee stand at the Santa Clara County Fair in San Jose, CA. I can’t say it taught me anything about design directly, but I did learn that people love Icees and pretzels — and Cherry was more popular than Blue Raspberry.

Favorite sport and team, and why!
Absolutely and unequivocally my favorite sport is football and my favorite team is the Denver Broncos. I grew up in Colorado and have been a fan since I was 7 and watched them (lose) in SuperBowl XII.

Last book you read?
I haven’t finished it yet, but as a company the book Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect by Will Guidara is recommended reading. We are adopting some of the concepts and philosophies from the book in our approach to providing the best products and services to our clients. 

Your most treasured possession, and why?
My Vestal ZR3 Platinum watch, I got it during a transition period in my life. Here’s a glowing review!

What’s your greatest extravagance?
Travel. It took me a long time to get comfortable spending money like that, but the experiences I’ve had traveling with family and friends so far have been worth it.

What do you consider the most overrated virtue?
I guess I’d say idealism. I think we can always aim for our ideal outcome or situation, but it's important to always be prepared to adapt to less than ideal circumstances.


More on the topic

See more