The UX practice for insurance & embedded protection

Insurance UX problems I’ve uncovered include issues like a confusing claims process, forcing the customer to call in rather than providing a digital solution, or misleading terms posted on the site. I dive deep into these and many other issues to make sure your solution’s design is built comprehensively, centered on the needs of the user and the business.

12 years in enterprise UX · In-house at Assurant · Enterprise design for a Fortune 50 telecom · US Central hours

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Sam Eastham Book a Call

Why insurance

Insurance holds an abundance of UX wins, but it needs expertise to uncover and implement them.

In my time working in insurance, I’ve noticed that it tends to be an oft-neglected industry in terms of usability. Yes, there are some newer services that purport to offer a more design-forward experience, like Lemonade, but I find that the experiences with polish tend to be a façade over the more gritty details—the edge cases, the points where a customer needs to speak to a rep, or the ability to actually have a good understanding of coverage before purchasing the policy in the first place.

During my career, I’ve enjoyed working on fine-tuning the design of insurance systems to fix exactly these kinds of issues. Disputes, for example, de-escalate when the process is simple and intuitive. Context is key for stressful edge cases. If a customer is in an area with poor signal, good UX makes sure that your app will still load for them when they need it most to file their claim. I’ve come to know where to look for these details by working through them over the years. My background will enable you to deliver a more holistic, user-centered product that accounts for the deep specifics that bring a claims flow from usable to seamless.

Specifically, I bring over 12 total years of experience in enterprise UX, with five working in claims systems, both front and backend. At Assurant, I designed and helped develop a claims system that unified an array of separate systems into one streamlined process and cut average call time in half. There have always been tremendous opportunities for improvement in these systems. From meeting SLAs and disclosure requirements, to keeping things consistent and intuitive, an optimized experience impacts both customers and employees and will bolster your bottom line.

The figure below shows a demonstration of bringing several different claims systems together under one unified application. Less uncertainty, more reliability, easier handoff between teams, improved SLA times, and a happier customer.

FIG. 01 SHARED TIMELINE QUEUE EXCEPTION SUMMARY ▮▮▮▯
FIG. 01 — Claims systems, consolidated. On the left, the independent APIs from previous systems feed into the unified view for the user. Dates and actions taken from the different systems are combined into the shared timeline at the top. Different symbols are used in addition to different colors for accessibility. An AI summary is implemented at the bottom so that the user can quickly determine what their most urgent action items are at a glance.

Services

Three engagements, each at a different level for different needs.

The audit is perfect if you know a specific user flow in your product needs particular attention to bring it up to the standards it should be meeting. The retainer makes more sense if you need an ongoing advisor to keep your project on track. And if you need someone working directly alongside your team week by week, embedded work is available for work that needs additional hands-on help.

FIG. 02 AUDIT ONE FLOW · EVERY STEP EXAMINED RETAINER EVERY FLOW · REVISITED ON A CADENCE EMBEDDED EVERY FLOW · ALONGSIDE, WEEK BY WEEK

The UX Audit

$5,000 flat · 2 weeks

A UX audit offers a double-win for your business: an improved user experience, and saving your bottom line in doing so. I will be meticulous in examining every aspect of your most important user flow to ensure optimized usability, and it will be reflected in the final report.

The report will also include expected improvements in the metrics your analytics provide and how to measure them. If you have no analytics implemented yet, I will explain how to implement them as a part of the report.

The deliverable

An end-to-end deck explaining the results after auditing your most important user flow. Highlights and top wins shown first, with a comprehensive breakdown of each finding and recommendation within, including the issue, category, explanation of the harm it’s doing, the suggested remedy, and analytics suggestions to measure the impact.

Includes screenshots, example code snippets illustrating a fix, and any applicable accessibility or UX heuristic violations. The deck can be anywhere from 25 to 80 slides long depending on the number of steps and issues in the flow.

What I need from you
  • Access to your full site flow, with login details if required
  • Design system & guidelines
  • A quick 30 minute discussion at the beginning of the audit to align on expectations.
  • A 90 minute meeting at the end of the audit to discuss recommendations.

What happens after the audit

Throughout my career, I’ve worked with development teams to bridge the gap between design and implementation. Additionally, as someone who has hand coded apps in the past, I understand what is and is not technologically feasible. Once the audit is finished, I will attend one 90 minute implementation session with your dev team to make sure that the recommendations from the audit don’t get lost in translation, with an eye toward how the recommendations will live in your codebase.

You get:

  • An end-to-end deck: highlights and top wins first, then every finding in full
  • A prioritized fix list, split into ship-this-quarter quick wins and structural work
  • Trust and compliance flags: where language, disclosure, or state variation creates risk
  • Three sessions — a 30-minute kickoff to align on expectations, a 90-minute meeting to walk the recommendations, and a 90-minute implementation session with your dev team

Set up a quick call here to get started.

Audit slots are open now. One audit slot at a time. For around the same price as a week of a senior designer’s loaded cost, and a fraction of an agency discovery phase. Read a published teardown →

Advisory retainer from $3,500/mo

For teams who already have capable designers, but who either stall on insurance questions, or are already at capacity on other projects. If your team needs answers, but doesn’t necessarily need more hands-on execution, then there’s no reason to buy hours that you won’t use. The retainer’s advantage is that it helps prevent expensive mistakes and unblocks decisions, without paying an extra person to sit in your daily standup.

You get:

  • Async access to me for the questions that stall your team, answered within one business day.
  • A design-review pass before anything ships: flows or screens flagged with any issues found, and with the reasoning written out.
  • Recommendations will be based on UX standards, accessibility guidelines and regulations, and any usability research your team has performed.
  • A weekly 1-hour call to work through whatever stalled hardest that week, with whoever on your team is closest to the problem.
  • Month-to-month coverage, with thirty days’ notice either direction. If you’re predicting a quiet stretch, request a pause with one call.

Read the operations console case study →

Embedded engagement from $12,000/mo

Limited availability

I can lend a hand if your team needs more help with work that has an end date, or with work that increases mid-project. Maybe your team lacks design leadership to manage a new design hire. Or, you just need help implementing the audit. For any of your projects that need an expert who can take responsibility for the UX, end-to-end, I’ll be part of your team, there to assist any junior designers, and to debate with the engineers about executing the design.

You get:

  • Kickoff within a week of signature.
  • One workstream owned end to end: problem definition, user flows, specs, and implementation support alongside your engineers until it ships.
  • Roughly two days a week inside your team.
  • When my work comes to a close, I will put together a handoff document explaining the findings discovered during my tenure, how to resume any work that needs continuing maintenance from your team, and ideas for future sprints on your roadmap.
  • Three-month minimum, rolling after.

Read the claims platform case study →

Contracting

This is a consultancy with a team of one, so you will be working with me directly. In the case of an audit, the contract will be for the duration of two weeks. Payment is 50% upfront / 50% on completion. For larger fixed-scope projects, 30–50% upfront, then milestone payments. Retainers invoiced monthly. Pausing an advisory retainer requires 30 days’ notice. Resuming will depend on availability. Standard MSA, insurance NDA welcome. A team of one means you will have my background working to your advantage and, because I take on a limited number of clients, attention focused on your corner of the industry.

Retainer seats are open now. I take a maximum of three retained clients.

Selected work

Samples of production work

Visuals are abstracted recreations with fictional data — client work stays confidential.

FIX LIST SHIP THIS QUARTER

Published teardown — Extend attach flow →

Even though both of these storefronts may have UX designers on staff, important and urgent UX issues still fell through the cracks on their production website.

CENTRALIZED WORKFLOW TEST · REVISE

Global Warranty — Assurant →

The same unification problem as the operations console above, solved inside Microsoft Dynamics CRM: several separate claims systems behind one interface used internally. Ran usability testing and iterative design within the platform’s constraints, cutting average call time in half.

Some additional projects I’ve worked on

Claim status Received → In review

White-label claims platform — Assurant

Claims experiences that telecom and device partners deploy under their own brand.

Schedule Applications Curriculum

Career-transformation platform — The Home Depot

One internal platform for applications, scheduling, curriculum, and role-based access — designed around personas and journeys for students, instructors, and administrators.

Consistency at scale Performance

Startup UX consulting — RealTheory

Engaged as an outside consultant for end-to-end product design. Built the company’s first design system, led the Sketch-to-Figma migration, and owned analytics from tool selection to feature-performance metrics.

“Sam worked with RealTheory for over a year, helping us translate complex product requirements into intuitive, well-designed user experiences… Sam was also a great collaborator — smart, thoughtful, and someone who worked extremely well with our team.”

Lawrence Guillory, Co-founder, RealTheory

AI in production

Shipping AI into your product? Design the trust layer first.

Implementing AI

Many insurers are implementing AI into quoting, claims triage, and service. As this groundbreaking technology continues to advance, the key design challenge moves toward building trustworthy human–AI interactions, especially around errors, human oversight, and justification of decisions these models make. This brings a slew of questions never before considered. How should confidence and uncertainty be communicated? What should be shown when the AI gets something wrong? When and how should a human take over? How should automated decisions be explained to policyholders and regulators?

That’s interaction design work, and it’s where I focus my ongoing research: oversight patterns, error and fallback states, and decision transparency in regulated flows. AI in insurance succeeds when the surrounding interaction design makes automated decisions understandable, accountable, and recoverable.

Confident ≥ 70% confidence

87% confidence

Customer reports accidental drop resulting in cracked screen and rear damage. External report confirms damage exceeds policy limit. Estimate generated for customer review.

Sources (5)
  • ↳ Claim record
  • ↳ Adjuster note
  • ↳ Customer statement
  • ↳ External report
  • ↳ Photos (3)
Take over this summary
Uncertain 30–69% confidence

42% confidence

Limited information about this claim. The summary may be incomplete or inaccurate.

Confidence is low because
  • Photos missing
  • External report not received
  • Statements are inconsistent
Sources (2)
  • ↳ Claim record
  • ↳ Adjuster note
Take over this summary
Unavailable Model unavailable

No summary generated

The source record is below, unchanged. Nothing is hidden while the model is down.

Write the summary
MODEL GENERATES SUMMARY HUMAN REVIEWS OR EDITS DECISION RECORDED
Even though AI can help expedite decisions, having human sign-off ensures that the common issues of hallucination, reasoning breakdown, or lack of true, nuanced judgement abilities don’t cause more issues than the AI is solving. Fictional data throughout.

How I’ve shipped this →

The need for human input

The latest innovation in AI has been its ability to iterate through its process and “reason.” While this has undoubtedly improved its output, this “reasoning” should not be equated to the judgement of a professional. AI is good at taking inputs and transforming them into standardized outputs, much the same way that a mathematical function works. This means we can now get rapid designs, iterations, working code, prototypes, and even technical design reviews (for example, checking contrast ratios) in a small fraction of the time that these used to take. What it lacks is a professional’s empathy, intuition, and ability to make sound judgement calls based on a holistic understanding of your product, the context in which it’s used, the goals of your company, and the development team implementing your backlog. This MIT Technology Review article goes more in depth. For this reason, AI should never be used alone for enterprise products. It is a tool that should be used in tandem with someone who has years of practice ideating, innovating, and using their creative spark and empathy to create the delightful experiences that drive customer satisfaction.

Teardowns and Research

Two teardowns I’ve published, posted below, demonstrate an important, overarching principle: any summary provided, whether generated by a human or by AI, is a trust surface that can make or break the UX integrity of your product.

About Sam

Portrait of Sam Eastham

I’ve been passionate about UX even before I knew the term for it—since I was young, I’ve had the idea in my head that many times, when “mistakes” are made by the user of the system, it’s the system that has failed—not the user. Once I learned about the field itself, I have loved bringing design wins to teams: increasing efficiency, saving money, reducing mistakes, and making the lives of the users better, all thanks to user centered design.

User experience is always on my mind—most recently, as an example, I was fascinated by the ergonomic design of the Ninja Creami while making my own ice cream. The Design of Everyday Things was my first UX book, and Don Norman is one of my heroes.

I studied Spanish in my free time after college, fell in love with it, and moved to Mexico, where I continued my studies for over two years. I am happy to perform user research in English or Spanish, and can collaborate with teams in either language as well. I am passionate about language, and will be meticulous in elevating the quality and standards of your copy in English, and help direct its translation, as part of your product’s UX.

I’ve always loved 80s-inspired concepts, and am a big fan of synthwave music. I thought it would be fun to bring that idea of past meets future to design, and created the Future Retro design system. We need more whimsy back in our products.

Book a Call

Not ready for a call, but still have questions?

I’m open for UX discussions any time via email. Send me your information and what you think might be underperforming in your product.