The UX practice for insurance & embedded protection

Insurance products can be fraught with UX issues: a claims process that leaves the user confused, incomplete digital solutions that drive up calls to support centers, or misleading information on your site that can lead to regulatory exposure. I dive deep into the specifics to make sure your platforms are built with a comprehensive focus on the user.

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

Book a Call See the work ↓

Sam Eastham Book a Call

Why insurance

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

In my time working in insurance, I’ve noticed that UX continues to lag behind. Yes, there are some newer services that claim to offer a more design-forward experience, like Lemonade, but even 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 affordances users need to fully understand what’s covered before purchasing the policy in the first place.

That’s where I come in. I’ve spent over 12 years in enterprise UX, with five working in claims systems, frontend and backend. Over the course of my career, I’ve enjoyed working on fine-tuning the design of insurance systems to deliver a robust, user-centered experience with proven results. Creating simple and intuitive resolution pathways, for example, leads to greater de-escalation of disputes. 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. 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. From refining the purchase journey to streamlining workflows for your service reps, I will ensure you’re delivering a holistic, user-centered product that accounts for the deep specifics that bring a claims flow from usable to seamless.

FIG. 01 SHARED TIMELINE QUEUE EXCEPTION SUMMARY ▮▮▮▯
FIG. 01 — Claims systems, consolidated. On the left, independent APIs from separate and legacy systems feed into the unified view for the user. Dates and actions pulled from these separate sources are combined into the shared timeline at the top. 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

Different levels to match your UX needs and budget.

Whether you need an expert review of what you offer today, or you’re in the middle of a project that demands a seamless experience, I’ll provide the level of service you need, with options to fit different budgets. 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 keeps me at your disposal to keep your project on track. And if you need someone working directly alongside your team week by week, embedded work is available for intensive 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: it improves the experience directly, and it increases your bottom line through reduced costs and regulatory risks. The audit offers a meticulous examination of every aspect of your most important user flow. The audit report also includes a guide for UX metrics along with the changes you can expect after implementing the recommendations. If you aren’t tracking analytics, I will explain how to implement them as a part of the report.

The deliverable

A document detailing the results of the audit: highlights and top wins shown first, with a comprehensive breakdown of each finding and recommendation within, including the issue, category, explanation of its impact, suggested remedy, and analytics to measure improvement.

Includes screenshots, example code snippets illustrating a fix, and any applicable accessibility or UX heuristic violations. The document can be anywhere from 25 to 80+ pages 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
  • Your 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

Once the audit is finished, I will hold a 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. I will also make sure you’re positioned to measure the impact of the recommendations through analytics.

You get:

  • An end-to-end document: 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 and disclosure create 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

If your senior designers are at capacity on other projects, or if they stall on insurance-related questions, the retainer provides expert guidance to unblock your team and keep the momentum moving in the right direction. The retainer is a great option for those who are looking to avoid expensive mistakes and make informed decisions, without needlessly paying for an extra person to sit through 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, with the reasoning written out.
  • Recommendations based on UX standards, accessibility guidelines and regulations, and any usability research your team has performed.
  • A weekly 1-hour call to work through your most pressing issues with the team members 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 additional help with a project that has an end date, or if your design workload increased mid-project. Great for teams who currently need design leadership to manage a new design hire, or if you 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 work with the engineers to execute 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.
  • Documentation 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 once my work is coming to a close.
  • Three-month minimum commitment, 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 user centered design work, and it’s where my focus in insurance lies: 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.

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 judgment 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 doesn’t provide is a professional’s empathy, intuition, and ability to make sound judgment 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 without oversight in 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.

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
FIG. 03 — One summary, three confidence states. A drawing of an interface, not a working one. Nothing in it is clickable. Fictional data throughout.

How I’ve shipped this →

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, can make or break the UX integrity of your product.

About

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 knew that “user error” often means that the system 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’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.

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 could perform better in your product.