Identifying the pain points of a scary process to ease anxiety and build trust.

Henry.tax is a project of a New York City-based accounting firm that approached Objective Subject with an idea: pair tax prep customers with CPAs via a digital portal. The client engaged Objective Subject to design the responsive website that would facilitate this interaction. I guided the User Research, Information Architecture, and UX Design phases of the project, and partnered with another designer for UI.

Website: henry.tax
Date: Fall 2017


Our client had an idea: a tax service that pairs CPAs with tax prep customers via a digital portal. While they had a general sense of the product’s contours, they asked us to think through the UX and flesh out the UI of their idea.

The service had the potential to hit a sweet spot—the peace of mind of professional tax preparation for a much lower price than hiring a personal accountant—but the product would never get off the ground if we couldn’t convince customers that the product was reputable and secure. Furthermore, we wouldn’t retain customers if a poorly-designed product added more stress to an already stressful process.


Customer Journey Map

In a sense, our most important user need was already defined: a gap in the market that would help people get expert tax prep for less. But we needed to undertake another layer of research to understand how to win customers’ trust, and then to make a daunting process—taxes—less scary for them.

We designed a UX process to help ourselves understand the tax process as well as filers’ emotions about it—where it causes the most anxiety, and how our product could mitigate that. Taxes are a scary process with many pain points that needed to be identified and designed for. We started with a deep research dive into the tax process itself: who files, what they file, how documents are passed back and forth, etc. (of course, we had some anecdotal experience here). Then we turned to users, conducing informal interviews with prospective customers referred to us via the client to understand how their frustrations filing taxes year in and year out might inform our product.

Informed by our research and customer insights, we drafted a Customer Journey Map to plot a preliminary product flows alongside universal pain points—where users have anxiety about taxes, or might have anxiety navigating our product. We then brainstormed product opportunities that might mitigate anxiety for the “low” points of our journey’s user satisfaction. For instance, while the complex nature of taxes require a long sign-up process, users might abandon the product entirely if asked to submit too much personal information before trusting the product. So we incorporated a ‘skip’ option for all onboarding that would allow users a peek at the primary dashboard before committing (or fishing out a credit card). This process also helped us identify where to use progress indicators and friendly copy to reassure customers—for instance, that uploaded documents had been saved.

Service Map

We also did a Service Map to understand flow and communication between parties—CPA, Customer, and Henry.tax Admin. One revelation that came out of the Service Map process: with so many parties communicating, simple back-and-forth email wouldn’t suffice. We needed an additive message thread that would give anyone viewing the thread a quick snapshot of all prior correspondence. After exploring precedents, we settled on an Airbnb-esque message interface, which bundles all messages and documents in one reverse-chronological thread.

Together, the Customer Journey Map and Service Map informed a robust wireframing process, which helped us iterate and make product decisions with the client. From this back and forth the full process emerged:

(1) Create Account, (2) Profile & Billing Info, (3) Income, (4) Deductions, (5) Credits, (6) Summary & Questions, (7)Accountant Working, (8) Ready for Review, (9) e-Filed

We put an InVision prototype in front of users, asked them to perform basic tasks, which helped us validate our assumptions and refine where necessary. While I continued to adjust the product in wireframe, another designer pushed the visual design.


Henry.tax makes a good first impression, then anticipates user emotions as they navigate a complex process. The site pulls off a careful balance between utility and whimsy.

A bold marketing page doubles as homepage, leading off with benefits of the product and then walking skeptical potential customers through the Henry process with cute animations. A big call-to-action leads to smart onboarding that allows users to opt-out of any given step to jump straight into the functional dashboard.

While the visual design and copy of Henry.tax are approachable—almost playful—the interface and interaction design imply that the portal is a serious tool. The left rail is intended to evoke utility sites like Dropbox and Google Drive—the steps of the document upload process clearly mapped out and color-coded according to level of completion to give anxious customers a snapshot of where they are in the overall process. Drag-and-drop interactions feel intuitive and ease the document transfer process. Status indicators after each step reassure users that whatever they’ve typed or uploaded is saved and secure.

No matter how good the UI or interactions, a product this complex invariably requires some human-to-human communication. It’s always easy to ask your CPA a question at any point, and messages and documents are conveniently bundled to know what happened when.

While not all of our recommendations made it into the product this year, the rigorous UX process we undertook helped the product achieve a successful launch, establishing a foundation that can be progressively iterated upon for future tax years.