The self-service Tax Organizer intake flow, live in the client portal.

The self-service Tax Organizer intake flow, live in the client portal

TaxRise

Replacing a 15-day manual process with a self-service form

Over 40% of TaxRise clients had multiple unfiled tax years. Collecting what was needed took 15 to 20 days per client: phone calls, faxes, and unsorted document uploads. I designed a structured self-service intake tool to replace all of it.

ProblemBefore TaxRise could resolve a client's tax debt, every unfiled year had to be filed. The average affected client had 4 to 5 unfiled years.
OutcomeThe projected impact was based on what the workflow changes would eliminate: 15 to 20 days of back-and-forth replaced with a self-guided form, unsorted document uploads replaced with structured year-by-year collection, and intake capacity no longer tied to rep headcount.
RoleLead Product Designer
Timeline2022 · 2 months
PlatformWeb (Desktop)
50%+Projected reduction in intake time
15-20 daysExisting intake time per client
40%+Of clients affected by unfiled years

MY ROLE

Lead designer, discovery through handoff

I drove the design from discovery through final handoff. I worked directly with the CEO, the lead tax professional, a Salesforce consultant, and the lead developer. The project had been flagged as a priority by leadership.

THE PROBLEM

A manual process at scale

Before TaxRise could resolve a client's tax debt, every unfiled year had to be filed. The average affected client had 4 to 5 unfiled years. To gather the information needed, clients mailed documents, sent faxes, dropped things off in person, or went back and forth with a case manager over the phone, often without the documents they actually needed.

The intake process took 15 to 20 days per client. Reps were stretched across high case volumes. Scanned documents came in illegible or incomplete. There was no way for clients to see what they'd submitted, what was missing, or where things stood. Resolution couldn't start until intake was done, which meant the entire business pipeline was gated behind this bottleneck.

Resolution could not begin until every unfiled year was filed. So this one intake step gated the entire business, not a single team's workload.

Diagram comparing the manual multi-channel intake process to the self-service Tax Organizer form.

Manual multi-channel intake, replaced by a self-service form

"Our goal is to digitize an industry stuck in history."

Sam A., Founder & CEO

DISCOVERY

Learning the domain first

I started by studying how TurboTax, H&R Block, and FreeTaxUSA handled single-year filing. Not because we were building that, but to understand how the best products in the space structured the question flow. None of them dealt with multi-year filing, which was the core problem we were solving.

Time with in-house CPAs and case managers filled in what the competitive analysis couldn't. They'd done this intake hundreds of times and knew exactly which questions tripped clients up, what data was actually needed per year, and where the existing process fell apart.

The biggest design constraint coming out of discovery: the average TaxRise client had no tax literacy. They didn't know what a W-2 was, couldn't tell a 1098 from a 1099, and didn't understand the difference between state and federal filing. Everything had to be designed around that baseline.

Zero tax knowledge~50 years oldLow tech comfort4 to 5 unfiled years40%+ of the client base affected
Client portal information architecture

Tax Organizer placement within the client portal

KEY DECISION: CARRY-FORWARD

Solving for four years of the same questions

The average client had four to five unfiled years, and some had ten. Most of what the IRS needs for one year is identical to the year before it. The design question was how to collect ten years of tax data without asking someone with no tax knowledge to answer the same forty questions ten times.

Year by year

Explored, rejected

How it worksComplete a full set of questions for each unfiled year, one year at a time
What it asks of the clientEvery question, every year. Roughly the same answers repeated four to ten times
Where it breaksClients abandon partway through, or start guessing to get to the end
WhySimple to build and simple to understand, but it treated a client's time as free

Carry-forward

Chosen

How it worksComplete the most recent year in full, then confirm at each section which other years match
What it asks of the clientThe full set once, then a yes or no per section for the remaining years
Where it breaksRequires clear checkpoints, or a client can carry forward something that actually changed
WhyCut total inputs sharply while still capturing the years that genuinely differ

I started with the most recent year rather than the oldest for two reasons. Recall is better for the year a client just lived through, so the first and most detailed pass is also the most accurate one. And the most recent year is the likeliest to resemble the years next to it, which means the carry-forward is doing the most work when it's most reliable.

Carry-forward checkpoint

Carry-forward checkpoint applied at the end of each section

KEY DECISION: PLAIN LANGUAGE

Plain language over tax terminology

Instead of asking clients to identify document types, the form asked about situations.

Do you have a 1098-T?Did you pay for school?
Do you have a 1099-G?Did you receive unemployment?

The system matched their answers to the right tax forms in the background.

The year select screen showed every unfiled year with a clear status. Clients could see their full scope upfront and track progress as they moved through it. For a process that could easily feel like it had no end, that visibility mattered.

Not startedIn progressSubmitted
Plain-language question flow

Plain-language questions mapped to IRS forms behind the scenes

CONSTRAINTS

Designing for handoff from the start

Developer turnover was a constant on this project. Designs had to be documented clearly enough that someone new could pick them up cold. The tax team kept refining what data they actually needed, which meant requirements shifted regularly. The form also had to handle:

State vs. federal differencesMultiple document categoriesClient-specific tax situations per unfiled year

All without becoming a system too complex for a non-technical client to navigate.

IMPACT

Handed off, not yet shipped

The projected impact was based on what the workflow changes would eliminate:

15 to 20 days of back-and-forthA self-guided form
Unsorted document uploadsStructured year-by-year collection
Intake capacity tied to rep headcountNo longer tied to headcount

I completed design and handoff over roughly 2 months and left TaxRise before the Tax Organizer was built and deployed.

The carry-forward system was the part I was most confident in. It's the kind of decision that doesn't show up in a static screen. For a client with five unfiled years, it can be the difference between completing the process and giving up.

REFLECTION

What I learned

I validated with experts when the whole design was built for novices

The core premise was that the average client has zero tax knowledge. I tested with CPAs and case managers, because they were available and I was moving fast. They're the wrong proxy almost by definition. Every plain-language decision I made was reviewed by someone who could read the jargon fine, and I never got to watch a real client hit a checkpoint and hesitate.

Carry-forward came out of the domain, not the interface

I didn't find that pattern by sketching. I found it reading IRS Forms 433-A and 1080 and listening to case managers describe what a four-year filing actually looks like, which is mostly the same answers over and over with a few real differences. Starting with the most recent year and asking which other years match reduced the inputs dramatically. The interface was downstream of understanding the paperwork.

Designing for a build I wouldn't be there for

Developer turnover was constant and I left before this shipped. That forced a different standard for specs: every state documented, every edge case named, no decisions living only in my head or in a Slack thread. It's the least fun part of the job and it's the part that determines whether the work survives you. I still design to that standard when I don't have to.