PROJECT
Redesigning a Dual-Sided AI Tax Platform
How I rearchitected a complete product experience, consumer and tax professional, as the sole designer at an AI-powered accounting startup.
Fintech
AI Product
B2B + B2C
0 to 1
cliff notes
Overview: As the sole designer at an AI-powered tax accounting startup, I led a complete redesign of a dual-sided platform serving both high-net-worth consumers and the tax professionals managing their returns, across two distinct user types simultaneously.
Challenge: An engineer-built MVP lacked the design language, information architecture, and trust signals needed to serve complex tax clients and professional advisors. Both sides of the platform needed to be rethought from scratch.
Solution: A comprehensive redesign of the full consumer and tax professional experience, anchored by a shared component library that enabled consistent, scalable UI across both platforms. AI was woven into every surface as the core mechanism for delivering value to both user types.
Impact: A complete, high-fidelity, handoff-ready redesign across every major workflow, both user types, and a full design system.
DATE
April 1-15 2026
MY ROLE
Lead Product Designer
TOOLS AND TECH
Figma
FigJam
Claude AI
Clickup
CORE TEAM
1 Product Designer
1 COO
2 Full Stack Engineers
1 ML Engineer
Business objectives
Connecting design to the business strategy
OLarry's core bet was that AI could provide value neither clients nor advisors would find on their own. That meant designing two distinct experiences around one shared intelligence layer, where every screen and flow had to earn trust and drive action.
Step 1: define the problem
Understanding what was broken on both sides
The engineer-built MVP had functionality, but not experience
Before designing anything, I needed to understand what was actually broken. The engineer-built MVP had core functionality, but it was designed for engineers, not users. There was no design language, no hierarchy between the two user types, and no mechanism to surface the AI value the product was built around.
User Problem
Consumers managing complex tax situations across multiple entities have no clear way to understand their tax picture or know what to do next. The tax professionals serving them lack the tools to manage a full client book efficiently, leaving both sides underserved by a platform that should be doing the heavy lifting for them.
Step 2: research and discovery
Two platforms, two mental models, one shared system underneath
Consumer
Uncertain, non-expert, time-poor
Needs clarity on their situation and a clear next step. AI should reduce any confusion.
Understand tax picture instantly
Directed, prioritized actions
Trust in their advisor
Tax Professional
Skeptical, expert, deadline-driven
Needs portfolio visibility, fast docs, and proactive signals. AI should augment judgment.
Season-level portfolio view
Automated document intake
Proactive client flags
Step 3: design strategy
The MVP had no navigation logic. I restructured both platforms from scratch around user intent.
The consumer nav was reorganized into three distinct groups based on what users are trying to do: understand their situation, take action, and manage their tax picture. The tax pro nav was organized around the advisor workflow lifecycle from prospecting to filing. Both platforms share one AI layer and one component library underneath.
Consumer IA decisions
Grouped by user intent: understand your situation, take action, manage your tax picture. The AI bar persists across all sections because it is always relevant.
Tax Pro IA decisions
Organized around the advisor workflow lifecycle. Prepare is the most complex section and gets its own sub-workflow: Gather, Review, Approve, File.
Step 4: collaboration
Building in Partnership With Engineering
Designing for a tax platform means the front end and back end are deeply connected. Before and throughout the design process, I worked closely with engineering to make sure nothing fell through the cracks.
Technical Requirements Review: I read through engineering's technical requirement documents to understand what data the backend needed to collect and how it had to be structured. This ensured the frontend was capturing the right information at the right time
Translating Backend Logic to the Front End: Tax data is complex under the hood. When information from the backend needed to be surfaced to consumers, I made sure it was displayed in a way that was clear and actionable, not just technically present
Pressure-Testing Ideas Early: Before moving into full designs, I ran concepts by engineering to identify feasibility issues early. This kept the design process moving without pivots later
The Problem:
No financial visibility: High-net-worth consumers filing complex returns had no way to understand their current tax situation, outstanding obligations, or expected outcomes
Minimal MVP foundation: The existing experience offered only a welcome banner and a document list, with no status indicators, financial context, or sense of progress
No AI value surface: There was no mechanism to surface AI-generated insights, leaving the product's core differentiator completely invisible to the end user
The Solution:
Client-centered dashboard architecture: Organized the dashboard around the four questions every client asks at the start of tax season, mapping each directly to a KPI card with year-over-year trend context
Prioritized action feed: Surfaced exactly what each client needs to act on next, with time estimates per task to reduce friction and set clear expectations
AI insights panel: Designed a dedicated panel that surfaces savings opportunities, risk flags, and wealth moves with estimated dollar impact per recommendation
Advisor conversion mechanism: Positioned the insights panel as the core business driver, translating client engagement into scheduled advisor actions
The Problem:
Consumers managing multiple LLCs, partnerships, and trusts had no way to understand how their entity structure fit together or how each entity affected their personal return.
The Solution:
Entity hierarchy visualization: Displays the full ownership structure, filing type, and status for each entity in a scannable org view and list view toggle
Immediate sophistication signal: Communicates OLarry's capability to high-value clients on first view, without requiring any explanation
The Problem:
The MVP had no mechanism to surface OLarry's core AI value. Insights existed in the system but had no place to live and no way to drive action.
The Solution:
Categorized insights feed: Organized by type, including savings, risk flags, wealth opportunities, and overspending, with estimated dollar impact on every card
Conversational AI threading: Each insight opens a direct AI conversation that explains the opportunity in plain language and provides actionable next steps
Intelligent escalation: Threads escalate to a human advisor when complexity warrants it, creating a natural handoff between AI and professional guidance
The consumer platform also includes Activities, Meetings, Documents, Filed Returns, My Tax Profile, and Settings; each designed with the same clarity-first principle.
The Problem:
No professional view: Tax advisors could only see a flat list of their clients, with no context, status, or filing information attached
No season-level awareness: There was no mechanism to surface where clients stood in the filing process or flag who was falling behind
No risk visibility: Advisors had no way to identify which clients were at risk across their entire portfolio at a glance
The Solution:
Client-centered dashboard architecture: Organized the dashboard around the four questions every client asks at the start of tax season, mapping each directly to a KPI card with year-over-year trend context
Prioritized action feed: Surfaced exactly what each client needs to act on next, with time estimates per task to reduce friction and set clear expectations
AI insights panel: Designed a dedicated panel that surfaces savings opportunities, risk flags, and wealth moves with estimated dollar impact per recommendation
Advisor conversion mechanism: Positioned the insights panel as the core business driver, translating client engagement into scheduled advisor actions
The Problem:
Tax professionals managing large client books had no way to understand what needed their attention across all clients simultaneously. Work was reactive — advisors had to manually check each client record to find blockers, unanswered messages, or stalled returns.
The Solution:
Prioritized action feed: shows the most urgent items across the entire client book: stale reviews, kicked-back returns, unanswered client questions. All ordered by urgency so advisors know exactly where to start
Split-panel detail view: selecting any action opens the full context on the right without leaving the screen, keeping advisors in flow rather than navigating between records
Client group activity inbox: with Urgency, Most recent, and Client sort options, grouping all messages, document events, and meetings per client group so nothing falls through the cracks
AI-surfaced signals: embedded directly in the feed, flagging when a return has been idle too long or a client question has gone unanswered, so advisors are proactive rather than reactive
The Problem:
Document intake was entirely manual. Advisors opened, read, and categorized every uploaded file before beginning a return, a significant source of time loss that scaled badly across a large client book.
The Solution:
Three-panel Gather workflow: Document request list on the left tracking received vs. missing, document viewer in the center, and AI-extracted field data with confidence scores on the right Verify, not transcribe: Advisors review and correct AI-extracted data rather than manually entering it, removing the most time-consuming part of document processing
Directly connected to Review: a worksheet-based reconciliation surface with projection vs. actual columns, per-schedule drill-down, and inline flags, the full picture from intake to sign-off in one continuous flow
Contextual AI bar: Allows advisors to ask questions about any document in the context of that client's full tax picture, surfacing relevance without switching screens
