01
The tax filer
Brings life context, priorities, and final submission authority.
TurboTax Expert Assist
Overview
Pioneering the benchmark AI + HI (Human Intelligence) collaboration paradigm in consumer fintech—orchestrating proactive AI intelligence and certified tax professionals into a seamless, trust-anchored co-filing experience.
My Role
Design LeadPlayer-Coach
Category
AI + Human Intelligence (AI+HI)•Design strategy•Cross-platform
Stakeholders
Product ManagementContent DesignMarketingCustomer Success
Objective
Tax filing is universally recognized as a high-stress, high-anxiety financial milestone. While self-filers appreciate the affordability of DIY software, they often hit a "confidence wall" when navigating complex tax codes, 1099 investments, or business deductions. Pure automation lacks the emotional reassurance filers need, while pure human services don't scale.
TurboTax Expert Assist bridges this gap as an industry-defining AI + HI (Human Intelligence) product. It pairs continuous, proactive AI intelligence with on-demand access to certified tax experts (CPAs and Enrolled Agents)—culminating in an algorithmically optimized, human-verified 100% accurate return.
The Core Challenge
How do we orchestrate a collaborative triad between the filer, AI, and tax professionals by harnessing deduction discovery and speed without compromising human agency, empathy, and accountability?
One filing experience
The AI + HI Collaboration Triad
Three distinct strengths, deliberately orchestrated around a single, confident decision.
Life context, priorities, and final authority.
Signals, document intelligence, and deduction discovery.
Judgment, reassurance, and a human-verified return.
My Role
On this project, I stepped into a hybrid player-coach leadership role. While I was hands-on in the trenches designing the high-stakes end-to-end flows, I also operated as the de-facto design manager for our product vertical—handling all aspects of design leadership and project management.
Team
3 Product designers, 1 Content Designer, 1 UX researcher
Cross-functional Stakeholders
4 Product managers, Engineering, Marketing, Tax Experts, Legal, and Customer Success teams.
Problem Space
For tax year 2025, I worked with product managers and the researcher to conduct baseline qualitative interviews with DIY filers, analyzed customer support logs, and reviewed drop-off telemetry from the previous tax season. We mapped findings across three core user mindsets:
Onboarding & Value
The "Am I in the Right Place?" Anxiety
Customers felt overwhelmed immediately after signing up. They didn't understand what "Expert Assist" actually meant or how they would be paired with an expert.
The Blind Leap
Users were hesitant to pay or commit without understanding if a real tax professional could truly solve their niche tax scenarios (e.g., self-employed write-offs).
The Filing Journey
Context Loss & Repetition
Users hated having to explain their situation over and over again if they got disconnected or returned to the app days later. They wanted a continuous relationship.
Reactive Paralysis
Many users got stuck on complex forms but hesitated to hit "Get Help" because they couldn't clearly articulate what they were confused about. They needed a way to bookmark issues as they went.
Validation & Wrap-Up
The Fear of the "Submit" Button
Even after getting help, the final step of filing caused a spike in anxiety. Users wanted confirmation that their deductions were fully maximized and legally bulletproof.
Expert Inefficiencies
Internal data showed that experts struggled to guide users through the final review because their internal tooling lacked clear visual markers of what the customer was looking at on their screen.
Design Strategy
1
Start with confidence
Demystify the expert offering immediately. Use matching to instantly connect users to specialized experts and lead with concrete value (such as reviewing prior-year tax returns).
2
Partner Throughout
Foster a continuous human connection. Design features that allow users to reconnect with their previous expert, use proactive triggers to help stuck users, and implement "Tax Bookmarks" so users can collect questions and sync up asynchronously.
3
End with Assurance
Deliver absolute peace of mind. Combine the precision of AI-driven Deductions & Credits agents with expert validation, backed by an overhauled expert portal that enables seamless, real-time guidance.
What I worked on
Here is a select list of projects I worked on. Note that this is not an exhaustive list.
Expert matching
Description
A smart routing engine that instantly matches the user with a targeted expert (e.g., Schedule C specialist) right after authentication.
Impact
Helped create a standardized matching experience across all Turbotax Assisted products, with 8% increase in the key metric start-to-complete.
Proactive intervention
Description
Contextual, smart UI triggers that offer expert help when a user hesitates or exhibits "looping behavior" on complex tax forms.
Impact
Improved assisted-session attachment (users who start an expert interaction) by 12%, driving higher completion and fewer drop-offs.
...and more
| Project | Details | Impact |
|---|---|---|
| Prior-Year Return Optimizer | A micro-flow during onboarding offering to have an expert review the user's previous tax return to find missed deductions. | Increased early-session confidence and improved Expert Assist attachment by encouraging customers to start with a high-value review. |
| Streamlined Onboarding | A redesigned onboarding wizard that clearly explains how and when to contact an expert without delaying their progress. | Reduced onboarding confusion and drop-off; improved time-to-first-action by making “what happens next” and support options explicit. |
| Expert Reconnection | A persistent "My Expert" profile card allowing returning users to reconnect with the exact same expert they spoke to previously. | Improved continuity across sessions and repeat usage; reduced re-explaining effort for customers and ramp time for experts. |
| Bookmarks | An interactive bookmarking experience allowing users to tag any section, write down questions, and batch them for their next expert session. | Lowered friction to asking for help and reduced context loss; enabled faster, higher-quality expert sessions by bundling questions with location/context. |
| AI + Human D&C Agent | An AI agent that highlights potential missed deductions & credits, which the expert then verifies live with the customer. | Increased perceived value and trust at final review; improved deduction/credit discovery rate while keeping expert validation as the safety net. |
Prior-Year Return Optimizer
Details
A micro-flow during onboarding offering to have an expert review the user's previous tax return to find missed deductions.
Impact
Increased early-session confidence and improved Expert Assist attachment by encouraging customers to start with a high-value review.
Streamlined Onboarding
Details
A redesigned onboarding wizard that clearly explains how and when to contact an expert without delaying their progress.
Impact
Reduced onboarding confusion and drop-off; improved time-to-first-action by making “what happens next” and support options explicit.
Expert Reconnection
Details
A persistent "My Expert" profile card allowing returning users to reconnect with the exact same expert they spoke to previously.
Impact
Improved continuity across sessions and repeat usage; reduced re-explaining effort for customers and ramp time for experts.
Bookmarks
Details
An interactive bookmarking experience allowing users to tag any section, write down questions, and batch them for their next expert session.
Impact
Lowered friction to asking for help and reduced context loss; enabled faster, higher-quality expert sessions by bundling questions with location/context.
AI + Human D&C Agent
Details
An AI agent that highlights potential missed deductions & credits, which the expert then verifies live with the customer.
Impact
Increased perceived value and trust at final review; improved deduction/credit discovery rate while keeping expert validation as the safety net.
Customer Quotes
“Before I talk to a tax expert, I would go back to these bookmarks. Between that and my notes, I'm ready for a telephone conference now.”
R
Randy
about Bookmarks“I was very surprised and happy to see [PYRO offer]...it’s just not something you’d expect - seeing a company go the extra mile. It surprised me to see TurboTax take that extra step to show that you’re not missing out on something.”
B
Bruce
about PYRO“Fortunately, I signed up for live agent...that’s been very good. I really like the ability, once I get a person, that I could actually schedule another call with that person who’s already familiar with some of my questions. Fabulous.”
T
Tom
about ReconnectingTT
Impact
3y%
increase in users completing their taxes YoY
3y%
increase in revenue YoY