Users who sold bitcoin needed tax documents. We'd never delivered them before.
This was the user-facing piece of Fold's first tax season: an in-app experience where users could confirm their info and download their 1099-B and Gain/Loss Summary.
What I Built
Proactive communication (shipped first) - Before the feature was built, I shipped emails to impacted users, a support article explaining what to expect, and an in-app "coming soon" banner. All targeted only at users who had sold bitcoin that year. This reduced support tickets dramatically while engineering was still building.
Pre-filled W-9 flow - Most TaxBit clients use TaxBit's SDK to collect user info at onboarding. We couldn't; Fold already had robust PII collection. Instead, I pre-filled the W-9 with data we already had (name, address, SSN). Users just confirmed. If they could sell bitcoin, they already had a debit card, which meant we had their info.
Document download page - Simple in-app page where users could download their 1099-B (PDF) and Gain/Loss Summary (CSV). Tappable components, clear labeling, no confusion.
Support article and FAQ - I wrote the documentation, gathered questions from Support as they came in, and worked with TaxBit to answer them. The article grew with the questions users were actually asking.
Key Product Decisions
Deliver both 1099-B and Gain/Loss Summary. The 1099-B serves most users; they just want a number to plug into TurboTax. But we also have hardcore Bitcoin enthusiasts who want to understand their transactions and potentially adjust their disposition method. The Gain/Loss Summary serves them. Low incremental lift (TaxBit already generated it), high impact for serving the full user spectrum.
Use FIFO disposition method for 1099-B. After researching competitors and talking to TaxBit and users, I chose FIFO (First In, First Out) as the default. It's what most users expect and what most platforms use. Power users who want different methods can use the Gain/Loss Summary.
Ship communication before building. Users were already getting tax emails from Coinbase and Robinhood. I could reduce anxiety immediately with zero engineering effort. High impact, low lift.
Impact
- ~50 support tickets across ~5,000 eligible users (1% rate); only ~10 were actual issues
- Met mid-February compliance deadline with a month to spare
- 80% of users downloaded only the PDF; 20% downloaded both formats
- Proactive communication reduced "where are my tax docs?" tickets to near-zero before launch
Skills
Compliance coordination, proactive communication, user segmentation, cross-functional execution