Product Design
Outdoorsy 1099-K Issuance
In late 2021, new IRS reporting requirements created an immediate compliance liability for Outdoorsy.
The company needed to collect W-9 tax data from qualifying RV hosts and issue 1099-K forms — on a compressed government-mandated timeline.
The design challenge wasn't just technical. It was communicating complex, high-stakes tax obligations clearly to platform users who were RV owners, not accountants, in a way that drove action without creating alarm.
Collecting complete W-9 data for RV hosts before their rental income totals were finalized. If a host crossed the income threshold on December 31, Outdoorsy needed their tax info already on file.
Once qualifying hosts were identified, Outdoorsy had one month to generate 1099-K forms, file with the IRS, and deliver to hosts.
-
Outdoorsy faced a hard deadline with two sequential milestones: collect complete W-9 data from RV hosts before their rental income totals were finalized, then generate and deliver 1099-K forms within one month of the tax year closing. Missing either milestone meant IRS non-compliance. The UX challenge: design flows that made unfamiliar, anxiety-inducing tax processes feel clear, manageable, and trustworthy — at scale, across a diverse host population.
-
Ilario H. // Product Manager
Garrett M. // Senior Front-End Developer
Daryle M. // Lead Product Designer
Sarah W. // Senior Content Designer
-
Led product design across two distinct flows: a W-9 data collection experience for RV hosts and a 1099-K form issuance experience. Worked in close collaboration with product management, front-end engineering, and content design to ensure clarity of language, urgency of deadline messaging, and accessibility of the tax concepts for a non-expert audience. Designed within Outdoorsy's existing design system while meeting strict compliance requirements for both flows.
-
The solution successfully met both IRS compliance milestones. The W-9 collection flow captured tax information from approximately 20,000 active hosts before year-end income thresholds were finalized. The resulting 1099-K issuance experience delivered compliant forms on time — and continued to serve the platform for four consecutive tax years, making it one of the most durable and high-impact design deliverables of the Outdoorsy engagement.
