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.

  1. 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.

  2. Once qualifying hosts were identified, Outdoorsy had one month to generate 1099-K forms, file with the IRS, and deliver to hosts.

Detailed case study coming soon

Outdoorsy host account - tax documents view

  • Outdoorsy faced a hard deadline with two sequential milestones: collect complete W-9 data from RV hosts before 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: make 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: W-9 data collection for RV hosts and 1099-K form issuance. Worked closely with product management, engineering, and content design to ensure clarity of language, urgency of deadline messaging, and accessibility of tax concepts for a non-expert audience.

    Designed within Outdoorsy's existing design system while meeting strict compliance requirements for both flows.

  • The solution 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 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 deliverables of the Outdoorsy engagement.

  • Thinks about the entire 360 of his work

    "Daryle is a superb human being, kind, funny and caring. He brings those qualities, plus his incredible design skills, to his work day in and day out. Daryle thinks about the entire 360 of his work, from the impact his designs have on engineering to how the end user will experience them. He took the lead on accessibility for our team, continually sharing valuable guidance with designers and others in a way that was easy to understand and act on. On top of all that, he always has a smile and a music recommendation (probably someone you’ve never even heard of) at the ready."

    — Sara Womack, UX Writer & Content Strategist

  • An obvious passion for the user-centered design process

    "Daryle is an exceptional UX professional with a keen eye for detail and an obvious passion for the user-centered design process. He has demonstrated a consistent ability to influence product strategy by leveraging data and insights, along with a natural ability to clearly articulate the rationale behind his decision-making. I have no doubt that Daryle's experience will help elevate any design/product team and I am thankful for the opportunity to have worked with him."

    — Dion Alexander, Product Design Consultant

  • The ability to translate complex problems into ultra-intuitive, elegant solutions

    "One of Daryle’s standout strengths is his ability to simplify complex problems and translate them into ultra-intuitive, elegant solutions. He demonstrated this by taking a predominantly paperwork, owner-to-renter process and transformed it into a mobile-first experience. He also brings a deep understanding of accessible design and was instrumental in guiding both our design and engineering teams toward building inclusive components that serve a broad range of users."

    — Ben Richard, Product Design Leader

  • The first designer I've worked with who was interested in the data behind the designs

    "Daryle is a very skilled designer who devotes a lot of time working with engineers and other designers to build sophisticated UI. He was involved with several projects I worked on, and I couldn't get over just how many designs he created that covered every aspect of the feature. His designs are clean and very pleasing to the eye. I appreciated that he was always available to answer questions whenever needed. He was also the first designer I've worked with who was interested in the data behind the designs. Highly recommended!"

    — Marty Miller, Senior Android Developer

  • Valiantly represents the customer throughout the product experience

    "I had the pleasure of working with someone that was both a brilliant designer and friend. Daryle and I collaborated for over a year across various projects and building out our design system. Daryle is incredible at providing thoughtful feedback, and I was most stricken by how valiantly he could represent the customer throughout the product experience. His positive attitude will be missed, but I look forward to following his impeccable DJ holiday sets. I highly recommend Daryle if you need a great design lead!"

    — Chije Wangati, Senior Product Designer