Outdoorsy 1099-K Issuance

In October 2021, Outdoorsy had a compliance liability: the company needed to provide 1099-K forms to RV hosts who had reached IRS income thresholds.

Working within a three-month timeline, our design solution successfully met two important milestones for the company and hosts on the platform:

  1. W-9 collection by end-of-tax-year — We needed complete W-9 data before annual transaction totals were finalized. If a host crossed the threshold on December 31, we needed their tax info already on file.

  2. 1099-K filing by January 31 — Once we knew who qualified and had their information, we had one month to generate, file with the IRS, and deliver forms to hosts.

Complete case study coming soon...

    • Daryle M. // Lead Designer

    • Ilario H. // Product Manager

    • Sarah W. // Senior Content Designer

  • Close collaboration on owner information collection and completed form issuance flows, along with compliance deadline messaging.

  • The resulting experience affected every active host on the platform, leading to collecting W-9 tax information from ~20,000 hosts and full compliance for four consecutive tax years.

  • "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

  • "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

  • "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

  • "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

  • "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