Watchtower Benefits

Watchtower Benefits was an early-stage InsurTech startup working with DESIGNATION (now the Flatiron School) as part of the school's embedded startup partnership program.

WatchTower Benefits was building SaaS technology to modernize the Request for Proposal process in the non-medical employee benefits space — using proprietary document extraction to bring accuracy and transparency to a process that had long relied on manual, email-based workflows between insurance brokers and carriers. My team was brought in on a focused UI engagement: executing service design and high-fidelity interface work for their beta platform. Watchtower has since rebranded as ThreeFlow, raised $87.8M in venture funding from investors including Accel and Emergence Capital, and manages $3.7B in annual premium.

The complete UX process documentation for this project lives at the direct link below.

Read the complete case study

    • Daryle M. // UI Designer

    • Nikolas P. // UI Designer

    • Sahil B. // UI Designer

    • Teresa S. // UI Designer

  • Conducted competitive analysis of the insurance broker and benefits technology landscape to establish UI benchmarks and identify visual differentiation opportunities. Designed high-fidelity interface screens for Watchtower's beta platform within a four-person UI team, translating complex insurance workflow requirements into a clear, professional SaaS interface. Focused on information hierarchy and visual clarity — critical in a space where users are navigating dense policy data and multi-party collaboration workflows.

  • Delivered best-in-class UI design for Watchtower's beta platform at a pivotal moment in the company's development. The engagement provided production-ready interface work that supported the company's early product evolution. Watchtower subsequently rebranded as ThreeFlow, secured $87.8M in total funding, and has grown into the leading benefits placement system in the US insurance market — managing $3.7B in annual premium and serving brokers and carriers across the country. The work here represents an early contribution to a product trajectory that validated the market problem from the ground up.

  • 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

  • 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

  • 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 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