Product Design
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.
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Daryle M. // UI Designer
Nikolas P. // UI Designer
Sahil B. // UI Designer
Teresa S. // UI Designer
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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.
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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.
