Phase 01 - Diagnosis
FSA and HSA accounts are genuinely valuable - but only if users can understand them. The existing platform assumed a level of benefits literacy that most users simply didn't have, and the interface did nothing to close that gap.
The product covered the full lifecycle of consumer health benefit accounts: checking balances across FSA and HSA accounts, reviewing eligible transactions, submitting reimbursement claims, and completing the CIP (Customer Identification Program) process to open an HSA. On paper, it was comprehensive. In practice, users were left to decode complex financial terminology, unclear account hierarchies, and dense transaction views with no guidance on what they were looking at or what to do next.
The original interface had no design system, no consistent component patterns, and no governing hierarchy for how information was weighted. Each screen felt like a separate design decision - which meant users who moved between them lost their bearings constantly. The product had accumulated features without ever establishing the visual and structural language needed to hold them together coherently.
The users weren't confused because benefits are complicated. They were confused because the interface never helped them build a mental model of their own money.
Phase 02 - Research in the wild
Understanding how general public users interact with financial health products required getting out of the building. I used guerrilla testing - real people, real reactions, no lab - followed by structured moderated sessions to go deeper on what the street testing revealed.
Guerrilla testing was the right entry point here precisely because FSA and HSA literacy varies enormously in the general public. Some users had never heard of an FSA. Others had accounts they'd never fully used. Taking the existing product to public spaces gave me fast, unvarnished signal: where did people's understanding break down, what terminology stopped them cold, and which flows felt logical versus arbitrary.
The patterns were striking and consistent. Users could not reliably distinguish between their FSA and HSA accounts on screen. The reimbursement submission flow was abandoned at high rates - not because users didn't want to claim, but because they couldn't tell if they were doing it correctly. The CIP process for opening an HSA felt like an interrogation with no explanation of why each piece of information was needed or what would happen next.
Moderated sessions followed with users who had active benefit accounts. These sessions were task-based - submit a reimbursement, find your balance, understand an eligible transaction. Watching users navigate the existing product while thinking aloud produced a precise map of the decision points where confidence broke down. This fed directly into the affinity mapping phase.
Phase 03 - Synthesis and system design
The affinity maps grouped observations by behaviour pattern - not by feature. This reframing was critical: it prevented the redesign from inheriting the old product's structure and revealed the four failure modes that cut across every part of the experience.
The four patterns were: inability to establish account context (users couldn't quickly orient to which account they were in and what its current state was), terminology breakdown (benefit-specific language used without definition or scaffolding), action uncertainty (users couldn't confidently identify what to do next after any given state), and process opacity (multi-step flows like CIP felt like black boxes with no progress model).
Before a single redesign screen was produced, I established the design system: component patterns, typographic hierarchy, spacing rules, and a consistent interaction model for status, action, and confirmation states. The system was the precondition - not a deliverable to follow the redesign. Every screen that followed was an expression of the same rules, not a local creative decision made in isolation.
Alegeus operates as a white-label platform - the product is adopted by benefit providers (employers and their administrators) who brand and configure it for their own end users. This meant the redesign couldn't assume a fixed visual identity. To solve for this, I designed a CMS configuration page for admins - the benefit provider layer - that allowed them to apply their own theming: brand colours, typography, logo, and tone. The design system's token architecture made this possible cleanly: admins could remap the surface without breaking the underlying component structure or interaction logic. Any client could make the platform feel like their own product without redesigning it.
The redesigned flows addressed each failure mode directly. Account context was established at every entry point - balance, account type, and status were always visible and always scannable. Benefit terminology was progressively explained inline rather than assumed. Reimbursement flows were rebuilt with clear progress indicators, explicit eligibility signals, and confirmation states that told users their action had registered. The CIP process was redesigned as a guided, human-toned experience - each step explained, each data request justified, and progress always visible.
Phase 04 - Benefits Whisperer (hackathon)
At a hackathon, I reimagined the entire platform around a different premise: what if your benefits account had a team of specialists working behind the scenes - each one an expert in a specific domain - and the interface was simply where they surfaced their insight to you?
The concept was called Benefits Whisperer. Rather than a dashboard you navigate, it was a proactive, personalised experience driven by a multi-agent AI architecture. Each agent had a named role and a specific domain of expertise - together they formed an internal advisory system that monitored your accounts, transactions, and health profile, and surfaced exactly the right guidance at the right moment.
The agent system was orchestrated in two tiers. At the top, Orion acted as the orchestrator - receiving event triggers and user chat input and routing to the right specialist agents. Sherpa functioned as the planner, coordinating multi-step reasoning across agents before surfacing a response. Below them, a layer of specialist agents handled distinct domains: Bella (Benefit Sage) for plan guidance and eligibility, Cory (HSA Contribution Coach) for optimising tax-advantaged contributions, Ivy (Investments Guru) for HSA investment decisions, Una (Utilisation Guide) for spending and reimbursement coaching, PepTalk for behavioural nudges and engagement, PayMint for payment actions, and Pulse for health and benefit trend monitoring. External vendor agents - MolarMole (dental coverage) and DontGoBrokeR (telehealth scheduler) - connected the system to third-party services via an MCP server layer.
The UI reflected this architecture directly. Rather than a menu of features, the home screen was a Personal Health Benefit Assistant - a living, personalised surface showing proactive insights and recommendations generated by the agent layer based on the user's past interactions, transaction history, and benefit utilisation patterns. A health recommendations screen surfaced agent-generated, contextually relevant suggestions (not generic tips). An HSA contribution analysis screen combined Cory and Ivy's outputs into a rich investment opportunity view. A separate HSA Investment Opportunity view brought financial projection intelligence directly into the platform.
The design challenge was not building the agents - it was designing the interface layer that made a complex multi-agent system feel like one calm, trustworthy advisor. Every surface had to feel coherent and purposeful, not like a chatbot with extra features bolted on.