Scott Aquilino
Duration: 4 Sprints
Context and Problem
Ahead of Medicare open enrollment, we saw an opportunity to provide guidance to our target audience, helping them navigate a complex decision while creating a natural path into Considerable.com. I led product design, driving a rapid, cross-functional effort to launch a Medicare decision tool that could capture and convert this audience.
Key Questions & Core Problems
- How might we enter the Medicare space quickly without compromising credibility or clarity for a 50+ audience?
- How do we balance speed-to-market with the need for accurate, trustworthy guidance in a complex domain?
- What is the simplest way to guide users through a high-stakes decision (Supplement vs. Advantage)?
- How do we align product, content, and marketing around a single, focused experience?
Opportunity
- Turn Medicare guidance into an interactive experience that engages users, guides decisions, and increases daily active users to support ad revenue growth.
Process
Content-Led Prototyping
Positioned content as the primary driver of the experience to ensure clarity and trust. We passed google slides back and forth with the subject matter expert to get quick feedback on the content and logic.
- Used simple tools to rapidly iterate on question flow and decision logic
- Partnered closely with subject matter expert to validate accuracy and tone
- Ensured questions mapped directly to meaningful user outcomes
Rapid Concept Alignment
Established a lightweight, decision-focused workflow to replace traditional design cycles and meet the deadline.
- Prioritized speed by eliminating wireframing in favor of low-fidelity concepting
- Facilitated tight product loops with PM, engineering, and subject matter expert
- Aligned early on core experience: a guided decision tool rather than static content
Cross-Functional Validation
Scaled feedback quickly across the organization to reduce risk pre-launch.
- Leveraged informal QA and stakeholder reviews to validate usability and clarity
- Incorporated feedback loops into daily workflow to maintain velocity
- Built shared understanding across teams without formal handoff processes
Experience Differentiation
Introduced lightweight interaction patterns to increase engagement without slowing delivery.
- Focused on moments of feedback and progression to reinforce user confidence
- Balanced simplicity with delight to improve completion rates
- Ensured design decisions supported both product and marketing goals
Results
Impact & Strategic Alignment
Delivered Considerable’s first Medicare-focused product, establishing a foundation for growth in a key revenue category.
- Enabled entry into the Medicare market ahead of open enrollment
- Aligned product, content, and marketing around a single acquisition experience
- Demonstrated a repeatable model for rapid, cross-functional product delivery
Measured Outcomes
The quiz drove meaningful engagement and validated the viability of interactive tools for conversion.
- Increased user engagement through a guided, high-completion experience
- Created a new top-of-funnel entry point tied to Medicare-related revenue
- Accelerated time-to-market, allowing the business to capitalize on a time-sensitive opportunity