Megan Casebier
About

Design leadership for complex, high‑stakes systems

Sole product designer at Obie, a fintech platform acquired for $500M. I build 0→1 B2B products in regulated industries, align cross‑functional teams under pressure, and ship on deadlines that actually matter.

I design the systems behind the screens.

I’m a product designer who thrives on the hard stuff — building 0→1 products in regulated industries, working inside technical constraints that make most designers uncomfortable, and shipping under real deadlines with real stakes. I spent the last few years as the sole product designer at Obie, a fintech platform acquired for $500M, where I designed production systems serving 1,300+ insurance agencies.

My best work happens before Figma is open: running customer research, mapping data flows with engineering, and framing the tradeoffs that determine whether a product ships on time or doesn’t ship at all. I also run usability validation and track outcomes after launch to confirm the system is working, not just beautiful. I’m looking for a team that’s building something ambitious and needs a designer who can lead from day one.

Leadership

I align engineering, product, underwriting, and operations by making tradeoffs explicit and decisions legible. I’m comfortable leading in ambiguity and moving quickly without sacrificing quality.

Systems Thinking

I question the data model, not just the UI. If the system is wrong, the interface will always be wrong. That’s why I get close to architecture and constraints early.

AI‑Accelerated

I use AI prototyping to compress feedback cycles from weeks to days. Working prototypes drive better stakeholder alignment than static mockups.

Customer‑Driven

I rely on direct customer research, usability testing, and operational workflows — especially in regulated products where edge cases drive the system.