Megan Casebier · Product Designer

I turn impossible constraints into elegant, simple systems

Sole product designer on a fintech platform acquired for $500M. I’ve built 0→1 B2B products from blank canvas to production, designed systems for 1,300+ agency partners, and shipped new business lines under hard deadlines — while running customer research, testing workflows, and measuring outcomes in regulated environments.

Currently Open to founding & lead design roles
Previously Obie (acquired for $500M), StrongArm Tech
Focus 0→1 B2B products, complex systems, regulated industries
Selected Work
Obie Homeowners Insurance quoting system
Obie · Post-Acquisition · 0→1
Designing a new line of business in four months after a $500M acquisition
I led the design of Obie's first homeowners insurance product — a completely new quoting system built from scratch on a platform that was never designed for it, shipped on a hard April deadline with measured readiness and rollout controls.
In progress
Obie · Emergency Redesign · 2.5 Weeks
Rebuilding partner authorization under deadline pressure
When the launch risked failing, I reframed the data model, led a 2.5‑week redesign, cut database complexity by 99.7%, and validated workflows with stakeholders before release.
Coming soon
Case Study
Enterprise design system
Scaling design decisions across a multi-product platform. Full case study in progress.
Coming soon
Case Study
Workflow automation
Reducing manual processes for operations teams in regulated environments. Full case study in progress.

“Megan is the rare designer who operates comfortably inside complex systems. She consistently translated ambiguity, constraints, and conflicting inputs into clear, decision-ready insight for product and engineering leadership.”

Valeska O’Leary — Executive Director of Design, StrongArm Tech
Megan Casebier
About

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’m looking for a team that’s building something ambitious and needs a designer who can lead from day one.

More about me →