Megan Casebier · Product Design · Systems & Platforms

One UX designer. Four product teams. A platform that grew revenue over 2,100% and was acquired by The Baldwin Group (NASDAQ: BWIN).

I’m the sole UX designer at Obie — an insurtech platform acquired by The Baldwin Group (NASDAQ: BWIN). I lead all UX strategy across 4 PMs and 4 TPMs, coach a UI designer, and own the information architecture, research, and product design for a platform serving a nationwide agency partner network. No design manager. Just hard problems in regulated environments, solved with systems thinking and shipped under real deadlines.

Previously Obie (acquired by The Baldwin Group), StrongArm Tech
Focus 0→1 B2B products, complex systems, regulated industries
Selected Work
Design QA walkthrough tool showing severity coding, issue tracking, and design-vs-implementation comparisons
Obie · Design QA · AI-Assisted Development
Building a tool that shipped 52 design fixes without consuming a single sprint point
Instead of filing 52 Jira tickets, I built an interactive QA walkthrough that combined human design review with AI-powered analysis. One front-end engineer resolved every issue between planned tickets in a single sprint — zero disruption to the roadmap.
Obie Homeowners Insurance quoting system
Obie · Post-Acquisition · 0→1
Designing a new line of business in four months after the 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.

“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 platform, not the feature.

For the past four years I’ve been the sole UX designer at Obie — an insurtech platform acquired by The Baldwin Group (NASDAQ: BWIN). No design manager above me. I lead all UX strategy across four product teams, coach a UI designer, and own the information architecture, research, and design systems. The platform I design for serves a nationwide agency partner network across multiple product lines in a regulated industry where a wrong state can trigger a compliance incident.

My best work happens before Figma is open: mapping data models with engineering, diagramming state machines, and framing the tradeoffs that determine whether a product ships on time or doesn’t ship at all. I’m looking for a team building complex systems that needs a designer who operates at the platform level.

More about me →