Obie 2.0: Building Trust Through Design

Obie is rethinking landlord insurance—making it faster, simpler, and broker-free for real estate investors. But our old brand didn’t reflect that. After bringing in an external agency to lead the rebrand, the team quickly lost confidence in the direction. The proposed designs were too safe, too generic, and didn’t feel connected to the product or our customers. So we pivoted. Fast. Rather than start another agency search, I led the internal effort to define a new brand direction that felt true to who we already were—and who we were becoming.

❗️The Challenge

This wasn’t just about updating visuals. We had to:

  • Win back internal trust after a failed rebrand attempt

  • Create a brand identity that felt clear, modern, and trustworthy

  • Bridge marketing, product, and CX into one cohesive system

  • Move quickly without sacrificing quality

Obie 2.0: Building Trust Through Design

Obie is rethinking landlord insurance—making it faster, simpler, and broker-free for real estate investors. But our old brand didn’t reflect that. After bringing in an external agency to lead the rebrand, the team quickly lost confidence in the direction. The proposed designs were too safe, too generic, and didn’t feel connected to the product or our customers. So we pivoted. Fast. Rather than start another agency search, I led the internal effort to define a new brand direction that felt true to who we already were—and who we were becoming.

❗️The Challenge

This wasn’t just about updating visuals. We had to:

  • Win back internal trust after a failed rebrand attempt

  • Create a brand identity that felt clear, modern, and trustworthy

  • Bridge marketing, product, and CX into one cohesive system

  • Move quickly without sacrificing quality

Our Approach

We stripped it back to the fundamentals:

  • Aligned on core brand principles: clarity, confidence, calm

  • Audited competitors to understand tone and visual whitespace

  • Rebuilt the identity in-house, starting with real product context, not theoretical mockups

  • Worked with an external illustrator to create a flexible visual system grounded in our user journey

  • Tested the identity as we built it—across our quote flow, marketing site, and outbound materials

Final Brand Direction

We delivered a fresh identity rooted in product clarity and emotional trust:

  • Refined logo — Slightly tweaked for better legibility and balance at small sizes

  • Color palette — A rich, dark green base for stability, paired with a vibrant chartreuse accent for energy and clarity

  • Typography — A modern serif + geometric sans pairing that brought warmth to headlines and structure to the UI

  • Custom illustrations — Created in partnership with an external designer to represent Obie’s product benefits in a clean, human way

  • Real UI moments — Product screenshots and flows featured front and center across pages to build immediate understanding and trust

This was more than a visual facelift—it was a realignment of how Obie feels and communicates across every touchpoint.

Positioning Through Design

As we moved away from the agency’s work, it became clear the brand needed to do more than just look good — it needed to communicate Obie’s ambition to be the most trusted, user-first insurtech provider in the market.

Rather than chasing trends, I leaned into a design language that reflected clarity, confidence, and product maturity — values that aligned with where Obie was headed, not just where we were.

From colors to type, from layout to illustration, every decision was made to elevate Obie’s position in a crowded industry, while making sure we stayed approachable, fast-moving, and trustworthy.

Results & Impact

  • 💬 Immediate buy-in from stakeholders who had been frustrated with the agency process

  • 🎨 Brand applied consistently across product, marketing site, and outbound collateral

  • 🔄 Faster collaboration between product, CX, and marketing teams

  • 🖥 Improved engagement on early marketing pages using the new brand system

  • 🧱 A scalable foundation ready for new features, new messaging, and future growth

My Learnings

  • The best rebrand direction often comes from within.
    After the agency fell short, our internal alignment and product context gave us the clarity the brand needed.

  • You don’t need multiple prototypes to know what feels right.
    The direction we chose came together naturally once we focused on real use cases, not moodboards.

  • Clarity is the most powerful differentiator.
    Every decision—from color to typography to copy—was rooted in building user confidence in high-stakes flows.

  • Cross-functional buy-in is easier when the work feels familiar.
    By designing with live product flows and collaborating across teams, we earned trust early and often.

  • Visual polish matters most when the product is already strong.
    The rebrand didn’t invent a new story—it simply helped Obie show up the way it already worked.

View our Brand Book

Click above to see our full rebrand!

Black and white portrait of a man with a beard and glasses

Pablo Barrera

Lead/Senior Product Designer

Contact

Fill out the form, or reach out directly. I’ll respond within 24 hours.

© Copyright 2026. All rights Reserved.

Design by

Pablo Barrera

Black and white portrait of a man with a beard and glasses

Pablo Barrera

Lead/Senior Product Designer

Contact

Fill out the form, or reach out directly. I’ll respond within 24 hours.

© Copyright 2026. All rights Reserved.

Design by

Pablo Barrera

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