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Web Design
Web Development
Graphic Design
Insurtech

StretchDollar: Simplifying Small Business Benefits

StretchDollar is the accessible benefits platform for growing teams, bridging the gap between complex insurance mandates and the flexible, personalized coverage small businesses need.

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Friction

Trust Gap

StretchDollar had a powerful mission—simplifying insurance for SMBs—but their digital presence was idling. The original website lacked the visual authority to compete in the high-stakes insurance market.

This "optical immaturity" created friction for risk-averse business owners who hesitated to trust a financial partner that didn't look the part.

Calibration

Trust Through Utility

We engineered a translation layer. The strategy focused on stripping away insurance jargon and replacing it with clear, human-centric design. We transformed the website from a static brochure into a dynamic resource, using front-facing tools to prove to business owners that "simple insurance" was a reality, not just a tagline.

Build

The Marketing Engine

We executed a complete overhaul of the public-facing web experience to drive education and conversion:

  • Interactive Utility: Engineered custom web-based calculators that allow users to simulate savings and budgets instantly, without requiring a login.
  • Content Velocity: Identified high-performing pages (such as state guides) and rebuilt them as flexible CMS collections, empowering the team to scale SEO instantly without developer reliance.
  • Visual Governance: Developed a cohesive graphic library and typography system that balances approachability with financial credibility.
Velocity

Capital Validation

The elevated web experience validated the brand's maturity to both customers and capital partners. After professionalizing the digital "front door," StretchDollar secured a $6M Seed round in 2024, proving that a friendly, accessible brand can still command serious market authority.