Case Study: SimplyInsured achieves 100% online, HIPAA‑compliant insurance enrollment and mobile ID delivery in days with Dropbox Sign

SimplyInsured Uses eSignatures to Redefine an Industry

SimplyInsured, a San Francisco–based platform that helps small businesses buy and manage health insurance, faced a major hurdle: typical enrollments required 5–20 signatures across multiple documents, making a fully digital, mobile-first experience difficult. Building an in‑house eSignature system would have taken months, so the team evaluated providers and selected HelloSign for its clean API and reliability to make eSignature a core piece of infrastructure.

Using HelloSign’s API, SimplyInsured completed integration in four days and transformed enrollment into a 100% online, 10‑minute process that delivers mobile insurance ID cards in days and meets HIPAA standards. The change enabled thousands of processed applications, helped insure 6,000 customers, saved small businesses roughly $500–$1,000 per employee per year (about $25M total to date), and improved customer satisfaction with highly responsive support.

SimplyInsured

Vivek Shah

Co-Founder and CEO