SimplyInsured

SimplyInsured was founded with one mission: to eliminate fear from health insurance. By changing the way small business owners purchase health insurance with our 100% online platform, we’re transforming a $20 billion dollar industry and delighting thousands of customers.

Our unique values-based culture (and extremely talented team) is our core competitive advantage, and each person on our team makes a direct, immediate impact on our business.

We value transparency, feedback, bias to action, growth, and an obligation to dissent. Every opinion is respected, we hold each other to extremely high standards, we’re driven by the diversity in our backgrounds, and unified by 100% alignment on our mission.

What’s best for the customer is the heart of everything we do, and our customer stories prove it: by changing health insurance we’re literally saving lives.

Based in San Francisco, SimplyInsured was founded in 2012 and is back by Bessemer Venture Partners, Polaris Ventures, and Y-Combinator. If you’re up for the challenge of improving health insurance for millions of Americans, we’re just getting started, and we’re growing!

High-Level Overview

SimplyInsured is a health insurance technology company that offers a 100% online platform for small businesses to compare, purchase, and manage health insurance plans, including medical, dental, and vision coverage. Their product serves small business owners who traditionally face complexity and fear in navigating health insurance options. By automating payroll deductions and providing unbiased plan recommendations, SimplyInsured simplifies the insurance buying process, saving customers money and time while improving access to quality coverage. The company has demonstrated strong growth, serving over 25,000 customers and saving them collectively over $50 million, supported by a team of around 90 employees and backing from top-tier investors like Bessemer Venture Partners and Y Combinator[1][2][3][5].

Origin Story

Founded in 2012 by Vivek Shah in San Francisco, SimplyInsured emerged from a mission to eliminate fear from purchasing and navigating health insurance for small businesses. Shah’s vision was to transform a traditionally opaque and cumbersome $20 billion industry by leveraging technology to provide transparency, ease, and customer-centric service. Early traction came from building a fully online platform that allowed small businesses to instantly compare hundreds of plans from all major carriers and apply online, a significant innovation compared to traditional brokers. The company’s culture emphasizes transparency, feedback, and high standards, which has helped it scale and continuously improve its offering[2][3][4].

Core Differentiators

• Product Differentiators: SimplyInsured offers access to thousands of plans from all major carriers nationwide, enabling small businesses to see and compare all available options in one place.
• Developer Experience: The platform is fully online with a streamlined application process that takes under 10 minutes, plus automated handling of paperwork and submissions.
• Speed, Pricing, Ease of Use: Instant quotes, 1-click payroll integrations with major platforms (e.g., QuickBooks, Square Payroll), and fully automated payroll deductions simplify administration and reduce errors.
• Customer Support: A dedicated team of licensed insurance agents provides ongoing support, including claims assistance, which is rare compared to traditional brokers.
• No Fees: The service is free to use for small businesses, with pricing set by law, ensuring transparency and cost savings[3][5][6].

Role in the Broader Tech Landscape

SimplyInsured rides the wave of digital transformation in insurance (InsurTech), particularly focusing on the underserved small business segment. The timing is critical as small businesses increasingly demand digital-first, transparent, and efficient solutions to manage complex benefits. Market forces such as rising healthcare costs, regulatory complexity, and the shift to remote and hybrid work models amplify the need for accessible online insurance platforms. SimplyInsured influences the broader ecosystem by setting new standards for customer experience in health insurance purchasing, pushing incumbents toward digital innovation, and enabling small businesses to compete for talent with better benefits[1][2][5].

Quick Take & Future Outlook

Looking ahead, SimplyInsured is poised to expand its market share by deepening integrations with payroll and HR platforms and potentially broadening its product suite beyond health insurance to other employee benefits. Trends like increased regulatory scrutiny, demand for personalized insurance products, and AI-driven customer service will shape its evolution. As the company scales, its influence could extend to reshaping how small businesses manage employee benefits holistically, further reducing friction and cost. SimplyInsured’s mission to eliminate fear from health insurance remains a powerful rallying point as it continues to innovate in a traditionally complex industry[3][5].