Other
Public LinkedIn/Built In commentary references organizational volatility and prior layoffs/turnover concerns, but I did not find a primary-source layoff announcement from SimplyInsured.
SourceWe sell health insurance to small businesses 100% online.
Company research
Public company, workplace, funding, and market signals
Updated Aug 16, 2026
Overview
SimplyInsured is a San Francisco-based insurtech company that helps small businesses compare, buy, and administer health insurance online, with a focus on medical, dental, and vision plans.
Primary product
100% online small business health insurance platform and quote engine
Founded
2012
Headquarters
San Francisco, California, United States
Team size
30-40 employees
Work style
Flexible
Industry
Insurance
Sub-industry
Insurtech / small business health insurance broker
Offices
San Francisco, California, United States
Richmond, California, United States
Business model
B2B2C
brokerage
marketplace
software-enabled insurance distribution
Funding
People & investors
Leadership
CEO & Founder
Co-Founder, Chief Technology Officer / Head of Engineering
Director of Operations and Head of Customer Support
Director of Strategic Partnerships
Co-Founder, Head of Product
VP, Head of Product (former)
Senior Product Manager (former)
Work & culture
Mission-driven, values-based startup culture emphasizing transparency, feedback, bias to action, growth, and dissent; employees are expected to have direct impact and high ownership.
Work style
Flexible
Compensation
No explicit public compensation ranges found in primary sources. Secondary sources suggest startup-style tradeoffs: meaningful mission and flexibility, but compensation may be below larger peers.
Benefits
Publicly emphasized values-based culture
Transparency
Feedback
Bias to action
Growth
Obligation to dissent
Product & market
Pricing
Likely commission-based brokerage and partner-distributed insurance sales; no public pricing page found for direct SaaS pricing.
Differentiators
- —100% online shopping and enrollment experience
- —Unbiased recommendations for small business health insurance
- —Administers plans on-platform to reduce paperwork
- —Embedded distribution via payroll and HR partners
- —Small-business-specific workflow and support
Technology
Rails
React
Redux
CI/CD
automated testing
SQL
Customers
Small businesses
Employers purchasing employee health benefits
Payroll/HR platform partners
Competitors
Zenefits
Gusto (adjacent/partner-competitor depending on offering)
eHealth
NerdWallet (adjacent comparison shopping)
traditional insurance brokers
Scale & contact
Estimated revenue
$10M-$20M annual revenue (Exa estimate), with a specific estimate of about $14M
Estimated monthly visits
14.5K
Traffic estimate as of Jun 2026
Signals & risks
Latest news
Patriot Software · Nov 2025
Patriot announced an integration with SimplyInsured that embeds insurance shopping, enrollment, and payroll deductions inside Patriot Payroll for small businesses.
SimplyInsured LinkedIn · Sep 2025
Recent partnership announcement showing continued embedded-benefits strategy.
SimplyInsured / LinkedIn · Sep 2025
SimplyInsured announced a NetSuite SuitePeople integration so SMBs can manage benefits within NetSuite and automate payroll deductions.
Gusto Embedded · Jan 2024
Gusto Embedded announced SimplyInsured as a health-insurance partner for embedded payroll customers.
TechCrunch · Jun 2015
Series A announcement detailing the platform, lead investor Polaris Partners, and growth plans.
Jobs and careers at SimplyInsured
4 jobs at SimplyInsured
Carrier Submissions Coordinator (Employee Health Insurance)
Remote
Operations
Remote
1w ago
Remote
Full-time
Client Outreach/Onboarding Coordinator
Remote
Operations
Remote
1w ago
Remote
Full-time
Customer Support Representative
Remote
Customer Support
Remote
1w ago
Remote
Full-time
Employer Benefits Account Coordinator
Remote
Operations
Remote
1mo ago
Remote
Full-time