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Founded Year



Series A | Alive

Total Raised


Last Raised

$5.9M | 8 yrs ago

About SimplyInsured

SimplyInsured is a health insurance marketplace and administrative platform for small businesses. It analyzes thousands of insurance policies to find the coverage, price, and value for every situation, and provides those options on a single site. It was founded in 2012 and is based in Richmond, California.

Headquarters Location

4909 Central Avenue Unit B5

Richmond, California, 94804,

United States




Expert Collections containing SimplyInsured

Expert Collections are analyst-curated lists that highlight the companies you need to know in the most important technology spaces.

SimplyInsured is included in 5 Expert Collections, including HR Tech.


HR Tech

4,043 items

The HR tech collection includes software vendors that enable companies to develop, hire, manage, and pay their workforces. Focus areas include benefits, compensation, engagement, EORs & PEOs, HRIS & HRMS, learning & development, payroll, talent acquisition, and talent management.


SMB Fintech

2,003 items



2,967 items

Companies and startups that use of technology to improve core and ancillary insurance operations. Companies in this collection are creating new product architectures, improving underwriting models, accelerating claims and creating a better customer experience



8,123 items

Companies and startups in this collection provide technology to streamline, improve, and transform financial services, products, and operations for individuals and businesses.


Digital Health

10,585 items

The digital health collection includes vendors developing software, platforms, sensor & robotic hardware, health data infrastructure, and tech-enabled services in healthcare. The list excludes pureplay pharma/biopharma, sequencing instruments, gene editing, and assistive tech.

Latest SimplyInsured News

QuickBooks Payroll vs. Square Payroll: Pricing, Features, Pros & Cons

Jul 5, 2023

QuickBooks Online Payroll pricing Starting price: $45 per month + $5 per employee per month Intuit QuickBooks Payroll is a cloud-based payroll processing service from Intuit, one of the top financial software services in the U.S. and across the globe. QuickBooks Payroll has three payroll plans. While all three plans share the same full-service payroll features, they come with different levels of customer support and integrations: QuickBooks Payroll Core starts at $45 per month plus $5 per employee per month. QuickBooks Payroll Premium starts at $75 per month plus $8 per employee per month. QuickBooks Payroll Elite costs $125 per month plus $10 per employee per month. QuickBooks Online Payroll also charges some additional fees: Multi-state payroll tax filing costs $12 per state per month for the Core and Premium plans. Workers’ compensation administration costs an extra $5 per month for the Core plan only. Integrating your employee benefits and workers’ compensation insurance with your payroll plan costs an additional unspecified monthly fee. Direct deposit for contractors costs an additional fee of $5 per month. If you’re new to QuickBooks Online Payroll, you can choose to get 50% off your payroll plan’s base price for your first three months of service, or you can sign up for a 30-day free trial. Note that the free trial requires you to enter your credit card to sign up, and once the trial expires, you’ll be charged the monthly fee automatically unless you cancel in advance. Starting price (contractor plan): $0 per month + $6 per contractor per month Square Payroll is an online payroll service that belongs to the Square suite of products, which also includes Square Point of Sale, the Cash App and Square Teams. Square Payroll starts at $6 per person paid per month, which makes it one of the most affordable payroll options for small-business owners who only pay contractors. Square Payroll has two plans, both with the same full-service payroll features: Square’s contractor payroll plan costs $6 per contractor paid. Square’s employee and contractor payroll plan costs $35 plus $6 per contractor paid. While Square Payroll doesn’t advertise a free trial, it doesn’t cost anything to set up an account or enter your employees’ pay information. You won’t be charged until you run payroll for the first time. QuickBooks Online Payroll vs. Square Payroll: Average monthly costs Even though Square Payroll’s starting monthly price is $5 cheaper than QuickBooks Payroll’s, its higher per-payee price means QuickBooks Payroll costs less per month for employers with 11 or more workers. Note that the cost comparison table below doesn’t account for QuickBooks Online Payroll’s free trial or 50% off discount, nor does it consider any of QuickBooks’ extra fees (including those for direct deposit and benefits administration). 1 payee In contrast to top payroll brands like Paychex Flex, both QuickBooks Payroll and Square Payroll include end-of-year 1099 tax form preparation and filing at no additional cost. (QuickBooks charges a typical industry-standard fee if you want the company to print and mail Form 1099 on your behalf, but contractors can access the form online at no cost.) However, Square has a slight edge over QuickBooks in terms of extra fees and flexibility. For instance, Square Payroll includes multi-state payroll free with both plans while QuickBooks Payroll charges a monthly fee of $12 per additional state. QuickBooks charges an extra monthly fee for business owners to pay contractors through direct deposit. (Employee direct deposit is included free.) At the same time, it’s worth noting that Square Payroll cannot pay local taxes — it offers only state and federal tax filing. QuickBooks Payroll includes local tax filing with its two higher-tier plans, but the feature isn’t offered with QuickBooks Payroll Core. Employee benefits administration Winner: Tie Both QuickBooks Online Payroll and Square Payroll offer optional health insurance benefits through SimplyInsured. Additionally, both payroll providers let you integrate health benefits with payroll, which means the software makes automatic insurance premium deductions from employee paychecks (though QuickBooks Payroll charges an extra fee for integration). SimplyInsured is available in every state except Hawaii, Vermont and Washington, D.C. If you have employees in those states and would prefer to find health insurance through your payroll provider, OnPay, ADP and Paychex offer benefits in all 50 states. Time-tracking tools Winner: Square Payroll While Intuit’s accounting software program, QuickBooks Online, integrates with more than 700 third-party apps (including payroll programs like ADP), Intuit QuickBooks Payroll integrates with relatively few products besides QuickBooks Time and QuickBooks Online. Worse, QuickBooks Payroll Core doesn’t include free QuickBooks Time access or integration. QuickBooks Core users with hourly employees will have to purchase a separate QuickBooks Time subscription, find a third-party workaround to integrate both services or enter employees’ hours by hand. With Square, on the other hand, payroll software users get free access to Square’s time-tracking software, Square Shifts. You can choose to upgrade to Square Shifts Plus for more labor management features, but the free version of Square Shifts that’s available to payroll users includes shift scheduling, direct tip tracking, time cards, overtime and break tracking and more. Scalability Winner: QuickBooks Payroll Square Payroll excels at simplicity. What you see with each plan is exactly what you get, which makes Square ideal for first-time employers, employers with one or two workers and business owners who pay employees from their mobile phones. But if you want multiple plan options, QuickBooks Online Payroll is the clear choice over Square. While it doesn’t have a cheap contractors-only option, QuickBooks Payroll’s three plans ensure employers can access more customer support and payroll features as their teams grow without having to switch payroll providers. Direct deposit Winner: QuickBooks Payroll Even though QuickBooks Payroll charges extra for contractor direct deposit, its next-day (for Payroll Core) and same-day (for Payroll Premium and Elite) direct deposit feature handily beats out Square Payroll’s standard four-day direct deposit. However, Square Payroll has an on-demand pay option for employees in the form of the Cash App, meaning employees can secure direct access to their funds on their own schedules. QuickBooks Payroll supports direct deposit and paper check payment options, but it lacks an on-demand payment tool. QuickBooks Payroll pros and cons QuickBooks Payroll pros Below-average per-payee price lowers costs. Built-in time tracking (not available with cheapest plan). Some HR features with higher-tier plans, including HR support center access. Next-day or same-day direct deposit, depending on plan. QuickBooks Payroll cons Additional fees for benefits administration and direct deposit. Less fully featured than most competitors, notably Gusto. Limited human resource tools. Square Payroll pros Below-average base price for employee payroll plan. No base price for contractor payroll plan. Optional healthcare benefits and workers’ compensation insurance. Excellent apps for on-the-go payroll processing. Square Payroll cons Limited reports, especially compared to QuickBooks Payroll and Paychex Flex. Three accounting integrations only (QuickBooks Online, Zoho Books and Xero). No hiring tools. Our methodology To compare Square Payroll and QuickBooks Payroll, we set up free accounts with both payroll providers so we could test their software for ourselves. We also reviewed each payroll company’s websites, including any available white papers, demos and product specs. We also considered reviews from users on third-party sites like Google Play, the App Store, the BBB and Consumer Affairs. To generate our star ratings for each brand, we assessed how well each brand stacked up according to the following payroll criteria: Pricing and plan data. Customer service. We also took our expert’s experience with the software and professional opinion under consideration. Learn more about how we calculate our star ratings, including how we weighted each subcategory to calculate scores with our internal algorithm. Should your business use QuickBooks Payroll or Square Payroll? Both QuickBooks Payroll and Square Payroll are among the best payroll processing systems for small, midsize and some large businesses. The right one for you depends largely on your payroll needs and budget. If you work mainly with independent contractors, already use Square Point of Sale or need payroll essentials only, Square Payroll could be a good fit for you. It bundles all the essential payroll features with basic benefits administration at a comparatively affordable price. If your organization works with both contractors and W-2 employees, has complex payroll and accounting needs, or already uses QuickBooks Online, QuickBooks Payroll is a solid — if pricier — payroll option than Square. Didn’t find your ideal payroll software match with either QuickBooks Payroll or Square Payroll? Consider the following alternatives: Gusto for all-in-one payroll and basic HR software. ADP for comprehensive workforce management. We review these three brands and more in our Best Payroll Software piece . 1 OnPay

SimplyInsured Frequently Asked Questions (FAQ)

  • When was SimplyInsured founded?

    SimplyInsured was founded in 2012.

  • Where is SimplyInsured's headquarters?

    SimplyInsured's headquarters is located at 4909 Central Avenue, Richmond.

  • What is SimplyInsured's latest funding round?

    SimplyInsured's latest funding round is Series A.

  • How much did SimplyInsured raise?

    SimplyInsured raised a total of $8.42M.

  • Who are the investors of SimplyInsured?

    Investors of SimplyInsured include AltaIR Capital, Corazon Capital, Bessemer Venture Partners, Polaris Partners, Y Combinator and 12 more.

  • Who are SimplyInsured's competitors?

    Competitors of SimplyInsured include Mylo and 5 more.


Compare SimplyInsured to Competitors

Stride Health

Stride Health is a health insurance recommendation application. It builds a health profile for each patient, then delivers financial forecasts. Its algorithm filters to find a recommendation with preferred doctors, and prescription drugs. The company was founded in 2014 and is based in San Francisco, California.

Buoy Health Logo
Buoy Health

Buoy Health develops a digital health platform to provide a personalized symptom checker. It offers an artificial intelligence and advanced machine learning-based application to check users' symptoms in combination with the latest medical information to provide personalized information on possible causes and treatments for illness. It was formerly known as QUR. The company was founded in 2014 and is based in Boston, Massachusetts.

Sidecar Health Logo
Sidecar Health

Sidecar Health focuses on the health insurance industry. It offers modern, consumer-driven health insurance plans that provide transparency and control over costs and choices. The company primarily serves individuals, families, and employers. It was founded in 2018 and is based in El Segundo, California.


League operates as a digital health platform. It delivers high-engagement, personalized healthcare experiences for consumers and helps people to use solutions powered by League to access, navigate, and pay for care.It was founded in 2014 and is based in Toronto, Canada.

Lumity Logo

Lumity is a company that focuses on providing modern solutions for benefits management in the human resources technology sector. The company offers a data-driven, carrier-agnostic approach to benefits management, providing an online benefits portal, year-round support, and assistance with PEO migration. Lumity primarily serves high-growth tech companies. It was founded in 2014 and is based in San Mateo, California.

Snapsheet Logo

Snapsheet specializes in insurance technology solutions. It enables a claim process starting with virtual estimations all the way to final repairs and payment, by generating communication between consumers, shops, and carriers. The company offers a range of services including appraisals, claims management, and payments, all aimed at managing the insurance claims process. It primarily serves the insurance industry. It was founded in 2011 and is based in Chicago, Illinois.


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