SimplyInsured took the most dreaded errand a founder runs - buying employee health coverage - and shrank it to about ten minutes online.
The logo glows white on a navy field, which is roughly how it looks at 11pm when a small-business owner finally finds the plan they can afford.
Open Square Payroll. Click "add health benefits." A clean flow appears, asks a handful of questions, and shows you real plans with real prices. Most people never see the name behind it. That name is SimplyInsured.
Today the company is less a website you visit and more a layer you pass through. It runs the health-insurance experience embedded inside Square, Gusto, Check, and Patriot payroll - the carrier-neutral plumbing that turns "I should probably offer benefits" into a finished enrollment. It also still operates its own marketplace at simplyinsured.com, where a small business can compare medical, dental, and vision plans from more than 200 carriers and sign up without ever picking up a phone.
That sentence sounds modest. In the small-business insurance world, it is closer to heresy.
Here is the thing nobody at a carrier will admit out loud: complexity is a feature. The harder a plan is to compare, the less likely you are to notice you are overpaying. For a business with three employees and no HR department, "shopping" for health insurance has historically meant phone tag with a broker, spreadsheets that don't match, and a quote that arrives next week - if it arrives at all.
Small-business health insurance is roughly a $20 billion corner of the economy, and for years it ran on fax machines and patience. The people buying it - founders, shop owners, clinic managers - are exactly the people with the least time to decode it.
Fear is the right word. The dread isn't only about money. It's about choosing wrong on behalf of people who trust you, and not being sure you even understood the choice.
SimplyInsured was started in 2012 by Vivek Shah and Bob Aspell, both MIT electrical-engineering and computer-science grads. Shah had been a healthcare analyst at McKinsey, working with insurance companies on efficiency - which is a polite way of saying he had seen exactly how the sausage was made. The founding spark, by his own account, was personal: a confusing experience trying to buy his own health insurance on the open market.
The bet was simple, and slightly insulting to the incumbents. If you could get a real quote online for a flight, a car, or a mortgage, why not for a health plan? The wager wasn't on a new kind of insurance. It was on the radical idea that the buying process itself could be honest, fast, and free of a salesperson breathing down your neck.
It's a low bar. That it counts as a differentiator tells you everything about the industry they walked into.
A timeline with exactly one entry that isn't a year. Startups are funny about deadlines.
The marketplace is the part people see. Answer a few questions, and every plan available in your area gets quoted at once, side by side, so you can actually sort by price and coverage instead of vibes. Enrollment for a small team usually takes around ten minutes.
The administration platform is the part that matters more. Once you've enrolled, the SimplyInsured dashboard handles the unglamorous machinery: adding and removing employees with one click, syncing contributions and deductions to payroll every pay run, untangling invoices, and setting up HSAs and FSAs. The promise isn't excitement. It's that you stop thinking about it.
Real quotes from 200+ carriers in seconds. Medical, dental, and vision, compared side by side.
One-click employee changes, automated deductions, taxes, HSAs/FSAs, and human-readable invoices.
One-click integrations that push contributions and deductions to payroll on every run.
White-label benefits living inside Square, Gusto, Check, and Patriot - same engine, partner's logo.
The business model is the oldest one in insurance - broker commissions paid by carriers - just without the phone tag. The software is new. The economics are ancient. That combination is why it can be free to the people using it.
The company reports more than 25,000 small businesses insured through the platform and over $50 million in total savings generated for them. It raised about $8.5 million across its seed and Series A rounds - lean by modern standards, which fits a company whose whole pitch is doing more with less friction.
Four numbers a founder can read at a glance, which is the only attention span insurance ever gets.
The Series A bar dwarfs the seed bar, then the total dwarfs them both. Math, doing what math does.
The partnerships are the real evidence. When Square Payroll decided to add benefits in 2018, it didn't build its own insurance stack - it plugged in SimplyInsured. Gusto Embedded, Check, and Patriot followed similar logic. For payroll companies, health insurance is a swamp of regulation and carrier relationships. SimplyInsured is the bridge they rent instead of build.
Internally, SimplyInsured leans data-driven and unusually open: salaries and equity are discussed in the open, feedback is constant, and there's a stated "obligation to dissent" - the expectation that you'll challenge a decision you disagree with rather than nod along. It's a culture that mirrors the product. A company built to remove fog from insurance has, sensibly, tried to remove fog from itself.
The mission has stayed fixed since the first year: eliminate fear from health insurance. Not lower it, not manage it - eliminate it. That's an ambitious verb for an industry that mostly traffics in fine print.
The future SimplyInsured is building toward is one where buying employee health coverage stops being an event. No broker, no fax, no week of waiting - just a step inside software you already opened for another reason. As more payroll and HR platforms embed benefits, the company's bet is that the best insurance experience is the one that disappears into the tools small businesses already trust.
There are real questions ahead. Embedded distribution means competing with - and depending on - the platforms it powers. Carriers, regulation, and the unglamorous grind of health policy don't simplify on command. But the direction is clear, and the industry it's nudging is not known for moving quickly.
So return to that small-business owner at 11pm, the one staring at Square Payroll and dreading the words "health benefits." A few years ago, that click opened a swamp. Now it opens a flow that quotes 200 carriers, names a price, and syncs the deductions before they finish their coffee. They still may never learn the name SimplyInsured. That, more than any funding round, is the point.