What if employee benefits just made sense and were as simple as cash? Meet Level.

Jana Messerschmidt
Lightspeed Venture Partners
5 min readApr 16, 2021

Announcing Lightspeed’s Series A investment in Level

Paul Aaron, Level Founder & CEO

I met Paul Aaron through Diogo Monico in early 2018. I had recently invested in Diogo’s company, Anchorage, as part of #ANGELS. He asked if I’d be interested in another fabulous founder friend of his from Square. Having grown up in the house of Jack Dorsey myself at Twitter, I said “Absolutely!” before even asking what he was building.

Fast forward to my first meeting with Paul. I had limited context other than he was one of the first 20 employees at Square and was working on something game-changing in the fintech space.

“We’re making benefits as simple as cash,” he explained. At first, it wasn’t abundantly clear how employer benefits can be a fintech problem. But as Paul articulated such an acute set of pain points for employers and employees, and the vision for unlocking more value from benefits through seamless payments — I fought my way into angel investing in Level on the spot.

Why benefits, why now

Employers are taking bigger roles in their team’s wellness, often in the form of benefits. In fact about 160 million Americans — nearly 50% — rely on their employer to get important benefits like health insurance, dental and vision, and more.

As an employee in a company, we are all consumers of these benefits products — medical is mandatory, large and complex. And then there’s the world of voluntary benefits including dental, vision, pre-tax, 401k, fertility, mental health, gym reimbursement, wellness, child services, the list goes on.

However, consumers can run into a multitude of problems trying to use these benefits.

Let’s break down some of those for just dental and vision alone, which is what Level is tackling first.

  • Who, what, and where’s my insurance? Who can remember the vendor for each benefit? You likely check an employee benefits intranet site, if one exists. Or if you lost your member ID card forget it: You end up emailing HR to get a new one.
  • Time for a visit. Where can I go? Networks are confusing and restrictive. What if my kids’ favorite dentist is now out of network? How do I even find a new one that’s good?
  • What’s this going to cost me? There are copays, and deductibles, and in network and out of network rates, but you need the appointment so you just wing it and hope for the best.
  • What’s this bill in the mail? It says it isn’t a bill but says you owe money. But you don’t stress because it is not a bill. But then you get the paper bill in the mail and it’s even more. “Why do I owe this?! I thought I had insurance!!”
  • Mail a check. Really? Isn’t this 2021? Good luck finding your checkbook and a stamp. Or just submit your credit card info over the payment portal that looks like it is from the 90s.
  • Where’d my time go? Finally, you huff and puff while blaming your employer and HR for bad benefits coverage and for wasting hours of time.
  • And then there’s dependents. Multiply all of this by 10 when it is your spouse / dependent trying to use a benefit.

How Level makes paying with insurance simple and easy

It doesn’t have to be like this. Enter Level: a fintech company who aims to rebuild benefits, starting with dental and vision, with a laser focus on the consumer (i.e. employee) experience.

Companies like Slack and Dropbox were the consumerization of the enterprise. Robinhood consumerized finance. Level will consumerize the $100B+ benefits space.

Paul Aaron, a truly special founder, has the perfect background of fintech (Square) and insurtech (Oscar) and the grit and tenacity to tackle this complex problem. He’s recruited an outstanding team from Square, Oscar, Uber and Google to name a few.

Straightforward products

With Level, plans are just plain simple. Everything’s covered 100% and there’s no copays or deductibles to worry about. Plus, you can see any provider you want, even out of network providers are covered 100%. As a result, Level members keep more money in their pockets: 86% of Level members don’t pay anything out of pocket, compared to 55% of members on traditional plans.

A slick mobile-app

Level also comes with a mobile app so you can manage your total benefits balance and spend from the palm of your hand. Find a provider, get cost estimates, view your remaining balance, and even make payments in real-time. No more paperwork, bills, or checks. Everything’s simple and easy.

Benefits, consumerized: The Level employee experience

Employers can stand out by offering Level

HR leaders are always looking for ways to take care of their teams through better benefits. With an experience like Level, employers help their people have the freedom to get the care they need, save money, and save time. Once people have experienced the Level app, they’ll start asking their employers to offer it.

HR leaders and teams tremendously benefit from Level. Not only do they save time (no longer answering “lost ID card” questions), they can save at least 20% on their benefits budgets by switching to Level’s innovative self-funded products. With Level, HR leaders can offer the dental and vision benefits they always wanted — adult orthodontia, Lasik, and more. Self-funding enables employers to offer bigger benefits in a much more cost-effective way. My friends at First Round Capital experienced just this.

Excited to bring the vision to life

Fast forward once again … after the angel investment in Level, I joined Lightspeed Venture Partners. I knew that I wanted to invest in Level again, but with even bigger dollars. This was such a big vision (pun intended) and big market, it was going to be a decade+ journey.

Today, I’m pleased to announce that I’m joining Level’s cap table (again!) with Lightspeed’s investment in the Series A. I’m thrilled to join long time friends Rob Hayes (First Round), Satya Patel (Homebrew), Claire Hughes Johnson (COO, Stripe), Operator Collective, and new friend Samir Kaul (Khosla) and many other strategic angels in the round.

Paul, thanks for picking me (twice!) to join you on this ride. It has been phenomenal building the team, strategizing on GTM and talking on the phone at unacceptable-to-most hours.

To quote the reverse of Brett Favre, you’re on the one yard line and I’m excited to be here for the next 99 yards.

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Jana Messerschmidt
Lightspeed Venture Partners

#ANGELS cofounder. Former builder of @Netflix and @Twitter. Proud alum of @eceUIUC.