Case Study: How Assured CEO Justin-Lewis Weber Leveraged "Network Learning" To Find Product-Market Fit As A Insurance Tech Startup

Learn how Justin smartly leveraged his professional and investor network to rapidly learn about the insurance industry and disrupt it with Assured.

Nov 02, 2020

The Problem - Innovating While Lacking Domain Knowledge
Justin Lewis-Weber came into the insurance industry with no prior background or domain expertise. “Book learning” turned out not be enough in gaining the knowledge he needed to make an impact as an insurance tech startup.
The Solution - Using “Network Learning” To Rapidly Get Up To Speed
Lewis-Weber had to rely on his immediate professional network, and when that wasn’t enough, he tapped his investors’ Rolodex to find experienced insurance practioners.
The Takeaway - Your Credibility = Your Network + Ability To Recruit Top Talent
Through leveraging his network and startup’s capital, Lewis-Weber was able to hire a well-respected insurance sales executive, which you can find more details in Assured’s Founder File below.

Assured’s Founder File: How to Hire Experienced Sales Executives

Justin’s Email To Contact Him: justin@assured.claims

I got the chance to speak with Justin Lewis-Weber, co-founder and CEO of Assured, about how he’s approached finding product-market fit in the insurance tech industry.

Assured aims to disrupt the trillion-dollar insurance industry by modernizing its most archaic component: claims. Currently, 300,000 claims adjusters spend their days talking on the phone and typing into unstructured text fields. We can do better—by combining logic, inference, and modern computer vision tools, we're able to both increase efficiency and improve customer satisfaction. By rearchitecting how the underlying information is ingested and stored, they're poised to transform the very nature of insurance.

Assured cofounders Justin Lewis-Weber (left) and Theo Platt (right).

The Problem: Innovating While Lacking Domain Knowledge

What was the toughest problem you’ve solved recently to achieve product-market fit?

With Assured, I was entering a market I knew relatively little about - auto insurance (specifically, claims to process). My background is Aerospace Engineering and Radio Physics, and my previous companies have all been in the hard-tech spaces. Although deep in software, my cofounder had not built “big enterprise” SaaS before (targeting the Fortune 100).

Neither of us had any experience in insurance despise personally owning auto insurance. Still, we came to wholeheartedly subscribe to a set of theses that we believed could revolutionize auto insurance.

Describe the nature of the problem. What are the critical constraints?

Our lack of experience in the industry was problematic for three primary reasons:

Refining product theses
Lack of industry vernacular and credibility
Lack of top-of-funnel leads in the sales process.

We could take two major approaches: solving the problem with “book learning,” or solving the problem by “people/network learning.”

In general, I’m a huge fan of “book learning,” where one seeks out existing structured knowledge on the topic. It’s how I’ve started building my past companies. However, the insurance space's structured knowledge is often incomplete and obfuscated behind NDAs and best practices “everyone knows.” Therefore, I quickly exhausted this strategy and turned to “network learning,” where I looked to people who have experience in the space to absorb knowledge.

What was your initial thought process in solving the problem?

Once it was clear that people learning was the way to go, the natural first step was to reach out to my network. I did this in two ways.

First, I asked some of my closer contacts who I intuitively thought had a reasonable probability of being connected in the space. I’d put this at about 20 initial nodes and people I was truly close with, so I didn’t feel like I was burning social capital.

Second, I did some LinkedIn searches for the types of folks who I thought could answer my questions (in this case, COO, CTO, VP Claims, VP Innovation) at insurance carriers and tried to find second-degree connections. Or, even better, people who seemed to be second-degree connections to many of the types of people I wanted to get into contact with. I also sent a few of these LinkedIn contacts to the group mentioned above to see if they had any second degrees.

The Solution: Using “Network Learning” To Rapidly Get Up To Speed

How did you evaluate your initial solution(s) before trying to implement them?

It was slow going at first. From my list of close contacts, I got three solid industry connections. Unfortunately, neither panned out long term; however, both were extremely valuable in the “refining the Assured theses” part of the problem.

One of the connections was able to introduce me to a potential client, a Head of Innovation at one of CA’s largest auto carriers. Over several phone conversations with him, I learned a ton more about the space and refined the Assured thesis into basically what it is today. He also helped me dramatically enhance my insurance vernacular, which was imperative to have credibility in the space. However, that person has yet to buy from Assured (as that company’s new CEO has put a kibosh on any new claims initiatives). Equally unfortunate, I quickly understood the dynamic that although this person knew many peers (similar roles at other companies) that would be extremely valuable intros for me, it was not an industry norm to introduce vendors across companies like this. So that connection ended up being a dead end.

The other two connections ended similarly.

When you were working to implement them, what else did you discover that either confirmed you were on the right track or opened your eyes to a new facet of the problem?

Although those first round of connections didn’t end up yielding this expanding network I wanted, one of those connections was able to get me (physically) into a claims center, where I was able to see firsthand the current set of processes. This was invaluable in refining the thesis and gave me a fair amount of credibility in the space. It also directly influenced Assured’s first product.

The next major strategy I tried was utilizing investors as a resource. During this intervening time, Assured raised a seed round. I was intentional when constructing the cap table to not only seek out SV investors but also other investors (such as family offices or angels) with deep “old money” ties into the insurance space. Once the round was closed, I was transparent in asking those investors for high-level introductions to folks in the industry. We’re talking about the Chairman of XYZ Fortune 50 insurer. These ended up yielding some great connections, and these introductions and relationships with executives were surprising non-transactional. I helped hammer that home by making this much more “young guy (former Stanford) seeking advice” as opposed to “software vendor trying to sell you something.”

When did you realize that you arrived at the right solution to acquiring InsurTech domain knowledge, which helped you establish product-market fit?

The right solution ended up being the above (leaning on investors with deep connections), plus hiring an experienced Head of Sales. We leaned on some executive recruiters (recommended by our investors) and were lucky enough to make a truly bullseye 10/10 perfect hire.

The Head of Sales we hired was a 30-year industry veteran selling software into insurers (perfect!), but energetic/adventurous/humble enough to be totally at home in an early-stage startup working for two founders under 22 years of age. We truly lucked out here.

With this key hire, we became immediately more credible to customers, investors, and advisors. Still, the hire came with a massive amount of experience targeting these customers and relationships in the space. Insurance is a very small world, so this went a long way.

In terms of top-of-funnel sales leads, we went from 1-2 companies (granted, multi-billion-dollar companies, but still) in top of the funnel at a time to 8-10.

The Takeaway: Your Credibility = Your Network + Ability To Recruit Top Talent

Did that solution come with its caveats or tradeoffs? If so, what are they?

Of course. Hiring an experienced Head of Sales was time-consuming and expensive (easily 2-3 engineering hires worth of cash on comp and recruiters). However, this was the right decision, because, without close customers, it didn’t matter how good our product was.

What is your general advice for founders to face the challenges related to product-market fit in your space?

I’d say that going into Fintech without domain experience is a hard mountain to climb but would generally be worth it. Finding champions in potential customers who can mentor you to the correct set of theses, then eventually PMF, would be ideal. These champions will also likely help you close your round (nothing is more convincing to seed-stage investors than large prospective customers singing the praises of your solution).

If the above fails, pony up and pay for an industry veteran to join the team. Of course, it’s not as simple as just forking over a load of cash—convincing such a veteran (and making sure they’re a culture fit, etc.) is a huge challenge and a major time and energy sink. But, when taking on old and archaic industries, you need the insight and network that veterans bring.

Name three other people I should profile next for F2F Case Studies.

Alex Zhuk, Founder of Cloud Agronomics: Cloud Agronomics is the agricultural intelligence engine.
Zach Oschin, Founder of Elenas: Elenas is building the first social commerce platform for consumer products ($260 billion USD market in relevant categories) in LATAM.
Josh Browder, Founder of Do Not Pay: Do Not Pay is the world's first robot lawyer. Helping millions of consumers solve their problems for free.

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