Connections That Move the Needle

This holiday special ran longer than planned, as Gilad admitted, and began with a tangent about lighting, chocolate babka from a bakery Jay always brings when Gilad visits New York, and who has more mutual LinkedIn connections with whom (Gilad and Jay have 813; Gilad has about 1,590 with Matteo Carbone and about 1,320 with Caribou Honig).

About Jay Weintraub

Jay Weintraub is co-founder and CEO of InsureTech Connect (ITC), the annual conference launched in 2016 that had grown, by its fourth year, to about 7,000 people from over 60 countries.

How ITC Started

In 2015, Caribou Honig, a founding partner of QED Investors with growing interest in insurance technology, was looking for a show to attend and couldn’t find one. He asked a colleague whether they should start one, and the colleague said he knew a guy: Jay. Jay had been launching events since 2008, starting with LeadsCon, a show on internet advertising, customer acquisition and lead generation. Insurance agency owners kept showing up, which got him curious about the industry and eventually made him want to build a show for insurance itself.

What Jay is proudest of, he said, isn’t the attendance but the connections: people who leave inspired, and meetings that move the needle and ultimately affect policyholders’ lives. The one thing he doesn’t want is “innovation tourism,” a term Gilad has used. His own start was in customer acquisition, which broadened to the whole value chain, and the appeal for him is that you can pick any part of it, from claims to new product development, geography expansion, strategic investing and internal innovation, and find something big and complex.

2020 and Hopes for 2021

For Jay, 2020 was crushing because not being able to gather in person hurt, but there was a choice between curling up in a ball and looking for opportunity. The industry was validated, digital moved faster, and the team created the ITC World Tour: 35 stops across the US and the globe, to show that ITC is both local and global, with Gilad producing the India stop in Southern California. ITC Global had 12,000 registrations and thousands of one-on-one meetings, and yet it showed there is no real substitute for getting together.

Jay’s wishful thinking is seeing everyone in Las Vegas on October 4, 2021, with a venue change from the MGM to Mandalay Bay. One prediction he hadn’t expected: the digital pure plays continued to grow and the IPO market took off, and while he’s thrilled with the validation, he wants to make sure the next idea that could become the next Hippo still gets enough sunlight to grow.

Where Is the Business Done at ITC?

Jay’s short answer was everywhere. He told of an AmFam Ventures leader who, when asked how much time he spent on the digital event, didn’t want to answer, because at ITC he meets his portfolio companies, other members of the AmFam organization and other VCs, and rarely new startups. AmFam held its president’s meeting at ITC with about 75 top people. Deals happen through many touchpoints: a booth, a seat next to someone, an accidental dinner invitation, a craps table.

Business Development 101

Gilad asked for a primer on building relationships. Jay’s points:

• Why there is no attendee list: ITC invests in technology to surface connections, but doesn’t hand out the attendee list, because 40 companies hitting the same 20 targets kills their appetite to take meetings. It is bullish on 15-minute one-to-ones, enough to get a feel and decide whether to meet again.
• Insurers need a process: the most advanced insurers have a process for articulating what the organization wants and needs, testing new partners and helping the organization see value, without which a great relationship won’t reach production.
• Startups should not spam: don’t send 100 people the same “do you want to meet?” Put in the research. “I read this report and heard your exec mention this strategic priority, here’s how I can help, can we have 15 minutes?” is a lift but gets a better meeting. Start small, ask a friend for an introduction, and don’t pull people in by the lanyard at a booth.
• After hours: host an interesting dinner with a speaker, not a table of four where you’ll be pitched all night.

Jay cited Milliman as a model. Beyond the stage, it looked at who was there, who it knew, and the message to craft, with a personal reason to meet. People, he said, don’t pick the best product; they pick someone who solves their problem. Gilad added the point about cheap talk: the more detail, the more value.

Long Sales Cycles

Selling into insurers is a long cycle, so it takes time and trust. Insurers have existed hundreds of years and want to know you’ll be around next year, so startups shouldn’t come across as needing a deal now; repeated, credible touches, such as being seen on LinkedIn or in the news, add up. He gave the example of Hover: in year one it met AmFam and got its first institutional investment, in year two Travelers was nearly ready to pack up but kept a meeting on the books, and two years later the head of claims at Travelers was on ITC’s stage describing how Hover improved policyholders’ experience. A four-year cycle. Even Lemonade’s Daniel Schreiber was on stage in 2016, four years before its IPO, which Jay said is super fast. Rocket ships look quick but take enormous effort to break free of gravity.

Gilad agreed that founders from outside the industry often think a SaaS sale will wrap in six to twelve months, when it can take two to four years including approvals and pilots.

How to Test Without Waiting for Perfect

Asked which lesser-known companies insurers should know, Jay declined to name names, and said the mindset matters more: define the problem and desired outcomes first, since even a great demo (he recalled one by Uncork) means nothing unless you have a problem it solves. Insurers should break problems into solvable steps and not be afraid to test a company that may not be around in the future, because the speed of learning is valuable, and if you insist on a partner for ten-year projects, you won’t make progress. He noted some problems, like single entry for multiple submissions, where “the juice isn’t worth the squeeze,” and said an insurer that says it isn’t thinking about machine learning at all has the wrong answer.

Advice: Family Memories, Crucial Conversations, and Hallmark Movies

Jay said lockdown showed him what putting family first really means: his seven-year-old daughter often appears on calls, and he treasures memories he’d never otherwise have. His book is Crucial Conversations, which he has read about a third of, and he reads a lot of fiction: he’d just finished Ready Player Two, is slowly working through Stranger in a Strange Land, and has a not-so-secret indulgence in Hallmark movies. Gilad recommended the Israeli series False Flag.

Key Takeaways

• ITC began when Caribou Honig couldn’t find an insurtech show and Jay, who had run LeadsCon since 2008, built it with him.
• Jay’s goal is connections that move the needle, not innovation tourism, and he doesn’t release attendee lists to protect attendees from spam.
• Insurers need an internal process for stating needs and testing partners, or relationships won’t reach production.
• Startups should research and personalize outreach, lean on introductions, and avoid acting as though they need a deal immediately.
• Cycles are long: Hover’s journey from first meeting to Travelers’ claims head on stage took about four years.
• Insurers should define the problem first, break it into solvable pieces, and be willing to test small or early-stage companies.
• 2020 validated digital in insurance; the ITC World Tour had 35 stops and 12,000 registered for ITC Global.