The January/February 2020 edition marks the third time we have pictured an InsurTech founder on the cover of Carrier Management.

Louis Ziskin, the founder of DropIn Inc., was the first in December 2016. Shown holding a drone on a cover that said, “Taking Flight: A New Breed of CEO Rising in InsurTech,” Ziskin embodied the spirit of innovation that resonated through all five InsurTech profiles published in that edition. But he had a very different backstory than two serial entrepreneurs, a young business consultant and a marketing expert featured alongside him. Ziskin, who had been incarcerated for 12 years for his prior involvement in drug trafficking, turned his life around, eventually founding an on-demand live video inspection service for insurance adjusters.

Inaki Berenguer, co-founder of CoverWallet, an engineer from Spain who became a tech entrepreneur, was the subject of our second InsurTech cover profile in January 2019. And for the January/February 2020 cover, the subject is Alex Timm, an actuary who has been involved in insurance since age 14, the co-founder of Root Insurance Company.

New chapters in the stories of each executive were written toward the end of 2019.

Root, the carrier that started providing telematics-based auto insurance delivered through an app in October 2016, moved into the renters insurance market, according to a November announcement.

Also in November 2019, roughly three years after CoverWallet launched, brokerage giant Aon announced that it would buy the digital agency to boost its presence in small and medium-sized business market.

The change for Ziskin’s DropIn is the most recent. “DropIn, Inc. Announces Joseph Shemesh as New CEO” reads the subject line of an email delivered to CM inboxes as this edition when to print in December. Ziskin is stepping down to focus his time primarily on growing a different type of tech company, SuperCall Inc., seemingly unrelated to insurance.

SuperCall is a celebrity video chat application that allows regular folks to video chat with their favorite show business celebrities, athletes, and even business gurus, according to the website. Actress Ashley Benson, known for her role in the TV series “Pretty Little Liars,” video chatted with 50 hospitalized children over Thanksgiving, after gifting 50 iPhone 11 Pros engraved with her signature to them.

More typically, callers pay a fee to the superstars, and that fee is donated to a charity they choose.

What a supercool Idea!

This resonated with us at CM because we know there are superstars in the world of insurance too.

In the January/February 2020 edition, articles featuring a new generation of leaders—Timm, Mitchell Doust of Cover Genius and Nick Shutwell of Clearcover—aim to inspire traditional executives with lessons learned in building their companies. We asked all three to share views on how established insurers need to change. But we’re keen to get the other side.

What does the young generation of insurance professionals want to know from the prior generation? Who would you want to ask? How do you want to interact with them? Should charitable contributions be involved?

What do veteran executives know about the realities of insurance, about mapping out strategies and building cultures, about managing themselves that they would like to share?

While we might not be able to arrange live chats with Warren Buffett and Ajit Jain through an app, there are veteran superstar executives all over the industry—and recently retired ones still doing great things. Webinars, Twitter chats, online and in-person meetups are all possibilities that CM could organize to bring this to life.

Let us hear from you whether you’re new to the business or an established player if you want to participate—and how?

(Feel free to respond in the comments section of this article or email our editors directly at