The View from the Office.

I met up with Jeff Cohen, senior vice president at Zywave, for lunch at the Bryant Park Grill. He had the chicken cobb salad and an unsweetened iced tea. I had the mushroom ravioli. We hesitated, but didn’t turn down the bread and olive oil.

I first met Jeff in the late 1990s when we were both working for Bloomberg. At the time he was head of sales in New York. I was in charge of News for the Americas. We would get coffee to share notes on how to better serve clients.

After losing touch for a couple decades, we reconnected a few years ago and now we text and email to share observations about technology, markets and how the world has changed for the better and the worse over the past quarter century.

Jeff has great perspective about leadership and management, in particular how it is reflected in sales organizations. He is concerned that in an era of remote work post Covid where Zoom is the default we are losing the ability to connect with people.

He encourages sales reps at Zywave to pick up the phone and call their clients or get out of the office and visit them. We met shortly after he got off the plane from his 36th flight this year. He’s on the road constantly to meet customers.

At Zywave, he said he’s known for “the unscheduled reach out,” which is pretty much what it sounds like, an unannounced phone call or a Teams video meeting.

He said it’s important to connect with people and talk about more than business. He books his calendar in 25-minute increments to leave extra time for chitchat.

He is excited by how AI can accelerate projects but he draws a distinction between how AI can make us efficient i.e. allowing us to text a reservation from a plane and getting home earlier versus productive, which is actually accomplishing more.

Jeff is a fan of LinkedIn and said that it was a red flag to him once when the company hired someone who didn’t have a LinkedIn profile. He regards the platform as essential for networking and connecting with prospects.

Zywave sells software and data to the insurance industry. Most of our conversation focused on AI, in particular how it’s impacting the insurance industry.

Jeff said insurers are facing a category of AI risk they haven’t priced before. If you insure AI, you are insuring things machines did. But humans trained the machines. It’s not clear who is responsible and it’s not clear what courts will say.

Jeff pointed to a 2024 case where a customer was told by an Air Canada chatbot in advance that he would receive a bereavement refund that never materialized. He sued and won.

As all of us use AI agents to execute commands, Jeff’s predicting that another crop of insurance carriers will rise up to cover these new frontier risks. And that’s how the insurance marketplace evolves.

You can connect with Jeff via LinkedIn or DM me for a warm intro.