The String and Key Crew: Josh Weintraub

As part of our ongoing employee spotlight series, we’ll be profiling colleagues who inspire us. Today, meet Josh Weintraub.

Company Role: Head of Insurance Technology

Most likely to: See the risks

Secret talent: Can juggle

This third-generation New Yorker has always set his sights on ways he could help people, even with his childhood dream of becoming a doctor. And while his medical aspirations never came into fruition, he’s been advising customers as an expert in the life insurance technology industry since 2003. With an extensive background in many facets of the policy playground, this Fellow of the Society of Actuaries has a deep knowledge and understanding of how life insurance works. He has been a part of our team since January 2021 and has been reveling in the excitement ever since.

Let’s get to know a little more about Josh.

What do you do, and what does your typical workday look like?
I do many things at String and Key, including designing and pricing new products, managing our underwriting technology team, and interfacing with external parties. I also identify future risks and consistently look at ways to leverage new technologies. So this is all to say that like with most jobs, there is no typical work day.

We organize two-week segments into what we call episodes, and each day, I work to move the ball forward with the tasks due during that time. At the moment, this involves collaborating with our outside vendors, meetings with our consulting support, and hammering out spreadsheets to understand the financial implications of our product development.

What’s your favorite part about working at String and Key?
I love the energy and the blue-sky approach. I love that we get to create this new thing in an environment where creativity and execution are in our DNA.

What excites you about your job?
The constant, fresh challenges of my role. I’ve done and learned more in the past nine months than I would have in years at a large incumbent.

What do you find most challenging about your role?
New challenges are a double-edged sword because they are both exciting and complicated. The ‘newness’ in itself is the challenge because much of what we do in our internal playbook hasn’t yet been developed. We work closely with our partners to develop these processes and playbooks, but it definitely takes a keen focus to stay on top of all the moving pieces.

What are the values that drive you?
I’m driven to create within constraints. Like a sonata or a haiku, the industry has rules, but it also has flexibility. My drive is to innovate within the system and create something that brings value to our customers and enhances their experience of buying and owning our product. At the end of the day, if I can give people the confidence of financial protection, an experience that feels accessible to them, and do this at a cost that works for them and us, I’m a happy person.

How do you stay on top of your game?
I read, I listen, and I drink beers. Seriously. My colleagues in the industry are an invaluable resource — they create articles, do research, and make presentations, so there’s a lot of information circulating within the team. Whether it’s at a conference or a happy hour, I’m always happy to learn from them.

What drew you to tech and what excites you about the industry?
As someone with a background working at large, established insurance companies, tech is a big change for me. But the draw is obvious: we get to push the needle a little bit faster and a little bit farther. Everyone agrees the customer experience has room to improve, and, at the moment, tech is the best way to achieve that.

What’s one thing — either industry-related or not — that you’ve learned in the last month?
The opening notes for Blue Train on the trumpet are not all that hard. I’m still terrible at it, but I can see a beginner like me making a reasonable go of it with some consistent practice.

If you could swap places with anyone at String and Key, who would it be and why?
I would swap places with Robin Martucci-Livote, our Chief of Underwriting Technology. Robin has so many great things going on. She lives in the Hudson Valley region (which is just gorgeous), she always has a smile and pep in her voice, and she knows underwriting technology from top-to-bottom. But, more than that, she knows how to take that specialized knowledge and merge it with emerging technology to create better customer experiences while watching our bottom line.

What unexpected subject could you give a one-hour presentation on with no advance prep?
One hour is a long time, but I could probably teach a workshop on making salmon teriyaki or designing furniture with CAD software. I recently replaced my bathroom sink and had a very specific vision of what I wanted. I ended up designing it myself, finding a fabricator to build it, and sourcing various parts and materials for finishings. It was a labor of love, meaning the labor was really long and now I love it.

What keeps you busy outside of work?
In the summer, I canoe with a club on the Hudson River. We have four outrigger canoes that seat six people each. It’s great to be on the water on a hot day. Also, my quarantine hobby was learning to play the trumpet (see my comment about Blue Train). I’m fairly terrible at it, and you should not let me play for you, but I love it.

Can you list five hashtags that describe your personality?

#Curious #Social #SecretCatPerson #MusicJunkie #PlantLover

Lighting Round:

Vacation or staycation?
Vacation.

Netflix or Hulu?
Netflix.

Night or morning?
Morning.

Rich and famous or rich and unknown?
Rich and unknown.

Art museum or history museum?
Art.

Interested in working at String and Key? Join us!