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My love letter to the Nerds

Lindsay Plotkin

Lindsay Plotkin

Underwriting Lead

September 8, 2022

Awkward introductions

In 2014, I started my career as an underwriter at Chubb, one of the largest insurers in the world. As a post-grad living in SF, I felt like an outlier as an insurance professional working in the tech capital of the world. Nearly all of my non-work friends had jobs in tech and when I met their coworkers I loathed having to explain what I did. I look back at past introductions and cringe. They usually went something like this:

Switching lanes

So it comes as quite the surprise when eight years later, I find myself working in tech. And not just any old tech—insurance tech for the commercial construction industry. Last January I joined Shepherd, an early stage tech startup focused entirely on insurance for contractors. I was drawn to Shepherd by the infectious energy and sheer impressiveness of the team coupled with a desire to take my career to the next level. Surprisingly, the wildest thing about my journey thus far has been obsessing over insurance with none other than my engineering colleagues. If my old self could witness my early exchanges with these coworkers, her jaw would be halfway to the floor.

Most people I’ve encountered who don’t work in insurance immediately assume personal auto or health coverage when I mention my industry. They are surprised to learn that there’s a multi-billion dollar world of commercial lines that impact so much of our day to day lives. When I met my new engineering colleagues I expected they’d know very little about insuring contractors. But on my first day in the office, I was peppered with all kinds of nuanced insurance questions from these teammates. They had already done their homework and wanted me to take them deeper by telling them everything I knew about coverage, pricing, terms, and more. They wanted to hear the war stories: the deals I’d won in the past, and the scars I’d earned over my eight years of underwriting.They were oddly obsessed–it was clear that they had quickly developed a genuine passion for the topic.


A captivated audience

At Shepherd, our engineers have built a proprietary rating platform from the ground up and this system allows us to deliver indications to our broker partners at an unprecedented pace. Ahead of launch, we performed a series of underwriting dry runs using our new platform. How this worked is each member of the insurance team took an unfamiliar risk and ran it through the system from start to finish. The engineers’ primary role in these exercises was to look over our shoulders (literally) and help us work through platform-specific questions while also documenting any bugs or slowdowns. I quickly realized that while I saw the dry run as a chance to understand what the engineers had built, they viewed it as an opportunity to explore the components that fuel our underwriting process. I found myself explaining the anatomy of a deal to a captivated audience. I had to shake myself. I was immediately transported back to my early experiences in San Francisco and couldn’t understand how or why an engineer would be interested in learning about insurance. At the same time, Shepherd would not be successful without this deep engineering engagement. The incredible product they’ve created is an obvious reflection of their passion and drive to improve the industry.

At Shepherd, we are one team.

Today, Shepherd maintains a near-even split between underwriting and engineering—distinguished internally as the ‘writers’ and the ‘nerds.’ You’d imagine there’d be a sharp internal divide between the two functions; however, that couldn’t be any further from our reality. At Shepherd, there is no fence. Our success necessitates continuous cross disciplinary collaboration and this could not be possible if not for the engineers’ curiosity.

I’m extremely grateful to our engineers for building a technology to make me a more efficient underwriter. But what I’m perhaps most indebted to them for, is helping me remember that insurance is cool and worthy of exploration! Most importantly, I’m reminded daily that genuine curiosity is one of the most important elements that comprise a great team.

Thinking back to my own journey into the industry, there was a period of time when I began to second guess my decision to go into insurance. I wasn’t learning or developing at a pace that satisfied me and felt I’d hit a plateau. Joining Shepherd has reaffirmed my career path and ignited a new spark for me professionally. I’ve never worked with a group of individuals as energized and hungry to change the industry for the better. And this contagious energy not only motivates me to show up to work everyday and bring everything I’ve got, but also reminds me of my need for constant growth.


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