Showcasing the transition to tech: Sara Callander

Hi Sara, thanks for talking with us today. To start us off, can you walk us through your career?

Sure! I'll start with college. I studied Political Economy at UC Berkeley. After graduating, I moved to NYC and joined a rotational program at the American Insurance Group, or AIG. I didn't do much rotating though, and that was perfectly fine with me! I spent most of my time at AIG as a Business Analyst in the CEO's Office.

Starting off in the C-Suite! How was that?

It was a great place to start. The team was very supportive, and I spent much of my time focusing on high-level strategy, crafting AIG's narrative and conducting analyses. I learned lots very quickly, and overall, the work was interesting and thoughtful.

Why leave AIG then?

It was my first job out of college, and while I enjoyed it, I wanted a few things. First, I wanted to “burn the midnight oil”. There's no substitute for hard work and, especially early in my career, I wanted to be on the steepest learning and working curve. People optimize for work-life balance, but I was looking for an imbalance early-on because I wanted to learn at a faster pace!

Anything else?

Yeah, and this is just as important. I wanted to see the impact of my work. At a firm that is as historic and well-established as AIG, that's difficult to do, even if you're in the CEO's Office.

So what happened next?

Bringing it all together, I decided to look for roles in InsurTech. I was enjoying learning about insurance, and wanted to work at its new frontier. It was important that the next company had some element of social good, and lastly, I wanted to be part of something early-stage. I knew that brought more risk, but I wanted to earn influence and be part of a roller coaster!

You ended up joining Lemonade - how did that come about?

I learned about the company while researching InsurTech options. I loved their commitment to social good and applied for a role. It was not aligned with what I wanted to do or the experience I had, but I figured that the company was new and early enough that if I joined I would be able to create my own path.

How was the recruiting process into Lemonade?

Well, I think my case was pretty unique. I applied online and tried to network, but was not hearing anything back. The company was operating out of a WeWork so one day I just showed up, walked into their office in that WeWork and knocked on the door. I handed them my resume, told them I thought I could help and wanted to interview.

That's part-crazy and full-courageous! Before we get into Lemonade, I'm curious if you ever worried about not being able to come back after transitioning away from AIG?

I think the concern is overblown. I think having some experience in tech actually makes you a more compelling candidate regardless of whether you work at a tech firm or not. Every company needs to be tech-orientated and tech-enabled to succeed in the future!

Tell us about working at Lemonade.

It was the roller coaster I was looking for. My first boss was the Chief Insurance Officer. Early-on, I focused on executing quickly, and I built a reputation for great work output. From there, I got full rein to do whatever was needed to move the company forward.

What were the roles you had?

Like I said, I was able to eventually carve my own path. I spent five years at Lemonade! I think my first role was related to underwriting given my AIG insurance background, but I quickly became a junior product manager. I helped launch our products in multiple states.

That's a big deal for someone in their first role!

Yes, it is! And it goes back to one of the characteristics I was optimizing for - I wanted to see the impact of my work!

As we wrap up, do you have any advice for people who are starting this process?

I think it's important to have a narrative. For me, it was the transition from insurance to InsurTech. Sometimes people cast a very wide net, and that can start to pull you in too many different directions. I think it's better to have an industry or sector. And beyond that, you need to know what you're looking for and be able to articulate that to yourself and the companies you're recruiting for.

Give us your recent best: meal, book and watch.

Meal would be Sol Food in San Rafael, CA, book is The Great Believers by Makkai, and watch is Stranger Things, Season Four!