Chelsea Adler discusses what it’s like to work in an insurtech start-up, and how it compares to her experience at a traditional insurance company in terms of culture, work-life balance and opportunities

Intrigued by insurtech? Many start-ups offer exciting perks such as unlimited holiday and free lunch while claiming to revolutionise the archaic insurance industry. But what is it really like to work for these companies? Does it live up to the hype? Initially, I was sceptical.
I started my career at a large and well-established US insurance carrier, and when insurtechs started bursting onto the scene, I was the first to doubt their potential. However, in 2019, I made the leap and joined an insurtech that leverages mobile telematics for private passenger motor insurance.
After five years at a traditional carrier and almost three years at an insurtech, I can honestly say that my experience has been equally positive at each, but different in nearly every way. Both environments provide distinct benefits and challenges, as well as opportunities and limitations. As the options for actuarial employment increase, it can be tough to know which path to pursue without having worked in a variety of settings. I hope that, by sharing my experience, I can provide valuable insight as you navigate your next career move.
Culture
First, let’s talk about culture. There are many ways to define company culture. To start, I’ll focus on the way in which work is done.
When I joined an insurance carrier, I participated in a formal training programme that lasted about three to four months. In addition to my direct supervisor, I was assigned a trainer who provided hands-on guidance to help me learn my job. This person set up time for me to meet the team and company leadership, and provided documentation for all the processes so I could get up to speed on the expectations for my role. Whenever I had questions, he was there to help.
My experience on joining an insurtech was very different. On my first day, I attended one onboarding session and was then shown to my desk, handed a laptop and told to ‘Slack’ if I had any questions.
Then I was left to wonder:
- What do I do now?
- How do I get my computer set up with the applications I’ll need?
- What in the world is Slack? (A workplace messaging service, it turns out.)
This initial experience highlights one of the biggest differences between the start-up and traditional insurance worlds: structure versus autonomy. At an established carrier, there is often a well-defined and documented process for everything. At newer companies, it’s possible that these do not exist yet; every tool and procedure must be built from scratch. Because of this, I was given the opportunity to influence and establish these processes over time. While there are benefits to both approaches, I believe the latter was more effective for my own growth. Although it was a bit daunting, it forced me to think critically about why we do what we do and to come up with creative ways for achieving our objectives.
The next major difference is the pace of work. When I speak with others at traditional insurance companies, the most common complaint I hear is not being able to move quickly enough due to bureaucracy and legacy systems. This means the pace of work tends to be slower and potentially more predictable. On the other hand, insurtechs tend to be high-velocity environments. Decisions are made quickly and technology enables rapid execution and iteration.
In addition, the rate of change is incredible. During the time I’ve been in insurtech, my team hasn’t done the same process twice. As the company grows and we learn more, the data, processes and work are constantly evolving. There’s no precedent to follow, and priorities shift almost daily. Setting realistic timelines and expectations can be one of the most challenging aspects of operating in this space. If you thrive in uncertainty, this environment can be exciting and rewarding. However, for some the dynamic pace can be overwhelming.
At a large corporation, job responsibilities are often clearly defined. Specific roles are established to align business needs with skillsets and to enable efficient completion of work. At a start-up, there tends to be an ‘all hands-on deck’ mentality. Everyone does what it takes to get the job done. Often the work spans multiple disciplines and allows for the opportunity to learn new skills while collaborating with individuals across the organisation.
“You’re more likely to develop a variety of skills and hone them more quickly, which can open doors to new opportunities within and outside of the company”
These dynamics lead to the next difference I’ve observed: siloed versus broad-reaching engagement. In a traditional insurance environment, it’s common to have a very clear set of stakeholders, and collaboration outside of this core group of customers tends to be limited. In contrast, those in insurtech may engage with various individuals or departments across the company, depending on the scope and needs of a particular project. Because the work is constantly evolving, one must consult experts from various functional areas to get the job done.
Work-life balance
Next, let’s shift into work-life balance. I’ll focus on this in terms of pace of work and flexibility. We’ve already covered the first pretty extensively: if you work for a start-up, you will likely be expected to produce results more quickly than you would at a more stable, established firm. When a company is starting off, it’s necessary to try new things, learn, adapt and then iterate quickly.
In light of this, there tends to be more focus on the actual work product and impact as opposed to the way in which the work is done. Especially pre-pandemic, insurtechs were much more informal and relaxed than traditional insurance companies. For example, many corporate campuses had dress codes that required wearing professional attire into the office, whereas when I first joined an insurtech, I was told I could wear anything I was comfortable in – even pyjamas.
Beyond dress, start-ups also tend to be more flexible in terms of when and where people work. Post COVID-19, flexibility has increased for all companies – but it seems that more traditional corporations are requiring some return to the office, while most insurtechs remain entirely remote or allow for employee choice in terms of where one prefers to work. Additionally, there tend to be less formal work hours and more freedom to flex time if needed in an insurtech environment, especially when unlimited holiday policies are provided.
Opportunities
For those interested in climbing the corporate ladder, paths for career progression tend to be more clearly defined at large companies. As an example, many have robust rotation programmes that automatically expose actuaries to a variety of areas at a regular cadence, which can provide constant growth and potential for upward mobility. In addition, the number of positions available at any given level are greater, given the size of the company.
At an insurtech, it may be less obvious what steps to take to move from one position to another. However, you’re more likely to develop a variety of skills and hone them more quickly, which can open doors to new opportunities within and outside of the company. One benefit of the smaller environment is seeing the impact you’ve made more clearly. There are more opportunities to interact with leadership and influence company direction in the insurtech space.
These statements are based on the author’s personal experience and conversations with others working in both traditional insurance and insurtech environments. They do not necessarily reflect every company, nor do they reflect the opinions of her current or previous employers.
Chelsea Adler is a senior pricing manager and actuary at Root Inc.
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