It’s been a wild couple of years for the insurance industry. Companies are charging full steam ahead on their AI initiatives; M&A across the distribution space continues to consolidate the industry; premiums (along with risk) are on the rise; a full-fledged talent exodus is fully underway; and trust in institutions (including insurance companies) is at an all-time low.
All of which got us wondering: what’s it like to work in insurance right now? And, more specifically, what’s it like to be working on the customer side of things–both directly and indirectly?
That’s the question our latest research study, which is currently underway, is seeking to answer.
We’ve been talking to claims specialists, agents and brokers, underwriters, and others on the frontlines of insurance and are beginning to turn up some interesting stories and starting to see themes emerge–around AI, technology transformation, workforce trends, and, most interesting to us (as UX designers), what it’s like to work with customers.
Here are a few of our early insights:
1. Customers are unhappier than ever — and it’s making the job harder and even ruining it for some
“So my entire career, I have loved it. Like, I could not have found a better fit. And the tasks that I do for the job itself, I still enjoy very much. The working with the public part though—that is starting to kind of ruin it for me, honestly.
Melissa, Commercial Account Executive, 17 years in the industry
Melissa described a conspicuous shift in customer relationships over the last several years, one she traces back to Covid. For most of her career, relationships with customers were the most rewarding part of her job. She prided herself on them, and customers often followed her as she moved between agencies. Now, she says, those same interactions are ruining the job for her: “95% of my interactions with customers are negative.”
She connects the change to a number of factors. Brands like Amazon have reshaped expectations around speed and convenience, creating demands that can be difficult to meet in insurance. At the same time, the small business owners she serves are under increasing economic pressure. With prices rising everywhere, insurance can feel like one more place they’re being nickel-and-dimed.
She also pointed to examples of carriers alienating customers and disregarding their experience as they muddle through failed attempts at technology transformation. These experiences only reinforce an already poor perception of the industry, which she believes has worsened in recent years.
Melissa is not alone. As one claims specialist we spoke with noted in reference to commercials she’s seen for attorneys who will work with customers to sue their insurance companies, “they are making it seem like we are the bad guys. So of course regular people are hearing that, they’re going to just automatically run with that.”
And while customers may be impatient with insurance companies and have unrealistic expectations, the sentiment doesn’t come out of nowhere. As one underwriter put it, “In our industry, we don’t talk about the customer’s best interests. I just don’t see that. To be honest, it just comes down to the dollar.”
2. Technology is getting better, but the industry is still behind
"10, 15 years ago, we had manual files in a file room. Anytime you wanted to look at an account, you had to get up, go pull the file, flip through papers to figure out the answer. Whereas now it's in one system and I just click, OK."
Rayna, Commercial Underwriter, 20+ years in the industry
While it is undeniable that insurance industry looks markedly different than it did 10-20 years ago, in large part thanks to technology, that doesn’t mean the industry has fully caught up. Unsurprisingly, we heard alot about disconnected systems, clunky, finicky software, and a patchwork of manual processes.
“We have this CRM over here, and then our policy management over here, and then our claims stuff is over here, and then our quoting stuff is over here. It’s all scattered in different spots… I feel like it would be much easier if everything was a little more compact.”
One agent blamed the state of tech at her agency on the pace of growth at her agency, which is rapidly acquiring ne agencies. With so many new agencies coming on board, all with their own technology and processes, it’s hard to move everyone onto he same systems, and the inefficiencies persist, limiting what kinds of technology are made available to agents to support them in more effectively doing their jobs.
This has downstream effects on the customer: slowing down everything from quoting to claims processing, and in some instances leaving insurance workers feeling out of sync with customer expectations. As one woman we spoke with explained:
“People will be like, can you text me? And I’m like, I can’t unfortunately, because I’m using a landline connected to my laptop.”
3. AI is helpful, but people are wary, and its impact is uneven
"I like AI for me, you know, but at a higher level there are obviously things— the big scope, the implications, and all of that — to be worried about. But using it is very helpful."
Haley, Crop Insurance Underwriter, 4 years in the industry
We heard some version of this from almost everyone we spoke with who is using AI in their work. Most of our research participants have found that AI is making them more efficient and effective at their jobs, but are concerned about its implications in the long run— everything from job loss to the concern that AI will be used to do things that they believe should remain in the hands of people.
As an agent told us, “I’d be concerned if underwriting became automated because it can be so nuanced. I’d worry that AI would make decisions based on keywords, without giving you an opportunity to explain the situation or provide context that might change the decision. I think that could really hurt customers and make my job harder.”
Despite concerns like this, most people we spoke with find AI valuable–when they are able to use it. Several people we spoke to told us they had no access to AI and/or that many of the most useful tools were disabled.
“There are certain built-in AI features in a lot of the programs we use that are not enabled… Teams has a bunch of additional apps you can add on that are AI, so they’ll automatically transcribe calls and whatever. And those are disabled, and we have to submit for admin approval to get them, and I’ve never received a response to any of the admin approval.”
“They block AI on our laptops. I tried to use ChatGPT one day because I wanted to put together a little summary of something and I wanted some assistance, and I couldn’t do it… I feel like we’re kind of old school.”
So while insurance workers are finding value in using AI, this value is not evenly distributed across the industry, with some still lacking basic access.
4. The workforce is being squeezed on both sides
“There’s not a lot of youth, or people from other generations, coming up or really wanting to get into claims. I think, to put it quite simply, claims aren’t sexy.”
Nadia, Property Claims Manager, 10 years in the industry
Across the industry, this sentiment is shared. Experienced employees are approaching retirement, taking decades of specialized knowledge with them, while the people who might replace them aren’t necessarily lining up to do so.
One participant described watching this happen firsthand with her father: “They call him ‘the Hail guy.’ He’s very well known, and he’s planning on retiring in the next two or three years. I’m like, hmm, there’s really nobody up for that position.”
And the problem isn’t simply attracting people into Insurance. According to our research participants, companies are also struggling to keep new entrants there long enough to develop the expertise the industry is losing. Several participants described a trend of new employees coming into the job and quickly leaving.
As one participant put it, “It seems like nowadays people are just kind of, ‘Yeah, well, I’ll try it out. It’s a job, and it looks like they like the pay.’” At her previous employer, she estimated that 90% of new hires left within their first 30 days, either of their own accord or because they weren’t meeting expectations.
That leaves the industry squeezed on both sides. As retirees with highly specific expertise leave the industry behind, new entrants aren’t sticking around long enough to build up their own expertise. This puts more pressure on the people who remain, who are left to absorb additional work, fill knowledge gaps, and bring newer employees up to speed, often while trying to keep up with their own responsibilities.
For all its challenges, insurance is still a career people stick with
For all the challenges the people we spoke with described, many also talked about insurance as a remarkably stable career, particularly once people find their way into it and stick around.
As Nadia, a property claims mnager put it, “I think it is an economy-proof job. I feel like insurance is something that’s just always going to be there. So I feel like no matter what’s going on in the world, I think this is one of those jobs that, for the most part, is very secure.”
Lauren, who works in claims, was even more matter-of-fact: “I don’t think people will unfortunately ever stop getting injured, so it’s good job security.”
That raises an important question: If insurance offers the kind of stability that keeps people in the industry for decades, why is it so difficult to get the next generation through the door?
One answer we heard is surprisingly simple: a lot of people don’t know these careers exist.
“I think a lot of Gen Zers don’t know about insurance,” Rayna told us. She described young people being introduced to the field almost by accident, often through a counselor or advisor suggesting risk management when they aren’t sure what they want to do. “They’re like, ‘Oh, I never heard of that.’”
But she has also seen what happens when insurance companies actively introduce young people to the industry. Her company recruits on college campuses and brings in a new group of interns each year. According to Rayna, “99% of the time they get hired.”
It’s a small but important counterpoint to the workforce challenges we heard throughout these conversations. Insurance may struggle to get people through the front door, but once people understand the work, find their place in it, and make it through those early years, many build careers that last decades.
And perhaps that’s one of the tensions emerging from this research. The people we spoke with aren’t describing an industry or careers they necessarily want to leave. What we’re hearing is that they still value and even enjoy the work, but it’s being made harder by frustrated customers, outdated technology, uneven access to new tools, and a workforce stretched increasingly thin.
As our research continues, this tension is something we want to understand better: not just what’s changing about insurance work, but what it will take to make the work itself better for the people doing it.
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Help us understand what it’s like to work in insurance right now.
Our research is still underway, and we want to hear from underwriters, agents, brokers, claims adjusters, customer service representatives, and anyone whose role involves supporting customers, directly or indirectly about what it’s like to work in insurance. Take our 10-minute survey. The first 50 people who complete it will receive a $20 Visa gift card. The survey closes October 5, 2026.
Survey
We are conducting research to better understand what it’s like to work in insurance today—and how the industry is changing. We’re interested in your perspective on the tools and technology you use, AI, career and workforce trends, customer experience, and the future of the industry.
