With platforms like Glassdoor and Reddit making it easier than ever for job seekers to voice their frustrations, direct criticisms about outdated hiring practices and a lack of transparency are becoming harder to ignore, especially in the insurance industry. One anonymous job seeker summed it up bluntly: “I am going on month 4 of unemployment. I am so mentally drained. I do not know what I am doing wrong to NEVER get selected.”
And yet, these flagrant complaints are emerging at the exact moment the industry can least afford to tune them out.
Across the United States, insurance companies are confronting a significant workforce transition. As seasoned professionals approach retirement, the industry faces the dual challenge of replacing institutional knowledge and attracting new talent to fill critical roles.
Approximately half of the US insurance workforce is expected to retire by 2038, according to the US Bureau of Labor Statistics, opening the door to over 400,000 vacancies in a field that relies heavily on institutional expertise. The numbers are stark: more than one-quarter of insurance professionals today are over the age of 55, while less than 25% of the industry is under the age of 35.
But it's not just a matter of replacing warm bodies. The new talent needed – underwriters, data analysts, risk managers – must be as digitally fluent as they are technically trained. As insurers adopt AI, predictive modeling, and automation tools to stay competitive, the bar for new hires has risen.
At the same time, younger generations remain unconvinced that insurance is where they want to build their careers. Over 50% of Gen Z and Millennial workers hold a negative or neutral perception of the insurance industry. Many cite limited visibility into career pathways, lack of innovation, and outdated technology as key deterrents. Even among those already working in insurance, less than half say they plan to stay long-term.
Underwriting departments have become ground zero for the staffing crunch. With the role shifting rapidly to accommodate more data-driven decision-making, carriers are reporting longer delays in policy approvals, increased internal disruption, and dwindling application rates. According to a 2024 survey by Davies, 63% of senior managers in the insurance industry believe a lack of digital skills is an issue in their workforce, with 30% describing it as “a very serious issue.”
To stem the tide, some insurers are launching aggressive reskilling programs and partnering with universities to modernize their talent pipelines. Others are rebranding entry-level roles with clearer mobility tracks and more attractive pay packages. A growing number of companies are experimenting with remote-first or hybrid arrangements to better appeal to Gen Z, who increasingly prioritize flexibility and meaningful work.
Still, progress is uneven. While larger carriers are accelerating investments in training and tech adoption, many mid-sized and smaller firms remain tethered to legacy systems and slower onboarding cycles. For these companies, the workforce shortage is already affecting performance.
Yet amid these challenges, industry leaders see a rare chance to rethink how talent is sourced, and roles are structured.
“We have succession happening at record speed that we haven’t ever seen over the last 25 years,” said Margaret Resce Milkint, global insurance practice leader. “There is opportunity here to expand our pipeline, to bring in others from other industries... to take advantage of these great roles that are going to be available. New C-suite positions are being developed and reimagined. We have to be very creative in the way we recreate our organizations and elevate them to meet the new challenges the market is putting in front of us.”
Nonetheless, challenges are mounting as climate change, cyberattacks, and shifting regulatory demands force the industry to move faster and smarter. And without a new generation of skilled professionals ready to step in, some worry that insurance – long considered a bedrock of economic resilience – could struggle to keep pace with the risks of the modern world.
In an era where job seekers are more vocal than ever, the question facing insurers isn’t just how to fill the roles left behind, but how to rebuild them in a way that addresses these criticisms and attracts the next generation.
