How AI is reshaping underwriting into a career of the future

The insurance industry’s traditionally old-school approach to technology isn’t helping. The new generations of workers are digital natives, some even AI-native, and their expectations for the technology they use in their personal and professional lives are high, and their tolerance for inefficiency is low.

In this post, we’ll dig into why legacy systems and processes deter new talent and cause burnout in existing underwriters, how agentic AI is bringing insurance and underwriting into the 21st century, and what insurers can do to rebrand the underwriting role to attract a new generation of AI-ready workers.

The problem with traditional underwriting technology

The next generation of workers isn’t showing interest in insurance careers. And if you look at the tools and processes many insurers use, it’s not hard to see why. They encounter fragmented data, multiple point solutions requiring constant task switching, manual processing, and interfaces that have barely changed since the 1990s—before some of these workers were born. None of that indicates the fast-paced, innovative ethos of current society, and even discourages current underwriters from continuing in the profession.

That puts insurers in a tight spot when trying to attract new talent. The next generation brings a lot to the table, but many aren't even aware of underwriting as a career path. When they do learn about it, the perception that the insurance industry is stuck in legacy systems, with no long-term career progression, keeps them from considering it seriously. While better outreach to schools and universities could help address the awareness gap, insurers must also make the career attractive once students discover it; technology improvements alone won't solve the talent shortage.

This talent crisis poses real challenges, but some insurers are finding a way forward. While the insurance industry has been slow to evolve with advances in technology and user experience, innovative organizations are leading the transformation and adopting new tools and technology, like agentic AI, that are already transforming insurance and the underwriting discipline.

Can agentic AI make underwriting cool?

While it may seem like AI is attached to just about everything these days, some industries are seeing significant transformations as a result of developments in AI-assisted solutions, and insurance is at the top of that list.

Decades of struggling with piecemeal solutions patched together that often don’t achieve the intended result have left underwriters burnt out and potential workers turned off. And this is where agentic AI in insurance has the potential to get underwriting back on the list of hot careers.

While the insurance industry has been slow to adopt new tech and ways of thinking, it's at the precipice of major change, and the next generation of workers is poised to usher in a new era of underwriting.

Here’s what agentic AI offers to the next generation of workers that insurers need to highlight to attract top talent, and ensure skilled underwriters can effectively pass down their industry expertise.

Cutting-edge skills exposure

AI isn't going anywhere, which means current and future generations of workers need to be fluent in AI tools and best practices. Insurers that can offer tools and solutions that leverage agentic AI as part of the underwriting process give workers hands-on experience that accelerates their career growth and opens doors across industries.

Elevates the underwriter’s role

A major benefit of AI in insurance is the automation of manual, repetitive tasks that can make underwriting feel like an administrative role rather than the strategic role it’s intended to be. With AI, data entry tasks, submission triage, document review, data collection, rating, pricing, quoting, and more can be automated. This frees up underwriters to focus on higher-level responsibilities like developing broker relationships and assessing complex risks. 

Enables effective knowledge transfer

In addition to appealing to a tech-savvy generation, AI also frees up veteran underwriters to focus on training new underwriters on the more complex and nuanced aspects of the role—all the things AI can’t assist with. 

With legacy underwriting tools, it can take years before an underwriter is trusted to handle complex risks. With AI-guided decision support, that learning curve compresses dramatically. New underwriters gain confidence faster, managers spend less time handholding, and the team can absorb turnover without losing momentum.

Democratizes access to insights

In many organizations, the best knowledge is siloed with a handful of experts. Agentic AI surfaces those insights broadly so every new hire, not just those lucky enough to be mentored by a star underwriter, benefits from consistent, high-quality guidance.

Agentic AI can show the reasoning path for every underwriting action, highlighting which data points, risk attributes, or portfolio considerations drove a recommendation. New underwriters can now see beyond the “yes” or “no,” and understand why.

Agentic AI doesn’t just follow static rules. It continuously learns from underwriter behavior, historical submissions, and portfolio outcomes to refine its guidance. For example:

• Pattern recognition from history: By analyzing years of submission and claims data, the AI surfaces correlations that might not be obvious, like how a certain class of business performs differently across geographies or economic cycles.
• Learning from expert actions: Every decision an experienced underwriter makes,  whether to quote, decline, or negotiate, teaches the system. Over time, the AI adapts its recommendations to reflect the nuanced judgment patterns of the best underwriters.
• Dynamic feedback loops: As market conditions change or a carrier’s appetite shifts, the AI recalibrates, ensuring that new underwriters are guided by living, evolving knowledge.

Rebranding underwriting as a career of the future

If insurers want to solve the looming talent crisis, they need to reshape the perception of underwriting itself. That means repositioning the role as a modern, tech-enabled career path that aligns with the ambitions and expectations of today’s workforce. Here are some tips to bring the benefits of agentic AI in underwriting into the spotlight and attract the next generation.

1. Highlight technology-forward career paths

Position underwriting as a role at the intersection of technology, data science, and strategic decision-making. Use job descriptions, career pages, and recruitment campaigns to showcase how underwriters now work with AI, predictive analytics, and portfolio optimization tools, not just spreadsheets and emails.

2. Invest in early-career education and outreach

Partner with universities, coding bootcamps, and data science programs to introduce underwriting as a career option early on. Emphasize the blend of domain expertise, human judgment, and AI fluency that defines the future of underwriting.

3. Showcase meaningful impact

Younger generations want to make an impact. Insurers should promote underwriting as a role that directly influences business outcomes and supports resilience in communities, from climate adaptation to cyber risk protection. It’s not just risk selection; it’s shaping the future of societal stability.

4. Elevate internal career branding

Internally, give underwriting teams the spotlight. Use internal communications to celebrate underwriter wins, share stories of how AI tools enhance strategic thinking, and promote career development opportunities that reflect a future-facing role.

Underwriting reimagined with agentic AI

Agentic AI offers insurers a once-in-a-generation opportunity to reimagine the underwriting role as strategic, high-impact, and future-focused. By eliminating the manual processes, surfacing real-time insights, and accelerating the path to expertise, agentic AI makes underwriting more efficient and more attractive to the next generation of workers.