The insurance industry is in the middle of a transformation. Catastrophe frequency and severity continue to rise, underwriting scrutiny is tightening, and artificial intelligence tools are being added to workflows at a rapid pace. At the same time, roughly 400,000 insurance professionals are nearing retirement or expected to leave the industry in 2026.
These major changes have been widely talked about for years now, but what is less discussed is the quiet, but significant, workload changes for new and remaining underwriters.
In the past, an underwriter typically focused on a single line of business within an insurance portfolio. Today, it is often expected that they handle business across many of a carrier's specialties such as umbrella, inland marine, commercial auto, and more. They are expected to write risks in many regions while also navigating unique state regulations, company-specific exclusions, and a growing number of technology systems and data that support underwriting decisions.
They are not just the chef in the kitchen anymore. They are also the server, the supplier, and the waiter. They must understand the full business, from production and compliance to systems usage and stakeholder coordination.
For learning and development (L&D) teams, this shift should be a wake-up call. If underwriting has entered a new era of expectations, then training must follow.
What types of training are needed?
Training should be seen as an evolving target. The pace of innovation gains momentum every year, and that is also true of the systems underwriters rely on to manage their dense workload. Training must reflect the speed of many overlapping changes while being respectful of underwriters dwindling time.
Live in-person training still has value, but it must be intentional and limited. L&D teams should block out a two-week period every year where each underwriter receives two or three coaching sessions in this timeframe focused on new technology updates and organizational changes. These sessions can be a few hours each and blend structured learning with real production work. When underwriters can apply new knowledge immediately within their actual workflow, retention increases and resistance decreases.
Beyond that, the bulk of training should move toward just-in-time learning. The days of the 63-page manual are over since updates happen continuously throughout the year. Recorded video is a particularly useful medium for this approach. It can be used to prepare employees before live in-person training sessions, to develop supplemental training materials throughout the year, and to create FAQs broken down by product line. It can also support quick reference guides that explain the interdependencies of new software functions. Underwriters do not have the luxury of sitting through a lengthy walk-through. By delivering training and updates through digestible, bite-sized video segments, underwriters can consume them on their own schedule. These short modules can also be revisited later when questions arise, which is great for a profession that demands such a large cognitive load.
Insurance companies should also be thoughtful about format. Live sessions sound like a nice, engaging option, but in practice, they are not always effective for underwriter training. This is especially true for training on how to use core systems software. Test environments can be slow to load or unstable, and technical glitches distract from learning objectives. Valuable time is spent troubleshooting problems instead of teaching. For complex systems training, asynchronous recorded demonstrations paired with guided practice tend to produce better outcomes.
Creating training content is no longer reserved for large teams and doesn't require elaborate productions. If a carrier doesn't provide staff with paid video creation tools, there are accessible options such as Camtasia online that can meet the need. The barrier to entry for video creation is lower than ever.
Culture: The biggest obstacle to effective training
Most insurers can build modernized training content, but it's harder to build the culture that allows that content to stick and provide meaningful value. Organizations that embrace strong organizational change management (OCM) create the ideal environment for learning to flourish. That's because OCM is key to breaking down silos and isolated mindsets that get in the way of training.
Within insurance companies, there is often a natural siloing of departments. An example of how this is detrimental comes up in training for shared insurance systems. Everyone uses the same systems but they have vastly different priorities and perspectives about how those systems are used. Information technology teams build or modify the systems, field business teams and underwriters use different functionalities within them, and leadership committees approve budgets and timelines.
Getting each group to work together and understand each other's perspectives and what works best is challenging. Underwriting systems are inherently collaborative because they are part of a much larger, complex sales funnel. If the OCM process does not include meaningful cross-functional input, then critical workflow considerations will often be missed. The team developing a new software enhancement or coverage adjustment may overlook small but essential steps that underwriters rely on every day. Those missed details can compound quickly and lead to drops in productivity with each new update.
Training teams have a responsibility to help because of their unique vantage point. They see where confusion arises, hear feedback from all different employee types, and understand how systems actually function in the day-to-day across departments. When L&D teams are included early in change conversations, they can shape how training is delivered and how change is experienced.
The next era of underwriting professionals requires a broader knowledge base, quicker adaptability, and greater technological fluency than any generation before them. It is up to training professionals to meet them where they are and provide lasting support.
Sara Schiebner is an underwriting communications and training specialist with more than 20 years of experience in the insurance industry. Her work blends communication strategy, content development, and change management with professional designations that include AIT, AINS, AIM, and certification as a Prosci® Change Practitioner. She also serves as a Director at Large on the 2026 Board of Directors for the Association of Change Management Professionals® (ACMP®) Michigan Chapter. Sara specializes in making complex processes feel simple, partnering with teams to navigate technology change with clarity, confidence, and well‑crafted learning experiences.
All views expressed here are the author's own and should not be interpreted as representing the views or positions of any organization with which the author is affiliated. This article is published with permission from the author and may not be reproduced.
(Featured image credit: Adobe Stock)
© Touchpoint Markets, All Rights Reserved. Request academic re-use from www.copyright.com. All other uses, submit a request to TMSalesOperations@arc-network.com. For more information visit Asset & Logo Licensing.