Building a multi-generational approach to insurance coverage

• Key Insight: Learn how generational expectations are forcing insurers to blend digital and human experiences.
• What's at Stake: Employee disengagement could accelerate talent turnover and benefit-plan churn.
• Supporting Data: Satisfaction fell to 61% in late 2025, down from 66%.
• Source: Bullets generated by AI with editorial review

Employees have long since rejected a one-size-fits-all approach to benefits, and it's impacting their interactions with supplemental insurance products, too. 

Different generations have differing expectations around their insurance interactions, with younger employees expecting tech-forward experiences, while older employees are more satisfied with a hand-on approach. Finding the balance is the key to getting employees to engage with these offerings, says Matthew Paul, VP of commercialization at insurance company Heathos.  

"Insurance is a big deal for organizations — it's generally one of the top benefits," Paul says. "Employees often look to that coverage when deciding whether they want to stay at their job or leave, so having coverage that meets all of their needs really matters."

Yet employee satisfaction with their coverage dropped to 61% in late 2025, according to a survey from insurance company WTW, down from 66% the previous year. The decline is driven largely by rising employee expectations and unmet needs, especially as different generations seek vastly different approaches to benefits. While this gap is creating tension, it can be bridged with the right policies and strategies.

Read more: The AI skills gap is turning Gen Z into workplace mentors

"Younger employees expect speed, transparency and ease of interaction," Paul says. "Older, mid-career employees tend to want more hands-on personalization as their needs become more complex." 

Creating a multi-generational strategy

Paul says benefit managers can strike the right balance without sacrificing the ease of technology.  A "digital-first" insurance experience doesn't need to be fully  automated; rather it should feel as intuitive, transparent and responsive as the other platforms employees use every day. Tech can streamline the process of enrolling,  accessing documents, understanding coverage and getting answers quickly and easily — all things older generations benefit from too. 

Additionally, as older generations phase out of the workforce and younger generations like Gen Alpha and Beta break through, continuing to invest in digital landscapes ensures long-term and sustainable success.  

"Continuity and a unified approach is critical at this point," Paul says. "Workplaces are becoming digital-first ecosystems and AI will soon play a big part in the insurance process as well, so continuing to evolve digitally is necessary." 

Read more: Gen Z and millennials surpass older generations on retirement readiness

Customer churn in insurance is often driven less by price and more by experience gaps at key life transitions. When insurers fail to meet policyholders' needs during these moments — whether enrolling, filing a claim, or updating coverage — members are more likely to disengage, highlighting how support and guidance across life stages are critical to retention. 

In fact, according to recent data from insurance software provider Insurity, 28% of Gen Z and 21% of Millennials said they switched insurers after a frustrating experience with an online portal or app, while 26% of Gen Z and 21% of Millennials reported avoiding filing a claim altogether because the digital process was too difficult to navigate. 

No matter the age, creating ease of experience will ensure employees have the tools they need at every life stage, Paul says. 

"Staying flexible is what's important," Paul says. "Organizations who find a way to cater to the full life cycle of their employees no matter their age are the ones that are going to really prosper."