Tailored Benefits: What Employees Want by Generation

Does your employee benefits package resonate with the workers you’re offering it to? Does it offer real value to them at their current life stage? Or does it leave them researching your competitors instead? 

Many employers with a multigenerational and diverse workforce struggle to find the perfect mix of benefits to attract and retain employees. After all, a 21-year-old male entering the workforce is unlikely to be enticed by your generous childcare and retirement planning benefits. While a 64-year-old woman close to retirement may be less invested in their professional development. 

This generational divide makes it nearly impossible for a one-size-fits-all benefits strategy to succeed. In this article, we’ll explore how employee needs vary across generations and how you can tailor your benefits offering to meet employees where they are in life, not just where they sit in your org chart.

The five different generations of the modern workforce

The faces of the modern workforce are incredibly varied, bringing a wide array of experience, skills, and perspectives to the table. Here’s a breakdown of who might feature in your operational line-up: 

• Generation Z: Born between 1997 and 2012, they’re the newest entrants to the workforce, often in entry-level roles or internships. They comprise approximately 18% of the workforce.
• Millennials (or Generation Y): Born between 1981 and 1996, they now make up around 36% of the workforce, often in managerial and tech-savvy roles.
• Generation X: Born between 1965 and 1980, these employees are known for independence and adaptability and currently occupy many mid-to-senior management positions. Gen X makes up around 31% of the workforce. 
• Baby Boomers: Born between 1946 and 1964, some of this generation has now retired, leaving 15% in the workforce. 
• Silent Generation: Born between 1928 and 1945, this generation is almost entirely retired, although around 1% are still working part-time or in advisory roles. They will soon be replaced by Generation Alpha, born between 2010 and 2024. While most of this digital native generation will start working in the late 2020s, some may already be earning while still in education. 

Each generation’s experience of the workplace has been significantly impacted by the economic climate and the cultural norms present as they entered the workforce. Let’s explore how these experiences shape their benefits in practice.

Gen Z: Prioritizing purpose and personalization

Gen Z entered the workforce during one of the most turbulent periods in recent history—the COVID-19 pandemic. Since then, many have navigated a challenging job market punctuated by automation anxiety and being onboarded into remote-first roles with limited access to traditional mentorship or social connection. As the “last in, first out” generation, they’ve felt the fragility of employment early as layoffs have swept across several industries. 

Despite these challenges, the Gen Z age group brings a bold, values-driven energy to the workplace. They care deeply about sustainability, DEIB, and making a meaningful impact, both inside and outside of their job descriptions. Their ideal employee benefits package blends practical support with personal growth: access to alternative mental health therapies, the flexibility to pursue creative side projects, and opportunities to give back through volunteer programs.

Yet, research suggests that the current approach falls short. 63% of Gen Z employees wish their benefits came with more personalized recommendations, and half say the communications they do receive feel irrelevant to them. This is a generation accustomed to curated Spotify playlists and algorithm-fed TikToks, so their expectations for workplace experiences, including benefits, are no different.

To meet Gen Z workers where they are, employers must lean into offering personalized benefits. That could mean offering benefits marketplaces where employees can choose what matters most to them, including therapy stipends, online learning budgets, or paid volunteer days. 

Millennials: Balancing ambition with real-world pressures

Millennials, often positioned as the bridge between digital adopters and digital natives, have matured professionally in a landscape shaped by economic recessions, student loan debt, and skyrocketing housing costs. But while many hold managerial roles, the financial stability once expected of this life stage remains elusive for many.

Not to be held back by the glumness of their situation, Millennials are redefining success on their own terms, opting for side hustles, contract work, or fully remote roles to prioritize flexibility and autonomy. In fact, nearly half of Millennials actively pursue freelance or gig work, according to EY.

They’re also among the most vocal generations when it comes to mental health support. Unlike previous generations, Millennial employees have normalized therapy, self-care, and emotional well-being in the workplace. They’re equally outspoken about their needs when it comes to family forming benefits, whether requesting fertility support, adoption assistance, or flexible childcare options to meet their caring responsibilities.

To meaningfully support Millennials, benefits programs must be more focused on impact. That might include access to financial wellness tools to pay down their student debt, personalized pathways for upskilling, and flexible work arrangements that accommodate parenting, caregiving, or creative entrepreneurship. Crucially, it means offering mental health resources that go beyond basic EAPs, think therapy stipends, coaching, and burnout prevention strategies to support work-life balance. 

Gen X: Managing it all—career, caregiving, and change

Generation X is at the peak of their careers and the center of some of life’s most demanding responsibilities. Many manage large teams at work while also juggling complex personal roles: raising children, supporting college-bound teens, and caring for aging parents. They’re stretched across time, finances, and attention, and the support they need from employers reflects that.

Unlike younger generations just entering the workforce or older ones planning for retirement, Gen X is squarely in the thick of it. They’re making high-stakes decisions for their companies while also navigating high personal costs, especially in caregiving and healthcare where they spend an average of $5,500 per year on healthcare. 

For employers, the takeaway is clear: Gen X needs benefits that help them manage the dual demands of leadership and life. That could include expanded healthcare coverage, dependent care stipends, flexible schedules, and programs designed to support eldercare. They’re also in a key position to benefit from upskilling initiatives, especially as technology reshapes how work gets done.

Baby boomers (and silent generation): Focusing on health, legacy, and financial peace of mind

As Baby Boomers transition into the later stages of their careers, their benefit needs are shifting. Along with the percentage of the Silent Generation still working, these generations share similar priorities: a strong focus on healthcare, financial security, and the ability to support younger family members where needed. 

Baby Boomer employees are naturally less focused on climbing the career ladder and more interested in securing a stable, dignified path toward retirement. And with 10.6% of their spending going toward healthcare, it’s no surprise that medical benefits are at the top of their priority list. 

For employers, this generation presents a valuable opportunity: They bring decades of institutional knowledge, mentorship capacity, and leadership experience. But to retain employees on a part-time or advisory basis, benefits must align with their current lifestyle needs. That could include retirement planning tools, robust healthcare coverage, and support for family caregiving, particularly as many are now helping with grandchildren or aging spouses.

Overcome the challenges of tailoring benefits to different age ranges with Benepass

Designing a benefits package that speaks to every generation might seem like an impossible task, but it doesn’t have to be. Benepass is built for flexibility, empowering employers to offer a single platform that adapts to the needs of each employee, no matter their life stage or priorities.

With Benepass, you can move beyond rigid, prescriptive perks and offer employees the freedom to spend on what matters most to them, whether childcare, fitness, therapy, professional development or even pet care. A modern benefits experience doesn’t ignore traditional needs; it simply makes room for all of them. 

One of the easiest ways to get started is with a Lifestyle Spending Account (LSA). This flexible stipend allows employers to set a budget and define eligible categories, while employees choose how to use it. It’s a simple, scalable way to personalize benefits across your entire workforce, and make every generation feel seen. 

Ready to build a benefits package that works for all? Book a free Benepass demo today or contact sales@getbenepass.com to connect with a benefits specialist.