A multigenerational workforce requires leaders to understand its diverse needs, life stages, and work environments of employees. At From Day One’s San Francisco conference, leaders shared practical approaches that combine flexibility, technology, and human-centered design to make benefits truly inclusive for everyone.

Inclusive benefits are all about recognizing the diverse needs of its workforce, according to Neela Campbell, VP, head of people at Hims & Hers. “Our biggest challenge right now is looking at our demographic,” she said. “We’re fully remote, with people all over different geographies and different ages and life stages, and we’re constantly designing and redesigning the benefits package and offerings that really can meet people where they’re at.”

That flexibility is essential in a remote-first environment. Campbell says the company quickly learned the importance of being intentional about how it operates. “Zoom fatigue—we’ve all been affected by it,” she said. “What we learned quickly was about really working to be intentional about the way that we are operating as a remote-first company.” 

To help employees thrive, Hims & Hers limits unnecessary meetings, promotes asynchronous work, and emphasizes respect for focus time and personal boundaries. “It might sound simple,” she added, “but when you put it in action, it can be very impactful and valuable.”

Despite being fully remote, the company still values in-person connection. “We have an incredible employee experience team that works really hard to make sure we’re able to meet and have impactful conversations,” Campbell said. Those face-to-face moments help strengthen relationships and foster collaboration, so when employees return home, they maintain that personal connection.

Consider Cognitive Load for All Employees

Supporting employee well-being in the age of AI starts with recognizing just how much mental strain today’s digital world demands—for employees of any age. 

“We are sitting at the intersection of one of the greatest technology transformations of all time,” said Kelly McMahon, VP of organizational effectiveness at Equinix. “When you think about what it takes to actually manage AI workloads and the demand on compute power and space and energy—we serve our customers in enterprise and hyperscaler—and that made me feel a little stressed out.”

Learning new technology can be challenging at times. More than that, though, it’s the constant cognitive switching that comes with it, that affects everyone, she says.

McMahon calculated that she sent and received nearly 20,000 Teams messages so far this year. “When we talk about burnout and cognitive load, that’s what we’re talking about,” she said. “You stop thinking about one thing and you start thinking about another.” The endless pings, meetings, and context changes add up—and for many employees, especially working parents, the load can become unsustainable.

After hitting a wall herself, McMahon said she had to “take a hard look at my calendar and how and where I was spending my time.” Her lesson for other leaders: boundaries are essential. “Start with preservation of the time. Start with your priorities.”

McMahon encourages companies to simplify processes and empower employees to manage their focus. “Simplicity is the ultimate form of sophistication,” she said. “If your calendar is 10 hours back-to-back, you’re probably not going to effectively manage your cognitive load.”

Bridging Generations in the Workplace

At Keysight Technologies, employees span an incredible age range—from their 20s to their 90s. Older employees have key skills that are hard to find and are looking at the end of their career. Younger employees are just starting. Many have different needs, but most have the same core needs.

“It’s about making sure everybody is heard,” said Heather Ostrowski, global senior director of benefits. “We have to design benefits that meet people where they are in life, whether they’re just starting out, raising families, or planning for retirement.”

Convincing leadership to invest in a broad spectrum of well-being programs hasn’t always been easy. “You have to show the value,” Ostrowski said. “Executives want to see data that proves these benefits impact productivity, retention, and health outcomes—and we’ve been able to do that.”

One standout success has been Keysight’s partnership with Sword Health, a virtual physical therapy platform. “We’ve had amazing feedback about the Sword program,” Ostrowski said. “It’s helped reduce musculoskeletal claims—our second-highest cost area—and saved 29 employees from surgery.” The result? Lower healthcare costs and a 14% increase in productivity.

Ostrowski also emphasized the importance of listening and evolving as generational needs shift. “What a 25-year-old values isn’t the same as what a 55-year-old values,” she said. 

Inclusivity is something a company does intentionally, she added. “It has to start small,” Ostrowski said. “You start by creating acceptance, by making it okay to say, ‘I need a mental health day.’ That’s how trust—and real well-being—takes root.”

Simplifying Through Consolidation

As organizations strive to meet the diverse needs of their employees, many are realizing that managing multiple benefit vendors can create unnecessary complexity. “When we think about benefits, oftentimes we’re actually a replacement of other vendors,” said Megan Burns, lead  benefits solutions consultant at Benepass. “What we do from a customizable spending accounts platform is consolidate a budget to one card.”

That one card gives employees freedom and flexibility, something the company values because it matters to people. “We work with employers to put parameters around how employees can choose to use those benefit dollars,” Burns said. “Sometimes it’s physical fitness, sometimes it’s emotional health, and oftentimes it’s things like food delivery or groceries.” By consolidating benefits into a single, intuitive platform, Benepass streamlines administration while it increases engagement, as employees are more likely to use benefits that fit their personal lifestyles.

While consolidation is more convenient for workers, it also saves money, says Burns. “We work with employers to increase their budget by future cost avoidance,” she said, referring to the financial efficiencies that come from merging multiple wellness, fitness, and reimbursement programs into one system.

Blending AI With Human Care

AI has joined the workforce, and it’s not necessarily a bad thing. Ellie Smith, senior clinical specialist at Sword Health, emphasized that technology can enhance, not replace, the personal touch of professional care. “The AI clinician is not making any decisions,” she said. “They’re just there to make the experience more fun, gather feedback, and help the PT provide better care.”

Sword Health’s digital physical therapy program illustrates how AI can complement human expertise. Patients receive real-time feedback on their movements through a tablet-based system, while PTs monitor and adjust treatment plans based on data collected. “Having those pre- and post-session conversations has been really helpful because it gives me even more information to provide better care,” said Smith. 

This integration allows employees to manage musculoskeletal health on their own schedules, easing the cognitive load of traditional in-person appointments while maintaining high-quality guidance.

The combination of AI and human care also supports long-term health outcomes. Smith noted that programs like Sword’s Move initiative help patients build strength alongside other interventions, such as GLP-1 therapy. “By pairing it with a strength-based program, we help individuals stay strong, prevent injury, and build long-term healthy habits,” she said.

Across industries, these hybrid approaches demonstrate a broader principle: technology should simplify and augment human effort rather than overwhelm it. 

The panelists agreed: inclusive well-being isn’t a one-size-fits-all solution. Leaders must focus on a continuous process of listening, adapting, and integrating tools that simplify and enhance employees’ experiences. From consolidating benefits to blending AI with human care, the common thread is flexibility and personalization. By thoughtfully addressing diverse needs, organizations can create a culture where employees feel supported, empowered, and able to thrive—no matter their age, role, or stage of life.

Carrie Snider is a Phoenix-based journalist and marketing copywriter.

(Photos by David Coe for From Day One)