What if your company’s employee benefits plan could be the secret weapon that keeps your top talent loyal—and even attracts new superstars through the door?

In this enlightening episode of Gen Mess with Tess, host Tess Brigham sits down with powerhouse employee benefits strategist, Sirena Dimas, to pull back the curtain on what really makes benefits matter in today’s rapidly changing workplace.

Key Highlights:

• Why company benefits aren’t just an expense—they’re an underused asset that could drive business growth and retention (and how to shift your mindset).
• Sirena’s unique journey from young mom to industry leader, and the “listening” skill that launched her success.
• The generational evolution of benefits: what companies (and employees!) wanted 20 years ago versus today, including a powerful look at the rise of mental health support and financial wellness benefits.
• Candid stories on multigenerational workplaces and families—like what happens when a Gen X, an elder Millennial, Gen Z, and Alphas all live together (hint: mediation skills come in VERY handy!).
• Practical tips for boosting benefit engagement—open enrollment meetings, digital resources, FAQs, and why communication must match each generation’s style.

Whether you lead a business, manage a team, or just want to understand how work culture is evolving across generations, this episode is packed with the wisdom (and real-world stories) you need to start fixing the Gen Mess—one conversation at a time.

Loved this episode?

• Share it with a manager or HR pro who wants to rethink their benefits strategy!
• Try a new way of communicating with your colleagues this week—see what clarity and connection you can create.
• Stay tuned and subscribe for more insights on navigating generational dynamics at work and at home.

Remember: Your benefits package and your people are your company’s greatest assets. Make sure everyone knows how to use them!

00:00 "Gen Mess Podcast with Tess"

03:27 Insurance: A Personal Journey

07:25 Consumer Mindset: Expense to Asset

11:19 Employee Financial Literacy Gaps

13:47 Navigating Employee Health Benefits

19:54 Children Witness Work Stress

22:39 Graduating in the '90s vs. '00s

25:28 Supportive Client Relationships

29:05 Hands-On Learning Beats Tech

31:20 Printer and Battery Misunderstandings

34:18 Parenting Approaches Across Generations

37:18 "First Speaker Buys the Product"

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