Open enrollment isn’t anyone’s favorite time of year — but the choices you make during this short window can save (or cost) you thousands. In this episode, benefits expert Amy Evans reveals the hidden perks, smarter strategies, and grown-ass moves every woman should know to make the most of her benefits and reduce financial stress.

You’ll learn:

  • Why your benefits package might be worth tens of thousands of dollars — and how to factor that into your total compensation.

  • When and how to ask about benefits during a job search (without sounding awkward).

  • Hidden perks like Employee Assistance Programs (EAP), legal services, and identity theft protection — many of which are free.

  • Why dental insurance isn’t always worth it (and what to do instead).

  • How health advocacy and telehealth can save you time, stress, and money.

  • Why registering for your benefit portals and apps now will save you major headaches later.

About Our Guest

Amy Evans has been simplifying employee benefits for employers and their employees for more than 20 years. As a Client Advisor with Acrisure, Amy provides employers with strategic guidance on employee benefits, business insurance and risk management and helps them navigate complex challenges with confidence. A respected speaker, writer, and podcast guest, Amy is known for her thought leadership on health insurance, sales strategies, and networking with intention. Her active presence on professional social media platforms showcases her commitment to fostering meaningful conversations and delivering actionable insights.

Connect with Amy on LinkedIn.

 

Download the Guide!

Grab the FREE Grown-Ass Woman’s Guide to Open Enrollment
A quick, printable checklist to help you:

  • Know what to look for in your plan options

  • Spot hidden perks that can save you thousands

  • Stay organized before, during, and after enrollment

👉 Download HERE

 

Full Transcript

Jackie: Open enrollment doesn’t exactly make anyone’s top 10 list of exciting life events, but the decisions we make during this short window can have a major impact on our finances, our health, and definitely our peace of mind. If you’ve ever stared at an HR email or benefits portal thinking, I will deal with that later, I’ll deal with that later—then this episode is for you. And if you’re someone who’s self-employed or runs a business where you provide benefits, there’s something in here for you too.

This is The Grown-Ass Woman’s Guide. I’m Jackie MacDougall. Amy Evans has spent more than two decades helping people understand and actually use their benefits. Today, she helps us uncover the hidden perks that can save us thousands and the simple things we can do to make open enrollment a little less painful and a lot more profitable.

A recent AARP survey of people age 50 and older revealed that 24% of older workers are planning to make a job change. But when seeking new employment, salary isn’t the only thing we should consider.

Jackie: When someone is looking for a job, or maybe they’re an employee, how important are the benefits to the overall salary? We’re always looking at how much money I make, but not really necessarily the benefits. How important are they?

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