You're at a crossroads.

We know the way.

Whether you're approaching retirement, navigating a disability, a veteran, or managing benefits for your team — Senior Street Advisory provides honest, clear guidance. Find your situation below.

Who We Serve

Business Owners & HR Managers

Benefits decisions affect your bottom line and your team's wellbeing. The rules are complex, they change frequently, and the cost of getting them wrong falls on you.

Sound familiar?

"One of my longest employees just turned 65. I thought they were covered under our group plan. My accountant told me that since we have fewer than 20 employees, Medicare should have been their primary coverage — and we may have been billing payroll deductions incorrectly."

What you're actually dealing with

The age-65 Medicare primary rule
For businesses with fewer than 20 employees, Medicare becomes the primary payer the moment an employee turns 65 — whether they enroll or not. Continuing to bill group plan premiums without coordinating Medicare is a compliance exposure most small employers don't know about.
No clear process for guiding employees through Medicare enrollment
When employees approach 65, most HR managers have no playbook for guiding them through Medicare enrollment alongside group coverage. The result: confused employees, delayed enrollments, and preventable penalties.
Owner coverage gaps
As a business owner, your individual health insurance options are more expensive and less subsidized than a W-2 employee's — and planning ahead is critical to managing premium costs effectively.

How SSA Guides You

Benefits compliance review
We review your current group plan setup and flag any age-65 Medicare coordination issues before they become a liability.
Employee Medicare transition support
We build a simple "Age 65 Playbook" your HR team can use to guide employees through enrollment at the right time, every time.
Owner coverage planning
We review your personal health and life insurance options as a business owner, including key person coverage.
Ongoing advisory relationship
As your team grows and ages, we're available to review benefit decisions and keep you on track.

Not sure which category fits you?

That's exactly what we're here for. Tell us your situation and we'll help you figure out where you stand — and what to do next. No obligation, no pressure.