Category: Group Benefits

Voluntary Benefits: How Offering More Options Can Set Your Business Apart
July 13, 2026
In today's competitive job market, attracting and keeping talented employees often comes down to more than salary. Benefits packages play a major role in how...

Understanding Disability Insurance as Part of Your Employee Benefits Package
June 28, 2026
When employers build group benefits packages, the conversation often centers on health insurance. But one category of coverage that deserves more attention is disability insurance....

Why Offering Group Benefits Can Help Your Business Attract and Retain Employees
June 13, 2026
In today's competitive job market, salary alone is rarely enough to attract and keep talented employees. Group benefits — including health insurance, dental and vision...

Talking Through Open Enrollment with Generation Z
May 28, 2026
Open enrollment can be confusing for any employee, but Generation Z workers may be dealing with these choices for the first time. Many are new...

The Impact of AI on HR & Employee Benefits
May 22, 2026
Artificial intelligence has become a key driver of business performance, changing how businesses manage group benefits and human resources. Employers employ these tools to serve...

Group Benefits That Support A Millennial Workforce
April 28, 2026
As the largest generation in the current professional landscape, millennials bring a unique set of priorities to the modern office environment. This demographic values flexibility,...

Top 5 Group Benefits Driving Employee Retention In 2026
April 13, 2026
The professional ecosystem in 2026 has experienced a remarkable transformation, making it necessary for business owners to give priority to their retention strategies to stay...

What Happens if I Use HSA Funds for Non-Qualified Expenses?
March 28, 2026
Health Savings Accounts provide tax advantages for individuals in high-deductible health plans. Following specific rules is essential for maintaining these benefits. Accounts allow for tax-free...

Beyond the Workplace: Extending Group Benefits to Families
March 13, 2026
Many companies find that offering family coverage drives employee retention. It reduces costs from frequent turnover. Employees stay loyal when employer-sponsored plans protect their spouses...

Why Group Health Insurance Is Important for Small Businesses
February 28, 2026
Small businesses compete with larger employers that can offer bigger salaries and broader benefits. Group health insurance helps close that gap by supporting stability in...
Get A Quote
Customer Reviews
Definitely worth an exploratory call - I'm glad I made it.
Brian G
BG
Upside Insurance is my go to insurance group for my business owner clients.
Nolan
N
We will be clients for life.
J Szmanda
JS
Over the past four years, they have consistently demonstrated their expertise
Danielle H
DH
Upside Insurance is Awesome to work with!
Keith B
KB
Our family have worked with the Upside Insurance team for years
Noah W
NW
professional, kind, and focused on doing what’s best for their clients.
S White
SW
If I ever switch companies, I’ll be calling UPSIDE first!
Far S builders
FS
always finding best options and pricing for my business insurances needs
Eric L
EL
They are always quick to help, responsive, and happy to answer any questions
H AZ
HA
