Jobs2Careers logoHome

Insurance+Underwriter

Milwaukee,WI

1555 Insurance+Underwriter jobs in Milwaukee,WI

Featured Opportunity
The Radu Group Logo

The Radu Group - Lisle, IL

Call Center Representative - Life Insurance
~ 1 hr 47 min OnsiteFlexible Schedule
Apply Directly
Insurance Sales - No Sales Experience Required!

PLATINUM SUPPLEMENTAL INSURANCE

Milwaukee, WI

Requires TravelChat NowUrgently Hiring

Our first-year sales consultants typically earn $75,000 or more, with top performers exceeding $100,000.
$75,000+ is typical; $100,000+ is achievable for motivated individuals.
Earn ongoing annual income from policies you've already sold-your book of business grows with you year after year.
Generous bonuses reward your consistency and results.
This is a commission-based position
Annual renewal commissions create a growing income stream from your existing book of business.
We'll train you, license you, and pay you while you learn.
Luxury Travel Incentives: Earn all-expenses-paid trips for you and a guest-quarterly getaways and annual destinations.
We provide online training to help you earn your insurance license before you ever go to the field.
One Week of Paid Training
Paid From Day One in the Field
AI-Powered Coaching: Get personalized feedback, interactive coaching, and real-time support that helps you master our 10-step sales process faster and more confidently than traditional training.
Ongoing Back-Office Support
All-Expenses-Paid Trips: Quarterly getaways and annual vacations for top performers-bring a significant other, on us.
Work Monday through Thursday
No evenings.
No Saturdays.
A Monday-Thursday schedule means three-day weekends, every week.
Overnight travel Monday- Thursday within your assigned territory.
A four-day workweek
No insurance experience required.
You're 18+
Ready for overnight travel Monday- Thursday within your assigned territory.
Easy Apply
Call Center Representative - Life Insurance

Chamberlain Agencies

Brookfield, WI 53045

~ 22 min OnsiteFlexible Schedule

Unlimited Earning Potential: Your dedication determines your earnings*
This is a commission only role with average earnings of $65,000+ in the first year and uncapped room for rapid growth based on performance.
Grow with Us: Dive into continuous learning and development opportunities.
Virtual Company Overview: Once your application is in, you'll receive an invite to a virtual overview, detailing everything you need to know about the position. This session lasts 20-30 minutes, and you can self-schedule at your convenience, often on the same day.
Flexible Scheduling: Enjoy the benefits of a full-time role that has flexible hours.
Full-time role
Ability to obtain a license is required.
Apply Directly
Sales Representative - 4 Day Work Week

PLATINUM SUPPLEMENTAL INSURANCE

Milwaukee, WI

Requires TravelChat NowUrgently Hiring

Our first-year sales consultants typically earn $75,000 or more, with top performers exceeding $100,000.
$75,000+ is typical; $100,000+ is achievable for motivated individuals.
Earn ongoing annual income from policies you've already sold-your book of business grows with you year after year.
Generous bonuses reward your consistency and results.
This is a commission-based position
Annual renewal commissions create a growing income stream from your existing book of business.
We'll train you, license you, and pay you while you learn.
Luxury Travel Incentives: Earn all-expenses-paid trips for you and a guest-quarterly getaways and annual destinations.
We provide online training to help you earn your insurance license before you ever go to the field.
One Week of Paid Training
Paid From Day One in the Field
AI-Powered Coaching: Get personalized feedback, interactive coaching, and real-time support that helps you master our 10-step sales process faster and more confidently than traditional training.
Ongoing Back-Office Support
All-Expenses-Paid Trips: Quarterly getaways and annual vacations for top performers-bring a significant other, on us.
Work Monday through Thursday
No evenings.
No Saturdays.
A Monday-Thursday schedule means three-day weekends, every week.
Overnight travel Monday- Thursday within your assigned territory.
A four-day workweek
No insurance experience required.
You're 18+
Ready for overnight travel Monday- Thursday within your assigned territory.
New, Posted 15 hours ago
Recommended
Easy Apply
Work From Home Insurance Sales

HMG Careers

Milwaukee, WI

RemoteChat NowHealth Insurance

First-year earnings are estimated at $67,000–$70,00, based on individual sales performance.
Commission and bonus compensation
Renewal commissions that can create long-term income
Stock-option opportunities
You will be provided with your leads, training, technology, and ongoing support.
Union membership, protections, and positions.
Leads provided
No traditional cold calling
Medical, dental, and prescription benefits
Comprehensive training and licensing support
We will help you understand the licensing process and identify an appropriate solution.
Flexible hours - not just 8-5.
Have basic computer skills
Are comfortable using Zoom
You must hold or be willing to obtain the life-insurance license required in your province or state.
Applicants must be legally authorized to work in Canada or the United States.
Have sales, customer-service, hospitality, recruiting, or other people-facing experience. This is helpful but not required.
New, Posted 17 hours ago
Apply Directly
Collision Prepper

The Boyd Group

Milwaukee, WI 53244

$18-$22/hr
OnsiteEducation AssistanceHealth InsurancePaid Time OffRetirement Benefit

$18-$22+ per hour based on experience
On-going I-Car and Industry Training Programs,
Professional Development Opportunities.
Annual Paid Time Off (PTO) plans
2 weeks of Paid Parental Leave for Full time Employees who work a minimum of 30 hours per week
6 paid holidays annually
Medical, Prescription Drug, Dental & Vision Insurance effective Day 1
401(k) Retirement Plan with company match
Employer Paid Short-Term Disability & Life Insurance
Additional Voluntary Life Insurance
Continuing Education Opportunities
Free Prescription or Non-Prescription Safety Glasses annually
Annual Voluntary Uniform Stipend
Recommended
Apply Directly
Work From Home Insurance Specialist - Licensed

Foundever

Milwaukee, WI

RemoteHealth InsurancePaid Time OffRetirement Benefit

$19/hr
$19/H
$18/H - $19/H
Opportunities for bonuses
Paid Training
401(k) matching
Health, dental, and vision insurance
Disability insurance
Paid time off
Career growth
Foundever will ship necessary equipment, including a headset.
Weekend shifts as needed
No less than 40 hrs. per week
Must have open availability during operating hours.
A Producer Personal Lines License is required for this position.
Please have your NPN# ready for the application.
Please have your NPN ready
Must be at least 18 years old
High school diploma or GED equivalent required.
Must have open availability during operating hours.
A hardwired high speed internet connection
A quiet, distraction-free space is essential
Webcam video presence will be required during training and production.
Can not be a primary care provider during hours of operation.
Ability to navigate system tools to search for answers & information.
Preferred 6 months - 2 years of relevant work experience
Apply Directly
Residential Youth Caregiver - Relocation to Hershey, PA Required

Milton Hershey School

Wauwatosa, WI 53208

Apply Directly
Residential Youth Caregiver - Relocation to Hershey, PA Required

Milton Hershey School

West Allis, WI 53214

New, Posted 9 hours ago
Apply Directly
Mobile Associate - Retail Sales

T-Mobile

Milwaukee, WI 53217

$20/hr
OnsiteChildcare AssistanceEducation AssistanceHealth InsurancePaid Time OffRetirement Benefit

Hourly Base Pay: $18.00, plus $5.00 per hour training pay.
Eligible for an annualized incentive target of $18,000/year.
All employees at T-Mobile are guaranteed to earn $20/hour inclusive of base pay and incentives.
Annual stock grant
Employee stock purchase plan
401(k)
Access to free, year-round money coaches
On-the-job training
Annual Stock Grant
Medical, dental and vision insurance
A flexible spending account
Paid time off and up to 12 paid holidays - which total about 4 weeks for new full-time employees and about 2.5 weeks for new part-time employees annually
Paid parental and family leave
Family building benefits
Back-up care
Enhanced family support
Childcare subsidy
Tuition assistance
College coaching
Short- and long-term disability
Voluntary AD&D; coverage
Voluntary accident coverage
Voluntary life insurance
Voluntary disability insurance
Voluntary long-term care insurance
Mobile service & home internet discounts
Pet insurance
Access to commuter and transit programs
High School Diploma/GED (Required)
6 months of customer service and/or sales experience
At least 18 years of age
Legally authorized to work in the United States
Retail environment preferred.

89% of jobs ask for a resume

Don't let the perfect job slip away—upload your resume and we'll personalize your results instantly.

89% of jobs ask for a resume

Don't let the perfect job slip away—upload your resume and we'll personalize your results instantly.

Recommended
Flexible Driving Gig – $10,000 Guarantee + Bonus

Veyo

Milwaukee, WI 53202

$1,000 bonus
Flexible Schedule
Profile builder
Answer questions related to your search and surface your matches.
Browse Jobs
  • Jobs in Top Cities
  • Jobs by State
  • Jobs by Title
  • Jobs by Category
Tools
  • Free Resume Builder
  • Jobs2Careers+ Extension
Company
  • Post a Job
  • About
  • Advice
  • Contact
Jobs2Careers Powered by Talroo© 2026 Jobs2Careers
Logos provided by Logo.dev
© 2026 Jobs2Careers
Privacy PolicyTerms of UseYour Privacy ChoicesCalifornia Consumer Privacy Act (CCPA) Opt-Out Icon
Jobs2Careers Powered by Talroo