Discover Your Next Chapter at Obie

At Obie, we’re not just improving insurance for real estate investors—we’re building a team fueled by bold ideas and real impact.

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Trusted by thousands of teams

A recognized leader in
tech, insurance and people

While we’re proud to be recognized as a leader in tech and insurance, these accolades truly reflect our commitment to fostering a workplace where innovation thrives, employees feel valued, and success is shared by all.

A culture where
everyone belongs

We embrace curiosity, celebrate learning, and ensure every voice is heard. At Obie, we believe inclusion and collaboration are the keys to growth.

Megan Casebier

UX Researcher & Designer

“Working at Obie, I feel both challenged and supported. I look forward to working with my team on a daily basis and feel I am contributing to something meaningful.”

Find your place at Obie

Guided by our values

How we treat our customers, our teammates, and ourselves.

Do Good

From the insurance process to employee well-being, we’re committed to leaving things better than we found them.

Be Curious

We challenge ourselves to ask hard questions and explore new possibilities.

Play Fair

We value all respectful opinions, ensuring every voice is heard.

Stay Flexible

We adapt and innovate to introduce new ideas and solutions.

Benefits that support you inside and out

Health & Wellness

Medical

Dental

Vision

Life

Fitness Stipend

Telehealth

Financial & Lifestyle

401(k) Matching

Paid Parental Leave

Pet Insurance

Hotel Discounts

L&D Stipend

Flexible Time Off

Open roles at Obie

Insurance Customer Service Representative II

Those successful in this role have the ability to critically think, have a strong intellectual curiosity and a desire to help others...

Chicago, IL / Remote (US)

Come Work for Obie!

If you are interested in working at Obie but don't see a current position that fits your background, please apply...

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Obie Insurance Services, LLC - License #'s

AK #3001323846

AL #3000908445

AR #3000916052

AZ #3000916073

CA #6002583

CO #648689

CT #2716551

DC #3001009541

DE #3001247094

FL #L109506

GA #213072

HI #534451

IA #3000916206

ID #838797

IL #3001410691

IN #3563275

KS #845129262-000

KY #1091384

LA #863278

MA #2141684

MD #3000916120

ME #AGN378956

MI #128349

MN #40736335

MO #3000915661

MS #15040365

MT #3001247095

NC #1000712051

ND #3001247091

NE #3001266894

NH #3001152116

NJ #3001232518

NM #3002380649

NV #3562275

NY #1638380

OH #1313308

OK #3000916108

PA #953805

PA #1027420

PA #1038898

RI #3001151816

SC #3000916142

SD #10027388

TN #3001140087

TX #2538944

UT #819412

VA #148902

VT #3653729

WA #1101235

WI #3000916141

WV#3001232811

WY #460662

Obie Insurance Group, LLC - License #'s

AZ #3001495975

CA #6006652

CO #709122

FL #L114608

IL #3001410691

IN #3715685

IN #3726236

MD #3001485673

MI #134516

NJ #3001475592

NV #3715355

NV #3733855

OH #1389553

OH #1396167

OR #3001525732

PA #1027420

PA #1038898

TN #3001475594

TX #2720237

TX #2722701

UT #886292

UT #886293

VA #152131

WI #3001475580