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Do What You Love.
Love What You Do.

We know what you’re thinking – insurance is boring. But we don’t use the “B” word around here. While we’re serious about our work – we don’t take ourselves too seriously. We love to laugh and live by the Work Hard, Play Hard mentality. 


Since 2007, we’ve strived to create an environment that makes people excited to come to work. Like that old cliché says, we’re a family. It’s no secret we value our employees, which is why we’ve been voted one of Hampton Road’s “Best Places to Work” and have maintained a 95% retention rate. 

Competitive pay, work-life balance, great benefits, family atmosphere, relaxed work environment, volunteering, and CHEESE (you’ll understand soon) are a few of our favorite things. In fact, Cheese means so much to us that we made it a core value.

Available Positions

We’re Totally Cheese

Let us explain. Cheese has a totally different meaning here at Prosper. We’re not talking about fondue. Cheese is a way of life. It’s an attitude, the feeling of HECK YEAH, and that’s totally rad. 

Behind our doors, you’ll find amazing people who are dedicated to making the insurance industry enjoyable. We believe in thinking outside of the box and drawing outside of the lines. We’re the perfect mix of fun and driven, sophisticated and casual, playful and professional. And we care about our people the same way we care about our clients- because everyone deserves to Prosper.

Check out Prosper’s YouTube channel!

The Perks

Our unique culture and family atmosphere isn’t the only reason to work at Prosper. We also offer a full range of benefits to support you and your family and ensure you have an excellent work-life balance.  

  • Education & Development

    We understand that humans are constantly evolving.  Through workshops, trainings, or industry certifications, we’re here to support your personal and professional growth.

  • Compensation

    Whether you are a salary paid employee or commissioned, we pride ourselves on being industry leaders in our total compensation packages.

  • Family Planning

    We love seeing our employee’s families grow!  Prosper provides paid maternity and paternity leave and provides support through our Adoption Assistance Program.

  • Wellness

    Exercise? I thought you said extra fries. While food makes us happy too, regular exercise has many health benefits. That’s why we pay the full cost for a gym membership for all employees.

  • Time Off

    At Prosper we believe in a healthy work-life balance.  All full-time employees receive three weeks paid vacation on day one of employment.  You can finally take that trip to Hawaii!

  • Financial Security

    We help our clients plan for the future, so why wouldn’t we help our employees too?  Prosper offers a 401k retirement plan to all full-time employees.  We will even match some of your contributions!

  • Benefits

    We offer affordable health, dental, and vision plans for you and your family with no waiting period. We also provide company paid disability and life insurance for all full-time employees.

  • Inclusivity

    Prosper is committed to continuing to make diversity, equity, and inclusion part of everything we do—from the products we sell to how we build our team. That’s why we have a council dedicated to Diversity and Inclusion initiatives to ensure our employees feel comfortable expressing themselves. We want our employees to feel fulfilled and valued, and that doesn’t stop at their job description.

Teammate Testimonials


“At Prosper you are not a co-worker, you’re a family member.  Prosper’s culture makes agents feel welcome to be themselves and sell as themselves.  Whether it is after hours’ activities or our annual Spanksgiving celebration, you will always feel like you’re a part of the family.”

Chris ‘Bear’ Kennedy Sales Manager

“Prosper continues to go the extra mile even in a virtual setting and that’s helped this whole pandemic breeze by.”

Aerial Johnson Service Agent

“Being in a positive workplace is very important to me.  Prosper encourages personal growth, working hard, empowering one another and sprinkles a lot of excitement on top!”

Jessica Fitzgibbons VP of Company Growth

“I have been working with Prosper for approximately 3 years and I love it. I have made some lifelong work proximity buddies! Everyone is genuine and takes care of each other like family. “

Anand Manivannan Sales Agent

“I have never worked for a company that says they are like a family and then exemplifies it. From the owners to service team, everyone here is treated with respect.”

Casey Allen Receptionist

“I have worked here for over six years, and I still look forward to coming to work every day.”

Mike Ferros Team Lead

Workplace Awards

Not to brag, but…

Let’s Grow Together

We’re constantly growing which means we’re always looking for awesome people to join our team. 
Maybe you’ve fallen into a position where you’re feeling a bit stagnant and lacking some professional development?
We want to meet you! Don’t have experience in insurance?  We’ll train you! 
Let’s chat!  

Sound Cheese? Check out our current open positions and apply today. 

View Positions

Don’t see a current opening that fits your skillset?
We still want to talk to you!

Please reach out to our Talent Acquisition Specialist,
Pamela Camper:

The information available on this website does not constitute a guarantee of employment. Prosper Insurance is an equal opportunity employer. Prosper Insurance provides equal employment opportunities to all applicants for employment and prohibits discrimination of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity, or any other characteristic protected by federal, state or local laws.

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