Hiring Underwriters | All Experience Levels | Remote, Hybrid, or In-Office (Philadelphia HQ)

September 7, 2026

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About ParetoHealth

ParetoHealth is redefining the way employers fund healthcare. As the largest and fastest-growing benefits captive in the United States, we help thousands of small and midsize employers take control of healthcare costs through a smarter, more sustainable model.

Our mission is simple: give small and midsize employers the scale and protection they need to eliminate volatility and lower healthcare costs.

By combining data-driven insights, innovative risk management, and the collective purchasing power of our community, we enable employers to reduce volatility, improve long-term outcomes, and reinvest savings into their businesses and their people.

Headquartered in Philadelphia, ParetoHealth is growing rapidly and transforming one of the country's largest industries. Our success is fueled by talented people who are united by our four core values: Fire in the Belly, For the Greater Good, See the Field, and Get It Done Right. These values shape how we innovate, collaborate, make decisions, and deliver exceptional results for our clients and one another.

If you're energized by solving complex challenges, thrive in a high-growth environment, and want to help reshape the future of healthcare, we'd love to meet you.

Please note that ParetoHealth does not provide employment visa sponsorship for this position. Candidates must be authorized to work in the United States without sponsorship both now or in the future.

Hiring Underwriters | All Experience Levels | Remote, Hybrid, or In-Office (Philadelphia HQ)

At ParetoHealth, underwriting isn't back-office - it's front and center. Our team is the backbone of our mission to reinvent stop-loss insurance and empower midsize employers to take control of their healthcare costs. And we're growing.

Whether you're new to underwriting or bring years of experience - especially in medical underwriting, stop-loss, or self-funded plans - we want to hear from you.

What We Look For:

Experience in medical underwriting (stop-loss/self-funded plan experience is a plus)
Sharp analytical skills and comfort with data-driven decision-making
Curiosity, ownership mindset, and a desire to be part of something bigger

Why Underwriters Choose ParetoHealth:

Impact That Matters
Your decisions directly shape outcomes for thousands of lives and help employers build a long-term strategy - not just survive their next renewal.

A Community, Not a Cubicle
Join a high-performing team of curious, collaborative underwriters who love solving hard problems and building something that matters.

Real Career Acceleration
You'll get hands-on exposure, mentorship from seasoned experts, and the autonomy to grow your skills in a fast-moving, data-rich environment.

Flexibility Built Around You
Work from home, collaborate in-office, or choose a hybrid setup - with our HQ in the heart of Center City, Philadelphia.

Benefits That Go Beyond
Top-tier healthcare, competitive comp, generous time off, and benefits designed with you in mind.

At ParetoHealth, we're not tinkering at the edges of a broken system - we're rebuilding it with smarter stop-loss, aligned incentives, and a community-first model. That means no new lasers, a 30% stop-loss rate cap, and the kind of stability underwriters love to stand behind.

If you're ready to challenge the status quo, join the team that's on the right side of the fight.

Submit your resume and one of our Talent Partners will connect!

We are guided by our values:

Fire in the belly

The drive to learn, to improve, and to deliver outstanding value every day.

See the field

The ability to see the big picture and prepare to meet tomorrow's needs.

Get it done right

The passion to produce at higher rates and to the highest standards.

For the greater good

A united community creating better health benefit solutions for all.
Please note that any communication from our recruiters and hiring managers at ParetoHealth about a job opportunity will only be made by a ParetoHealth employee with an @paretohealth.com address. ParetoHealth does not conduct text message or chat-based interviews. Any other email addresses, agencies, or forums may be phishing scams designed to obtain your personal information.
We will not ask you to provide personal or financial information, including, but not limited to, your social security number, online account passwords, credit card numbers, passport information, and other related banking information until we begin onboarding activities, which will be coordinated by a member of the ParetoHealth People Ops Team with an @paretohealth.com email address.
Disclosures:
ParetoHealth is an Equal Opportunity Employer and does not discriminate on the basis of race, color, religion (creed), gender, gender expression, age, national origin (ancestry), disability, marital status, sexual orientation, or military status, in any of its activities or operations. These activities include, but are not limited to, hiring and firing of staff, selection of volunteers and vendors, and provision of services. We are committed to providing an inclusive and welcoming environment for all members of our staff, clients, volunteers, subcontractors, vendors, and clients.
California Applicants: See Pareto's CCPA Notice of Collection for California Employees and Applicants for information about how Pareto Captive Services, LLC, Pareto Health, LLC, and Pareto Underwriting Partners, LLC, together with their respective subsidiaries (collectively, "Pareto") collects and uses personal information submitted by employment applicants.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...