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Roundstone Named a Winner of the Northeast Ohio
Top Workplaces 2024 Award for 5th Time in 6 Years

Roundstone Named a Winner of the Northeast Ohio Top Workplaces 2024 Award for 5th Time in 6 Years

2019
2020
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Plain Dealer Top Workplace 2023 Logo
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We are committed to creating a workplace where our employees feel valued, supported, and engaged. This award is a testament to the commitment and passion they bring to their work every day.

Roundstone President & Founder, Michael Schroeder

We are committed to creating a workplace where our employees feel valued, supported, and engaged. This award is a testament to the commitment and passion they bring to their work every day.

Roundstone President & Founder, Michael Schroeder

Watch and hear why our employees love working at Roundstone.

See Open Positions

Here’s what our employees have to say:

"My job has an impact! The work I do benefits others."
"I enjoy what I do and love working with members of my team."
"I feel like my contributions and skills are appreciated here."
"We are helping others with an important challenge of providing affordable health benefits to employees and their family members."
"Everything we do at Roundstone revolves around our core values - Live Well, Work Smarter, Own It, and Be Intellectually curious. I am pushed past my comfort zone and feel supported. I am always growing and learning. We all work towards the growth and success of Roundstone. The icing on the cake, we have fun at the same time."
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Who is Roundstone?

Founded in 2003, Roundstone is not your typical insurance company. We’re on a mission to help employers save on healthcare benefits so they can put those savings towards bettering their businesses and taking care of their employees.

We believe in affordable, high-quality healthcare for all. Our solution is an innovative self-funded group medical captive that enables small and midsize organizations to band together and purchase health benefits like the Fortune 500. The average client with Roundstone saves 20% compared to traditional fully insured plans.  

Learn more about Roundstone

Who is Roundstone?

Founded in 2003, Roundstone is not your typical insurance company. We’re on a mission to help employers save on healthcare benefits so they can put those savings towards bettering their businesses and taking care of their employees.

We believe in affordable, high-quality healthcare for all. Our solution is an innovative self-funded group medical captive that enables small and midsize organizations to band together and purchase health benefits like the Fortune 500. The average client with Roundstone saves 20% compared to traditional fully insured plans.  

Read More
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Roundstone By the Numbers

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average annual savings compared to fully-insured.

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average distribution
to captive participants.
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unspent captive premium distributed pro rata in 2022.

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latest retention rate
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Our Core Values

Live Well

Live Well

Foster a healthy mind, body, and spirit,
bringing a positive energy to all you do.

Foster a healthy mind, body, and spirit, bringing a positive energy to all you do.
Work Harder

Work Smarter

 Get things done, better.

Own it

Own It

Accountability is your middle name. Be on time,

do what you say, and finish what you start.

Accountability is your middle name. Be on time, do what you say, and finish what you start.

Intellectually Curious

Be Intellectually Curious

Always be learning. See opportunity everywhere

and have a drive to know.

Always be learning. See opportunity everywhere and have a drive to know.

A Real High-Performance Network

Roundstone employees have developed a work culture that is inclusive, friendly, and focused on success. From competing together in the Cleveland Corporate Challenge to the annual Heart Walk, plus our epic Summer Bash and Holiday parties, we’re proud to have created a supportive environment where we work hard and have fun together.

Meet the Team
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A Real High-Performance Network

Roundstone employees have developed a work culture that is inclusive, friendly, and focused on success. From competing together in the Cleveland Corporate Challenge to the annual Heart Walk, plus our epic Summer Bash and Holiday parties, we’re proud to have created a supportive environment where we work hard and have fun together.

Meet the Team
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A Better Benefits Package

We’re leaders in our industry, so naturally we look out for our employees’ best interests with a robust benefits package.

Day 1 PTO Eligibility

Roundstone PTO balances are updated annually and pro-rated if you start mid-year. This means your time is yours to use from day 1!

Dependent Care and Parental Leave

Roundstone matches contributions to this plan to allow employees to provide day-care or in-home care for their children and dependent elders at a reduced cost. Additionally, we understand the importance of family. We provide 2 weeks paid leave to spend time bonding with a new child, whether through child birth, adoption or foster care placement.

Tuition Reimbursement

Roundstone reimburses you for pursuing the education to advance your career. Whether the reimbursement is for a single class or applied towards a degree program, we want to support your success!

Medical, Dental and
Vision Benefits

Roundstone offers a full range of benefits, including a self-funded health plan, prescription drug benefit, dental plan, and vision plan. Roundstone even contributes toward medical expenses through an HSA and awards wellness program discounts on monthly premiums for participating employees.

Annual Bonus

Roundstone’s success is your success. Each year, employees receive up to 33% of their base compensation as a cash or retirement fund contribution, based on Roundstone’s growth and profitability. The bonus amount has been at the maximum level consistently for the past 8 years!

Good Work/Life Balance

Roundstone’s culture supports your total well-being, from providing an in-office fitness trainer and gym, to the EAP that offers financial, legal, career, and mental health support to employees free of charge. We also never miss a chance to celebrate and host family-friendly events throughout the year.

Community Outreach and Sponsorships

Roundstone never misses a chance to give back to the Lakewood and Greater Cleveland communities. Throughout the year, get involved in volunteering and sponsored events supporting local causes.

Hybrid Work Schedule

Our hybrid work schedule offers the best of both worlds -- allowing our team members to enjoy the benefits of working from home while also fostering in-person collaboration and connection in our office space.

401(k) Plan

401(k) Plan: Roundstone matches 40% up to 8% on employee contributions to this plan.

Introduce Yourself

Each open job listing includes the option to upload a resume or apply through Indeed. You’ll also be asked to take an 8-10 minute survey as part of our culture index. This is not a test that will be evaluated pass or fail, just a chance to get to know you better.

As a growing company, we are always looking for talented, enthusiastic and hard-working people to join our team. Don’t see an open job listing that fits your skills? Complete our 2-minute questionnaire to join our employment pipeline and we’ll keep you informed of future job openings that may be a good fit for you.

Introduce Yourself Below

If you feel your talent and skills fit with our fast-paced, problem-solving culture, please send your resume to hr@roundstoneinsurance.com.

Current Positions Available:

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