Roundstone

01/27/2026

We’re excited to welcome Glenn Goldney to our Leadership team as our New Chief Commercial Officer.

In his role, Glenn will oversee the performance and development of our sales organization as we continue to scale with intention and impact.

Glenn brings deep experience building and leading high-performing teams, with a proven track record in market development, leadership, and driving sustainable growth. His expertise will be a strong asset as we continue growing.

Please join us in welcoming Glenn to the team!

01/26/2026

🏆 Congratulations to Steve Sullivan, 2025 Salesperson of the Year

We’re proud to recognize Steve Sullivan as our 2025 Salesperson of the Year and the first two-time winner in Roundstone history.

Known for his consistency, positive attitude, and legendary sense of humor, Steve shows up every day with focus, optimism, and a true commitment to the work.

Well deserved, Steve. Your energy and leadership continue to raise the bar for our team. 👏

01/23/2026

Wednesday, our Regional Practice Leaders came together at the Browns Stadium for our Sales Kickoff. It was a great opportunity to connect in person and align on our annual goals.

The team heard key updates from Leadership, Sales Operations, Partner Solutions, Bywater, Customer Outcomes Managers, and Marketing. They then wrapped up a second day at Roundstone with focused discussions alongside our Underwriting team.

After a year spent building efficiency and working smarter in 2025, we’re carrying that momentum forward. Built to be better and ready for a strong, successful 2026!✨

01/20/2026

🚀 Now Hiring: Regional Practice Leader (Ohio & Michigan)

Roundstone is growing, and we’re looking for a Regional Practice Leader to build advisor relationships and drive new business across Ohio and Michigan.

This role is for a confident, competitive benefits professional who enjoys educating advisors, presenting to employer leaders, and closing business. You’ll own the sales process and help position Roundstone’s captive stop-loss program as a smarter way for employers to manage healthcare costs.

Great fit if you:
✔ Thrive in competitive sales environments
✔ Know employee benefits and want to deepen your expertise
✔ Can turn complex ideas into clear, compelling conversations

Ready to help employers take control of healthcare costs? Let’s talk.
https://roundstoneinsurance.com/about-roundstone/careers/?utm_source=Facebook&utm_campaign=RPL&utm_id=Webpage

01/15/2026

💡 Hard-Earned Know-How Matters

Did you know your close rate can jump up to 40% when a Roundstone Regional Practice Leader (RPL) presents alongside you?

Here’s where advisors see the difference:

Our RPLs bring experience you can’t fake. They’ve worked across states, plan designs, underwriting conversations, and complex claims situations. They’ve seen what works, what breaks, and how to navigate tough moments when it matters most.

From sharing real-world solutions to leveraging advocacy programs that advisors may not know exist, RPLs add depth and credibility to the conversation. Many have been on the advisor side before, so they understand the pressure points between the carrier, broker, and client, and they don’t sugarcoat the answer just to win the room.

That honesty builds trust.
And trust closes business.

👉 Bring an RPL into your next meeting and see the impact for yourself. https://roundstoneinsurance.com/contact-us/?utm_source=Facebook&utm_campaign=HEKH&utm_id=Webpage

01/14/2026

Wellness programs are often dismissed as “nice to have.”
The data tells a very different story.

When designed intentionally, wellness programs reduce healthcare costs by addressing the biggest drivers of spend, not by adding surface-level perks. Real return on investment starts with prevention.

Early detection changes outcomes.
Health screenings and biometric assessments help identify risks before they turn into chronic conditions that require years of care. Preventing just one case of type two diabetes can save nearly $10,000 per year. Just as important, early identification helps people avoid painful complications and stay healthier without a diagnosis defining their daily lives.

Chronic condition management prevents costly setbacks.
For individuals managing conditions like diabetes, structured support helps maintain stability and avoid high-cost events such as hospitalizations, ER visits, or secondary complications. For organizations and advisors guiding plan design, this stability translates into fewer disruptions, more predictable claims, and better long-term outcomes.

Mental health support stops problems from escalating.
Early intervention for anxiety and depression reduces the likelihood of hospitalization, long-term disability, or extended time away from work. Plans that prioritize mental health support protect both people and performance by addressing issues before they turn into crises.

The impact goes beyond claims.
Organizations with comprehensive wellness strategies often see 28% fewer sick days, lower turnover, and stronger recruiting advantages. Advisors see the difference in client retention and long-term plan sustainability. People feel it in healthier cultures, less burnout, and benefits that genuinely support daily life.

The takeaway is simple. Wellness works when it’s strategic, measurable, and tied to real outcomes. When prevention and early intervention are built into plan design, wellness becomes a cost-control strategy and a meaningful investment in people.

The question isn’t whether wellness programs work.
It’s whether your program is designed to deliver real ROI for both the company and its employees.

Interested in learning more? Check out our most recent blog: https://roundstoneinsurance.com/blog/wellness-programs-impact-bottom-line-analytics/?utm_source=Facebook&utm_campaign=Blog&utm_id=Webpage

01/13/2026

This week, our leadership team is in San Francisco for their annual meeting. Time set aside to reflect, collaborate, and focus on what’s ahead for our team and the clients we serve. We’re excited about the momentum ahead and what 2026 will bring!

01/12/2026

Your Premiums. Your Control. Your Savings.

Think of a captive like a group savings plan for healthcare.

Instead of sending all your premium dollars to an insurance carrier, employers band together, share risk, and keep more control over how their plan works.

When claims are lower, the savings stay with the group, not the carrier.

Simple idea. Big impact.

Curious how a captive could work for your team? Let’s talk.
https://roundstoneinsurance.com/contact-us/?utm_source=Facebook&utm_campaign=1-12&utm_id=Webpage

01/09/2026

Primary care shouldn’t feel rushed, hard to access, or impersonal. Yet for many employees, that’s the norm.

🎙️ In our newest episode of Healthcare Forward, Michael Schroeder sits down with Dr. Berry, Direct Primary Care clinician at Maple Health, to explore how Direct Primary Care (DPC) is reshaping the patient-provider relationship and what it means for employers.

DPC replaces the traditional fee-for-service model with a membership-based approach that prioritizes access, time, and proactive care. The result is a better experience for patients and a smarter strategy for employers.

You’ll hear:
• What makes Direct Primary Care different from traditional primary care
• How the DPC model improves access, communication, and continuity of care
• Why employers are increasingly integrating DPC into self-funded health strategies
• How DPC supports cost containment while improving employee engagement

When employees can actually see their doctor, ask questions, and get timely care, better outcomes follow.

🎧 Listen to the full episode of Healthcare Forward on YouTube, Spotify, or Apple Podcasts.
👉 Listen here:https://roundstoneinsurance.com/roundstone-mcf-2026-registration/?utm_source=Facebook&utm_campaign=Dr.BarryHCF&utm_id=Youtube

01/08/2026

Dallas, here we come. 🤠

Our 2026 Medical Captive Forum is heading to the Hyatt Regency near Union Station on May 6–7. Two days designed to help employers and advisors gain clarity, cut waste, and make more confident health plan decisions.

What you can expect:
• An empowering keynote to kick things off
• Education that’s practical, not theoretical
• Networking with hundreds of health insurance professionals

👉 Register now to join us in Dallas:
https://roundstoneinsurance.com/roundstone-mcf-2026-registration/ ?utm_source=LinkedIn&utm_campaign=MCF+Dallas&utm_id=Webpage

01/07/2026

Why do employers feel stuck at renewal?

Many fully insured plans offer simplicity, but not transparency. Employers pay the premium, absorb rising costs, and rarely see what is actually driving claims.

Regional Practice Leader Jack Schroeder explains how self-funding changes the equation by giving employers access to their data and greater control over healthcare costs.

Contact a Regional Practice Leader to learn how to take control of your data and make more informed benefit decisions for you or your clients’ plan: https://roundstoneinsurance.com/contact-us/?utm_source=Facebook&utm_campaign=FAQ-Jack&utm_id=Webpage

01/05/2026

We’re growing in Northern California & Northern Nevada and looking for a Territory Salesperson (Regional Practice Leader) to help lead the charge.

At Roundstone, we partner with advisors to help employers rethink healthcare benefits through smarter, more transparent captive solutions. This role is about building relationships, winning new business, and closing deals in a competitive, high-impact territory.

This could be a great fit if you thrive on:
✔ Developing and expanding broker relationships
✔ Presenting confidently to advisors and employers
✔ Owning the sales process and driving results
✔ Turning complex benefits strategies into clear, compelling stories

This role is ideal for a driven benefits professional with 3–5 years of industry experience who’s ready to compete, grow, and make a real impact. Travel within the territory (8–10 overnights per month) is required.

Ready to help employers save on healthcare and reinvest in their people? Let’s talk.

https://roundstoneinsurance.com/about-roundstone/careers/?utm_source=Facebook&utm_campaign=RPLJob&utm_id=Webpage

TOGETHER AT ROUNDSTONE We’re glad your search has led you here! Browse All Jobs Roundstone Named a Winner of the Northeast Ohio Top Workplaces 2025 Award for 6th Time Roundstone Named a Winner of the Northeast Ohio Top Workplaces 2025 Award for 6th Time We are committed to creating a workplace whe...