Roundstone

Name

Roundstone

Legal name

Roundstone Management, Ltd.

Website

https://roundstoneinsurance.com

Company type

Private

Founded year

2003

Operating status

Operating

Headcount range

101–250 employees

Ownership category

akta.pro rank

Product category

Group Captive Health Insurance

NAICS

Insurance Carriers (5241), Reinsurance Carriers (52413), Insurance and Employee Benefit Funds (5251)

SIC

Hospital & Medical Service Plans (6324), Accident & Health Insurance (6321)

akta.pro primary industry

Self-Funded (ASO) Group Health Plans & Stop-Loss (FSAIAFAB)

akta.pro secondary industries

Stop-Loss & Excess Loss Coverage (Employer Sponsored) (HLAEAAAF), Stop-Loss & Reinsurance Administration (Captive/Level-Funded Support) (HLAEALAB)

Keywords

• Captive insurance
• Self-funded health plans
• Group medical captive
• Stop-loss insurance
• Employee benefits management

Headquarters

HQ city

Lakewood

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Marketing or Sales, Operations, Technology or R&D, Infrastructure

Revenue model

1. Captive Insurance Premiums: Employers contribute premiums to the captive pool to cover predictable healthcare claims and fund the risk-sharing arrangement. Premiums are pooled across all participating employers.
2. Stop-Loss Insurance: Stop-loss insurance policies protect against catastrophic claims above predetermined thresholds. An A.M. Best 'A+' rated carrier issues stop-loss policies covering claims above specific and aggregate attachment points.
3. Collateral Management: Employers post collateral (typically less than 10% of stop-loss premium or 2% of fully insured premium) to secure their participation in the captive. Collateral earns investment income and may be refunded based on underwriting results.
4. Underwriting and Captive Management Fees: Predetermined fees included in stop-loss premium for underwriting and captive management services provided by Roundstone Management, Ltd.
5. Third-Party Administration (Bywater): Bywater provides TPA services including claims processing, member services, and plan administration for a flat per-employee-per-month (PEPM) fee.

Pricing tiers

Go-to-market motion2 records

Distribution channels2 records

Marketing channels8 records

Core offering

Roundstone operates a group captive insurance model that pools small and mid-sized employers (25 to 1,000+ employees) together to share risk and reduce healthcare costs. The captive reinsures risk between employer deductibles and $500,000, layered with stop-loss insurance covering larger claims, and is administered through Bywater, Roundstone's in-house TPA. The model returns 100% of unused premiums to employers, guarantees savings, and pairs with cost-containment solutions to deliver approximately 25% lower total annual cost versus the industry average.

Product overview

Roundstone is a group captive health insurance company offering a self-funded insurance platform that pools small and mid-sized employers (25-1,000+ employees) together to share risk and achieve guaranteed savings. The core offering is the Roundstone Group Captive Insurance model, which layers stop-loss insurance (specific and aggregate) over a captive pool covering claims up to $500,000. The portfolio centers around Bywater, Roundstone's in-house Third-Party Administrator (TPA) sub-brand handling claims processing and plan administration, paired with a Preferred Bundle combining Bywater, the Cigna network, and select PBMs (TrueRx, Serve You Rx). Supporting modules include Savings Accelerator (data-driven cost containment), Roundstone Reporting (real-time claims transparency), Roundstone University (advisor education), the Healthcare Forward Podcast, and an Advisor Toolkit. The model returns 100% of unused premiums to employers, offers guaranteed savings over five years, and achieves approximately 25% lower total annual costs versus the industry average.

Differentiator

Problem solved

Functional benefit

Brands

• Bywater: Roundstone's in-house Third-Party Administrator (TPA) that provides claims processing, plan administration, and cost containment solutions for self-funded health insurance programs.

Products and services

• Roundstone Group Captive Insurance Roundstone's core self-funded group medical captive insurance model that pools small and mid-sized employers (25 to 1,000+ employees) together to share risk, improve cost predictability, and deliver guaranteed savings versus traditional fully insured plans. The captive reinsures risk between employer deductibles and $500,000, with stop-loss insurance covering larger claims.
• Bywater Third-Party Administration (TPA) Roundstone's in-house Third-Party Administrator offering claims processing, plan administration, and member services. Delivers approximately $12,182 Per Employee Per Year (PEPY) cost versus a $17,369 national average, with 99% claims accuracy and 14-day processing, billed on a flat per-employee-per-month (PEPM) fee with no percentage-based charges.
• Stop-Loss Insurance Insurance protection layered within the captive model covering specific high-cost claims and aggregate losses. Specific stop-loss covers individual claims above employer deductibles (typically $25,000-$75,000), while aggregate stop-loss activates when total claims exceed 125% of projected costs. The captive pool itself covers mid-size claims up to $500,000, with policies issued by an A.M. Best 'A+' rated carrier.
• Roundstone Preferred Bundle Strategic combination of Bywater TPA, Cigna provider network, and select pharmacy benefit managers (TrueRx, Serve You Rx) designed to deliver optimal cost outcomes. Groups using this bundle average $10,810-$12,385 PEPY, approximately $1,700 less than standard arrangements and 24-34% below industry benchmarks.
• Savings Accelerator Data-driven cost containment platform offering three tiers of fully vetted solutions to tackle and prevent larger claims. Covers preventative medicine, telehealth, cancer care, and alternative drug sourcing to help employers reduce claims costs proactively as a complement to the captive insurance offering.
• Roundstone University Educational platform for insurance advisors to learn the value of captive health insurance, featuring resources to educate clients and confidently position self-funded insurance solutions. Includes certification programs and is accessible at roundstoneuniversity.org.

Quantifiable outcome

• 25% lower total annual cost compared to industry average
• +6 more outcomes

Named customers4 records

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration7 records

Feature4 records

Partnerships

Eight partnerships are on record, tiered core and minor.

• TrueRxcoreTechnology or IntegrationTransparent Pharmacy Benefit Manager (PBM) partner included in Roundstone's preferred bundle. TrueRx provides prescription drug negotiation, formulary management, and pharmacy claims processing as part of the integrated captive solution.
• SHARxcoreTechnology or IntegrationPrescription drug sourcing solution for high-cost specialty medications. Helps employers access alternative sourcing for expensive prescriptions to reduce pharmacy costs.
• Rightway HealthcarecoreTechnology or IntegrationDigital wellness and telehealth platform partner providing care navigation and virtual healthcare access. Rightway helps employees make better healthcare decisions and access appropriate care settings.
• CignacoreTechnology or IntegrationProvider network partner offering national network access for employer health plans. Cigna network allows employees to maintain relationships with existing healthcare providers.
• Verified TPAs and PBMscoreTechnology or IntegrationNetwork of preferred third-party administrators and pharmacy benefit managers that have been vetted for transparency, value, and service quality to deliver optimal outcomes for captive participants.
• Color HealthminorStrategic or Co-development PartnerCancer care partner featured in the Healthcare Forward podcast, discussing early intervention models for cancer care that deliver greater financial and human impact.
• Maple HealthminorStrategic or Co-development PartnerDirect Primary Care partner featured in podcast discussing how DPC reimagines patient-provider relationships and delivers more personalized, accessible care.
• University HospitalsminorStrategic or Co-development PartnerHealthcare system partner featured in podcast discussing innovation, AI, and smart hospital initiatives that can impact employer healthcare costs and outcomes.

Scale indicators10 records

Recent moves1 record

Expansion highlights5 records

Direct peers

• The Kempton Group: The Kempton Group operates group medical captive programs for SMB employers, closely mirroring Roundstone's pool-based approach with stop-loss coverage and broker distribution.
• Sun Life Financial (Stop-Loss Division): Sun Life's U.S. stop-loss and health solutions business serves the same SMB self-funded market as Roundstone, offering stop-loss coverage and group captive arrangements. Competes head-to-head for employer and broker relationships in the same distribution channels.
• Tokio Marine HCC (Stop-Loss Group): Tokio Marine HCC's Stop-Loss Group is a major provider of specific and aggregate stop-loss insurance to SMB self-funded plans, overlapping with Roundstone's stop-loss layer and captive reinsurance relationships. Both target the same benefits broker channel.
• Vitable Benefits: Vitable provides group captive and level-funded health benefits solutions targeted at small and mid-sized employers, directly competing with Roundstone's core SMB captive model and broker channel strategy.
• Oca (formerly Avante Health Solutions): Oca delivers captive and self-funded health benefit programs for SMBs through a broker distribution model. Competes directly with Roundstone on employer size, captive structure, and advisor enablement.
• Gravie: Gravie offers level-funded and self-funded health benefits designed for small businesses and competes with Roundstone for the same employer customer and broker relationships, though Gravie leans more on a marketplace technology model.

Broad incumbents

• Cigna Group (Evernorth): Cigna is both a Roundstone partner (provider network) and a broad incumbent offering competing self-funded, level-funded, and captive solutions through Evernorth. Comparable in scale and target customer (employer-sponsored health plans) but operates a much larger portfolio beyond captive insurance.
• Elevance Health (Anthem): Elevance (Anthem) offers self-funded, level-funded, and stop-loss products at national scale and competes with Roundstone across the same employer and broker ecosystem, though captive insurance is a small slice of its broader portfolio.
• UnitedHealth Group (UnitedHealthcare): UnitedHealth serves self-funded employers with stop-loss, TPA, PBM, and network solutions, providing overlapping capabilities to Roundstone's preferred bundle but at vastly larger scale across all employer segments.

Emerging players

• Sana Benefits: Sana is a smaller, technology-driven health benefits provider for SMBs that uses alternative funding and captive-like structures. Competes for the same small-employer segment with a more modern tech stack but lower scale than Roundstone.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat7 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/captiveinsurer
• YouTubeyoutube.com/roundstoneinsurance
• Facebookfacebook.com/RoundstoneInsurance
• LinkedInlinkedin.com/company/roundstone

Revenue estimate

Valuation estimate

Number of profiles

Profiles10 records

Subsidiaries1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Roundstone