Roosevelt Road Specialty

What Roosevelt Road Specialty does

Roosevelt Road Specialty is a multi-platform specialty insurance Managing General Underwriter (MGU) that underwrites, prices, and administers niche commercial and personal lines through six programmatic platforms: Tradesman Program Managers (construction), CareAgents and K&B Specialty Insurance (senior living), Renaissance Specialty Insurance (sports and entertainment), RISE Habitational (real estate), Premium Surety Solutions and Surety Underwriting Solutions (surety bonds), with underwriting risk ultimately retained in part by its Bermuda captive, Roosevelt Road Re. The company distributes exclusively through appointed brokers and program partners, including JenCap, Monument Sports, Champion Specialty Services, Champion Elevator, and HUB Healthcare Solutions, and reaches insureds across all 50 U.S. states via Renaissance's admitted status and the broader carrier and reinsurance footprint.

Underlying technology includes an integrated program administration platform spanning underwriting, policy administration, and claims, augmented by proprietary AI tooling — most notably the FraudX anomaly and fraud-detection engine released in July 2025 — and predictive modeling used in underwriting decisions. Senior-living programs incorporate third-party AI clinical tools such as VirtuSense AI (fall prevention) and WoundRounds (wound monitoring), while the Bermuda captive provides capital efficiency and reinsurance structuring optionality. Combined premium volume across the platforms exceeds $1.3 billion.

The business model is that of a specialty MGU: Roosevelt Road earns commission and underwriting profit on premium it binds through its broker network, with risk shared across carrier partners and its own captive. Revenue is diversified across at least five specialty verticals (construction, senior living, sports and entertainment, habitational real estate, and surety), with no single insured class disclosed as dominant. Capital is sourced from a $150 million senior credit facility closed in March 2025 and from reinsurance partners, supporting reserves and continued platform expansion into new lines such as Property and surety bonds.

Name

Roosevelt Road Specialty

Legal name

Roosevelt Road Specialty

Website

https://rooseveltroadspecialty.com

Company type

Private

Founded year

2016

Operating status

Operating

Headcount range

51–100 employees

Short description

Roosevelt Road Specialty is a multi-platform specialty MGU underwriting construction, senior living, sports and entertainment, habitational, and surety risks through appointed brokers across all 50 U.S. states, with premium volume exceeding $1.3 billion and reinsurance retained via its Bermuda captive.

Ownership category

akta.pro rank

NAICS

Insurance Agencies and Brokerages (524210)

akta.pro primary industry

Insurance Program Administration & MGA/MGU Services (FSAEADAK)

akta.pro secondary industries

Contractors BOP / Artisan Package (FSAJAFAD), Habitational / Residential Property Managers BOP (FSAJAFAN), Real Estate / Lessors Risk BOP (FSAJAFAI)

Keywords

• Specialty insurance underwriting
• Managing general agent
• Construction liability insurance
• Senior living insurance
• Surety bond underwriting

Headquarters

HQ city

New York

HQ country

United States

HQ region

North America

Offices3 records

Markets served

GTM type

B2B

Offering type

Services

Cost components

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

Revenue model

1. Insurance Premium Revenue (MGA Commission and Underwriting): Roosevelt Road Specialty operates as a Managing General Agent (MGA) earning revenue from insurance premiums written through its specialty programs. The company designs and underwrites insurance programs, issues policies through A-rated carrier partners, and earns underwriting results and commission income. They also access in-house reinsurance capacity through Roosevelt Road Re to support their programs.
2. Surety Bond Premiums: Premium Surety Solutions and Surety Underwriting Solutions earn revenue from surety bond products including performance bonds, bid bonds, payment bonds, license and permit bonds, court bonds, and maintenance bonds for contractors and collateralized reinsurance companies.

Pricing tiers

Go-to-market motion2 records

Distribution channels6 records

Marketing channels4 records

Core offering

Roosevelt Road Specialty operates as a market-leading specialty Managing General Underwriter (MGU) that designs, underwrites and issues insurance programs through A-rated carrier partners for commercial trade contractors and construction (Tradesman Program Managers), senior living facilities (CareAgents by K&B), sports, leisure and entertainment venues (Renaissance Specialty Insurance), habitational real estate (RISE Habitational), and contract and commercial surety bonds (Premium Surety Solutions and Surety Underwriting Solutions), supported by in-house Bermuda reinsurance (Roosevelt Road Re) and AI-driven risk and fraud mitigation technology.

Product overview

Roosevelt Road Specialty operates as a diversified specialty MGU (Managing General Underwriter) delivering insurance solutions through multiple specialized platforms. The core portfolio includes Tradesman Program Managers (construction and trade contractors), CareAgents by K&B (senior living facilities), Renaissance Specialty Insurance (sports, entertainment, and leisure), RISE Habitational (real estate and property management), Premium Surety Solutions and Surety Underwriting Solutions (contract and commercial surety bonds), and Roosevelt Road Re (in-house reinsurance). The company provides integrated underwriting, claims management, loss control, and fraud investigation services across all platforms, backed by the resources of parent company Roosevelt Road Capital Partners.

Differentiator

Problem solved

Functional benefit

Brands

• Tradesman: Market-leading insurance solution for trade contractors specializing in general and excess liability with hands-on risk services for carpenters, electricians, HVAC installers, masons, and other construction professionals
• CareAgents
• Renaissance Specialty Insurance
• RISE
• Premium Surety Solutions
• Surety Underwriting Solutions

Products and services

• Tradesman Program Managers Market-leading specialty insurance program for commercial trade contractors and general contractors (electricians, HVAC installers, carpenters, masons, large metropolitan contractors), providing tailored general liability and excess liability coverage with hands-on risk services, loss control, real-time incident reporting, and fraud investigation capabilities. Policies issued through A-rated carrier partner Clear Blue Insurance Group with limits up to $2M/$4M primary layer, $10M total aggregate, and minimum premium $300K in NY & NJ.
• CareAgents by K&B Specialty Insurance Specialized insurance program for senior living facilities — nursing homes, assisted living, adult day care, hospice, home health care, and independent/assisted living — providing $1M/$3M limits per location with $10M aggregate, $100K minimum premium, claims-made incident-sensitive coverage, and embedded VirtuSense AI fall prevention (80%+ fall prevention) and WoundRounds wound care automation (80%+ pressure injury reduction).
• Renaissance Specialty Insurance Specialty insurance coverage for sports, entertainment and leisure operators including arenas, stadiums, entertainment venues, festivals, concerts, casinos, convention centers, performing arts venues, amphitheaters, amusement parks, family entertainment centers, gyms, trampoline parks, waterparks, and special events. Proprietary forms and rates filed on an admitted basis in 50 states with primary $2M/$4M and $3M excess placement available.
• RISE Habitational Specialized habitational risk management and property insurance program for owners, developers and property managers of apartments, condos, co-ops, townhome associations, and senior/retirement facilities. Provides general liability and excess liability (limits $1M/$2M up to $2M/$4M plus $3M excess) using predictive modeling and an AI-driven underwriting platform, with minimum premiums ranging from $150K to $250K depending on NYC borough location and limits. Available admitted/E&S in NY & NJ and E&S in 14 additional states.
• Premium Surety Solutions Surety bond program providing performance bonds, bid bonds, payment bonds, license and permit bonds, court bonds, and maintenance bonds for specialty trade contractors and collateralized reinsurance companies, available in all 50 states through appointed brokers.
• Surety Underwriting Solutions Specialty bond platform providing contract and commercial surety bonds for small to mid-sized contractors with flexible, efficient bonding solutions designed to support contractor growth.
• Roosevelt Road Re Bermuda-based Class 3B reinsurance company providing in-house reinsurance capacity, risk participation, and access to niche casualty lines of business to all Roosevelt Road Specialty MGA platforms.

Quantifiable outcome

• AI-driven underwriting platform accelerated submission-to-quote turnaround times by 23%
• +5 more outcomes

Named customers5 records

Segments5 records

Ideal customer profiles5 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

AI capability3 records

Feature7 records

Partnerships

16 partnerships are on record, tiered core and minor.

• Clear Blue Insurance GroupcoreTechnology or IntegrationClear Blue Insurance Group is the carrier partner for Tradesman Program Managers, providing the underlying A-rated insurance capacity for the program's general liability and excess liability policies issued to commercial trade contractors and general contractors.
• Gallagher BassettcoreImplementation/ SI/ Consulting PartnerThird-party administrator (TPA) for Tradesman Program Managers' GL/XS claims, CareAgents claims, Renaissance Specialty claims, and RISE claims. Provides unbiased claims management across multiple MGA platforms.
• Goldberg SegallacoreImplementation/ SI/ Consulting PartnerLaw firm serving as defense counsel for Tradesman Program Managers in claims litigation and personal injury matters.
• Pillinger, Miller, Tarallo (PMT)coreImplementation/ SI/ Consulting PartnerLaw firm serving as defense counsel for Tradesman Program Managers in claims litigation.
• Fuchs Rosenzweig PLLCcoreImplementation/ SI/ Consulting PartnerLaw firm serving as defense counsel for Tradesman Program Managers.
• Power InvestigationscoreImplementation/ SI/ Consulting PartnerInvestigation firm supporting Tradesman's Special Investigative Unit (SIU+) and Criminal Investigative Unit (CIU) in combating insurance fraud.
• VirtuSensecoreTechnology or IntegrationAI technology partner for CareAgents senior living program. VirtuSense's AI sensors detect movements to predict falls 60 to 90 seconds before they happen, preventing more than 80% of falls for senior living clients.
• WoundRoundscoreTechnology or IntegrationAI-powered wound care technology partner for CareAgents. WoundRounds reduces in-house acquired pressure injuries by over 80% and delivers expert wound nurse support via smartphone app to the bedside virtually and in real time.
• Network Adjusters, Inc.coreImplementation/ SI/ Consulting PartnerThird-party administrator for Tradesman Program Managers' auto claims.
• Roosevelt Road Capital PartnerscoreOthersParent company and investor. Roosevelt Road Capital Partners (RRCP) is the global insurance organization that wholly owns all RRS MGA platforms and Roosevelt Road Re reinsurance company. Provides substantial resources and reinsurance access.
• International Risk Management Institute, Inc. (IRMI)minorOthersProud member of IRMI, providing access to risk management resources and industry expertise.
• American Property Casualty Insurance Association (APCIA)minorOthersProud member of APCIA, the major trade association for the property and casualty insurance industry.
• Target MarketsminorOthersProud member of Target Markets, a trade association for program business insurers and MGAs.
• IBA NYminorOthersProud member of IBA NY (Insurance Brokers Association of New York).
• Coalition of Asian American Leaders (CAALF)minorOthersRoosevelt Road Specialty is affiliated with CAALF, a coalition focused on supporting Asian American women in the insurance industry.
• AGC of New York StateminorOthersAffiliated with AGC of New York State, the Associated General Contractors of America chapter serving New York.

Scale indicators14 records

Recent moves11 records

Expansion highlights6 records

Direct peers

• Burns & Wilcox: Specialty insurance broker and MGA operator serving high-hazard and niche commercial lines including construction, real estate, and hospitality. Comparable as a specialty-focused MGU with curated broker distribution and program expertise in underserved verticals.
• Risk Placement Services (RPS): Specialty wholesale insurance broker and MGA platform serving construction, real estate, hospitality, and entertainment risks. Comparable as a multi-line specialty MGU with binding authority and program management capabilities similar to Roosevelt Road's model.
• Amwins: Largest independent specialty insurance wholesale distributor and MGA in the US, operating across multiple specialty lines including construction, real estate, and hospitality. Directly comparable as a multi-vertical specialty MGU with curated broker distribution and proprietary programs.
• CRC Group: Specialty wholesale insurance distributor operating across diverse verticals including construction, real estate, hospitality, and entertainment. Directly comparable as a specialty MGU/wholesaler with multiple program businesses and broker-centric distribution.
• Palomar Holdings: Specialty insurer focused on niche markets including earthquake, hurricane, and specialty casualty. Comparable as a specialty-focused insurance platform with similar target market approach and capital-light underwriting philosophy.
• Skyward Specialty Insurance Group: Specialty property and casualty insurer with multiple MGA platforms across casualty, property, and surety lines. Closely comparable to Roosevelt Road as a specialty insurance platform with a multi-program MGA structure and similar scale (~$1.3-1.7B premium range).

Broad incumbents

• Markel Corporation: Large specialty insurer with diversified program business across construction, real estate, entertainment, and surety lines. Comparable at the specialty program business level, though Markel is significantly larger and broader in scope than Roosevelt Road.
• Tokio Marine HCC: Specialty insurance group within Tokio Marine operating across multiple niche casualty and property lines. Comparable as a multi-line specialty insurer/MGU, though substantially larger and more diversified than Roosevelt Road.
• Hiscox: Specialty insurer with MGA-style operations across professional liability, cyber, and specialty casualty. Comparable at the specialty product level (senior care, construction, entertainment adjacencies), though much larger and globally diversified.

Emerging players

• Accelerant: Data-driven specialty insurance platform enabling MGA partners through shared underwriting intelligence and reinsurance access. Comparable as an emerging specialty MGA-enabling platform, with partial overlap in construction, real estate, and commercial specialty verticals.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat6 records

Key risks6 records

Key highlights7 records

Customer concentration

• LinkedInlinkedin.com/company/roosevelt-road-specialty

Revenue estimate

Valuation estimate

Number of profiles

Profiles16 records

Subsidiaries7 records

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 Roosevelt Road Specialty