What ITOO Special Risks does

iTOO Special Risks (Pty) Ltd is a South African specialty insurance underwriter operating as the preferred specialty-products underwriter for The Hollard Insurance Company Limited, its parent and paper provider. The company designs and underwrites a broad portfolio of specialist lines organized into clusters — Cyber, Art & Entertainment, Professions, Business, Specialty, and Crisis — spanning products such as Commercial Cyber, Medical Malpractice, Clinical Trials, Directors & Officers Liability, Event Liability, Aviation, Drones, Kidnap & Ransom, and Political Violence & Terrorism. It serves both commercial and personal risk needs (the latter via [My]Cylution personal cyber cover) and traces its operating origins to the 2015 acquisition of Etana Special Risks, Hollard Liability, and Hollard Film Guarantors under iTOO Investments.

The business runs a broker-intermediated distribution model, partnering with over 1,000 brokers across South Africa and selected African markets (Namibia, Botswana, Mozambique, Kenya). It supports this channel with broker enablement infrastructure: CPD-accredited "iTOOsday" webinars (44 delivered in the 2024/25 cycle, ~23,561 attendees, ~1.4M CPD hours), thought-leadership content (The Hub, The Expert Magazine, The Expert Studio podcast), and digital access platforms including EazEvent (streamlined Event Liability quote-and-bind), Single URL (a consolidated product portal launched 2025), and SureThing (a packaged all-risk liability product for SMBs, launched 2022, with a SureThing Stride variant for coaches/running clubs priced from R450/month).

Revenue is generated through specialty insurance premiums earned across its underwriting lines, with Hollard providing the underwriting balance sheet. Pricing is largely undisclosed and broker-quoted per risk; disclosed retail signals (e.g., SureThing Stride from R450/month) indicate a subscription-style, recurring premium mechanic at the SMB/individual end. The company has grown through both organic product launches and bolt-on M&A (Hollard Court Bonds 2018, Renew Risk Africa 2020, Envirocare 2023) and joint ventures (Tokio Marine HCC, 2018, in Events Liability and Kidnap & Ransom). Leadership includes Chairman Paolo Cavalieri, an Etana co-founder with ~40 years of insurance experience, and CFO Matlhogonolo Zulu, a chartered accountant leading the firm's BBBEE transformation.

Name

ITOO Special Risks

Legal name

iTOO Special Risks (Pty) Ltd

Website

https://itoo.co.za

Company type

Private

Founded year

2015

Operating status

Operating

Headcount range

101–250 employees

Short description

South African specialty insurance underwriter and Hollard's preferred specialty-products underwriter, distributing niche commercial and personal lines (cyber, professional, event, crisis, aviation) through 1,000+ brokers across South Africa and selected African markets.

Ownership category

akta.pro rank

Product category

Specialty Insurance

NAICS

Direct Insurance (except Life, Health, and Medical) Carriers (52412), Other Insurance Related Activities (52429)

SIC

Fire, Marine & Casualty Insurance (6331), Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Professional Liability (E&O) (FSAJAGAC)

akta.pro secondary industries

Fine Art, Jewelry & Specie (FSAJAGAL), Embedded Insurance & Affinity Distribution Platforms (FSAGAGAL), Product Liability (FSAJADAC)

Keywords

• Specialty insurance underwriting
• Cyber liability insurance
• Professional indemnity coverage
• Event liability insurance
• Specialty risk distribution

Headquarters

HQ city

Parkton

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

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

Revenue model

1. Specialty Insurance Underwriting: iTOO operates as Hollard's preferred underwriter of specialty insurance products, generating revenue through insurance premiums across multiple specialty lines including Cyber, Art & Entertainment, Professions, Business, Specialty, Crisis, and Hollard Solutions.

Pricing tiers

Go-to-market motion1 record

Distribution channels4 records

Marketing channels9 records

Core offering

iTOO Special Risks underwrites and distributes specialty insurance products across Cyber, Art & Entertainment, Professions, Business, Specialty, and Crisis categories, with policies underwritten by The Hollard Insurance Company Limited. Products are sold primarily through a broker network of over 1,000 brokers across South Africa and selected African regions, supported by digital platforms (EazEvent, Single URL) and CPD training (iTOOsday).

Product overview

iTOO Special Risks operates as a specialty insurance provider and preferred underwriter of specialty products for Hollard Insurance. The company offers a comprehensive portfolio of specialty insurance products organized into distinct clusters: Cyber (Commercial Cyber, [My]Cylution), Art & Entertainment (Art, Classic Car, Commercial Fine Art Dealers & Auctioneers, Contingency, Event Liability, Hole in One, Photography, Prize Indemnity), Professions (Medical Malpractice, Clinical Trials, Professional Indemnity, VetProtect), Business (Broadform Liability, Commercial Crime, Directors & Officers Liability, Employment Practice Liability, Financial Institutions Crime & Civil Liability, SureThing, SureThing Stride, Trustee Liability), Specialty (Aviation, Drones, Environmental Liability, Renew Risk, Schemes/Binders and Outsourced Agreements), Crisis (Kidnap & Ransom, Political Violence & Terrorism), and Hollard Solutions. The company also offers digital platforms including EazEvent for streamlined Event Liability insurance access and Single URL for consolidated digital product access. iTOO partners with over 1,000 brokers across South Africa and selected African regions, offering both traditional specialty insurance products and digital-first solutions.

Differentiator

Problem solved

Functional benefit

Brands

• [My]Cylution: Personal Cyber Insurance - protects individuals against cybercrime, identity theft, online fraud, cyber extortion, and digital threats
• EazEvent
• SureThing
• RUN99
• The Expert Magazine
• iTOOsday
• The Expert Studio

Products and services

• Commercial Cyber Cyber insurance providing businesses access to expert knowledge and resources in managing cyber incidents, from lost devices to deliberate cyber-attacks.
• [My]Cylution Personal cyber insurance protecting individuals against cybercrime, identity theft, online fraud, cyber extortion, and digital threats from everyday internet usage.
• Event Liability Specialist event liability insurance protecting organizers against claims from guests, spectators, and attendees at events.
• EazEvent Digital platform designed to simplify access to Event Liability insurance for event organizers across South Africa's dynamic events landscape.
• Single URL Streamlined digital access point bringing all iTOO Special Risks digital products together in one intuitive platform for brokers and clients.
• SureThing All-in-one, all-risk third-party legal liability solution designed for small businesses, combining professional indemnity, public liability, defamation, and cyber liability.
• SureThing Stride All-in-one, all-risk third-party legal liability solution designed specifically for athletics coaches and running clubs, covering professional indemnity, public liability, defamation, cyber liability, D&O, and employment practices liability. From as little as R450 per month.
• Medical Malpractice Coverage for medical practitioners and institutions against allegations of negligence, errors, omissions, and professional liability claims.
• Clinical Trials Specialized insurance protecting organizations conducting clinical trials from unique risks and liabilities, including participant injury, illness, or death during trials.
• Professional Indemnity Specialist cover for professionals against third-party claims arising from advice or services provided.
• Directors & Officers Liability D&O insurance protecting directors and officers against personal liability for management decisions.
• Kidnap & Ransom Coverage for businesses and individuals against kidnapping, extortion, and ransom risks, particularly relevant for international travel to unstable regions.
• Aviation Specialty aviation insurance offering a strengthened-capacity, personalized-solutions approach to underwriting for the complex aviation industry.
• Environmental Liability Coverage for environmental risks and liabilities faced by businesses.
• Renew Risk Specialty risk insurance product acquired from Renew Risk Africa, serving the environmental and renewable energy sector.

Quantifiable outcome

• Over 1000 brokers partnered across South Africa and selected African regions
• +1 more outcomes

Named customers4 records

Segments7 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

Seven partnerships are on record, tiered core and minor.

• Armata Cyber SecuritycoreGTM or Marketing Partner · 1 January 2024Strategic partnership formed between Armata Cyber Security and iTOO Special Risks to add further value to one another's customers. Collaboration marked by professionalism, thoroughness, and shared vision to safeguard customers from cyber threats. Partnership focuses on cyber insurance solutions delivery.
• EthiQalcoreTechnology or Integration · 1 January 2024Partnership established with EthiQal in 2024 as part of iTOO's strategic expansion and product development initiatives.
• Tokio Marine HCCcoreStrategic or Co-development PartnerJoint ventures established in 2018 with Tokio Marine HCC in Events Liability and Kidnap & Ransom product lines, enabling iTOO to expand specialty coverage offerings.
• Hollard Insurance Company LimitedcoreOthersiTOO operates as Hollard's preferred underwriter of specialty products. All insurance products are underwritten by The Hollard Insurance Company Limited (Reg. No. 1952/003004/06), a licensed non-life insurer and authorized financial services provider.
• Hollard Trade CreditcoreStrategic or Co-development PartnerHollard Trade Credit was founded by iTOO in 2016 as part of its product expansion strategy. The company acquired Renew Risk Africa in 2020, expanding trade credit capabilities.
• Winemag.co.zaminorGTM or Marketing PartneriTOO sponsors the Next Generation Awards convened by Winemag.co.za to recognize young standout winemakers under 35 years of age. Melissa Brink, Underwriting Lead at iTOO, presented awards at the 2026 ceremony.
• Osprey PartnershipcoreStrategic or Co-development PartneriTOO launched the Osprey Partnership in 2025 as part of its strategic partnership expansion initiatives.

Scale indicators4 records

Recent moves11 records

Expansion highlights6 records

Direct peers

• SHA Risk Specialists: South African specialist underwriting manager focused on liability and professional lines distributed through brokers, directly overlapping iTOO's professions and business liability clusters and UMA model.
• Camargue Underwriting Managers: SA specialist underwriting management agency offering niche liability, film/entertainment, and specialty covers via brokers, competing directly for the same broker shelf-space and specialty lines as iTOO.
• Constantia Insurance Group: South African niche/specialty insurance group operating multiple underwriting managers across specialist lines, comparable to iTOO's multi-cluster specialty model.

Broad incumbents

• Bryte Insurance: Large SA commercial and specialty P&C insurer distributing through brokers, overlapping iTOO's commercial liability and specialty offerings as a broader incumbent.
• Santam: South Africa's largest short-term insurer with specialist divisions and broker distribution, a broad incumbent competing across many of iTOO's commercial and specialty lines.
• Old Mutual Insure: Major SA P&C insurer with niche/specialist underwriting units and broker channel, overlapping iTOO's commercial and specialty products at larger scale.
• Tokio Marine HCC: Global specialty insurer across professional, contingency, and K&R lines; a joint-venture partner of iTOO and a benchmark for the specialty categories iTOO underwrites.
• Beazley: Global specialty insurer strong in cyber, professional, and specialty liability, the same emerging-risk categories iTOO targets, serving as an international category benchmark.
• Hiscox: Global specialist insurer covering art, professional, and small-business liability with digital distribution, mirroring iTOO's art, professions, and SME product mix.

Regional players

• Lombard Insurance: South African specialist insurer focused on guarantees, bonds, and niche commercial lines through intermediaries, comparable in specialty focus and regional footprint.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Key highlights7 records

Customer concentration

• YouTubeyoutube.com/channel/UCdaqSB6vLxZGYEokpqm3GBw
• Facebookfacebook.com/iTOOexpert
• LinkedInlinkedin.com/company/itoo-special-risks-pty-ltd
• Instagraminstagram.com/itooexpert
• Xx.com/itooexpert

Revenue estimate

Valuation estimate

Number of profiles

Profiles6 records

Subsidiaries3 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 ITOO Special Risks