The Westport Group

What The Westport Group does

The Westport Group (TWG) is a privately held, veteran-operated specialty insurance firm founded in 2006 by Christopher R. Kristian and Gary F. Terry, headquartered in Braintree, Massachusetts. The company manufactures and distributes a proprietary High-limit Long-term Disability (High-limit LTD) insurance product as a Lloyd's of London Coverholder, with the authority to quote and bind business on behalf of Lloyd's syndicates. TWG originated the first guaranteed-issue, multi-life, high-limit disability policy ever offered for sale by Lloyd's of London, and today holds the largest book of business in the Lloyd's High-limit disability marketplace. The product fills an income-protection gap left by traditional Group LTD and Individual Disability Insurance (IDI), which cap monthly benefits at levels far below the total compensation of high-income partners and executives.

TWG's core offering is a fully customizable disability policy that layers on top of existing Group LTD and IDI coverage, covering base salary, cash bonus, commissions, K-1 income, and future equity grants (RSUs and PSUs) up to 60% of total annual compensation, with benefits extending to retirement age. The firm targets highly compensated law firm partners (notably the AMLaw 100 segment, where TWG is the dominant provider), corporate executives at publicly traded and private companies, major consulting firm partners, and international managing directors. The product requires a minimum of 10 eligible lives, with average annual premium per case of approximately $1.35M and the largest case exceeding 1,000 lives. TWG also offers an international variant with multi-currency benefit illustration and premium support, addressing populations where IDI cannot be written.

TWG's go-to-market is exclusively enterprise field sales delivered through direct engagement with corporate clients, law firm partnerships, and benefit consultants and insurance brokers. The company supports advisors throughout the sales cycle, with higher closing rates observed when TWG representatives participate directly in client presentations. A proprietary online enrollment and administration system — SOC 2 Type 2, ISO 27001, and GDPR compliant — provides real-time tracking and bespoke plan configuration for each client. White-glove claims support is provided by the same team from sale through claim. TWG has been recognized on the Inc. 5000 list of America's fastest-growing private companies for five consecutive years and ranked #25 on the Boston Business Journal Fast 50 for three consecutive years.

Name

The Westport Group

Legal name

The Westport Group

Website

https://westportgp.com

Company type

Private

Founded year

2006

Operating status

Operating

Headcount range

11–50 employees

Short description

The Westport Group is a Lloyd's of London Coverholder that manufactures and distributes a proprietary High-limit Long-term Disability insurance product, filling the income-protection gap for highly compensated law firm partners, corporate executives, and consulting firm partners whose compensation exceeds traditional Group LTD and IDI benefit caps.

Ownership category

akta.pro rank

Product category

Specialty Disability Insurance

NAICS

Insurance Carriers and Related Activities (524), Insurance Agencies and Brokerages (524210)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Group Disability Income Insurance (Employer-Sponsored) (FSAIAIAB)

akta.pro secondary industries

Key Person Disability Insurance (FSAIAIAK), Disability Buy-Sell / Business Continuation Insurance (FSAIAIAL)

Keywords

• High-limit disability insurance
• Multi-life insurance programs
• Executive income protection
• Lloyd's coverholder services
• Specialty disability coverage

Headquarters

HQ city

Braintree

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, Supply Chain

Revenue model

1. High-limit LTD Insurance Premiums: TWG generates revenue through insurance premiums collected on their proprietary High-limit Long-term Disability insurance products, underwritten by Lloyd's of London. As a Lloyd's Coverholder, TWG has the authority to quote and bind business on behalf of Lloyd's syndicates. Average annual premium at case level is approximately $1.35M.

Pricing tiers

Go-to-market motion1 record

Distribution channels2 records

Marketing channels5 records

Core offering

The Westport Group is a Lloyd's of London Coverholder that manufactures and distributes proprietary High-limit Long-term Disability (High-limit LTD) insurance products. These are guaranteed-issue, multi-life policies designed for highly compensated professionals whose income (typically $700,000 to $8M+) exceeds the benefit caps of traditional Group LTD and Individual Disability Insurance, covering base salary, bonuses, commissions, and future equity grants (RSUs/PSUs) up to 60% of total compensation. TWG delivers these products through a consultative enterprise sales model supplemented by a proprietary online enrollment and administration platform.

Product overview

The Westport Group (TWG) operates as a specialized insurance company offering a unified High-limit Long-term Disability (High-limit LTD) product platform, rather than a modular software system. The core offering is the proprietary High-limit LTD policy, which was the first guaranteed-issue, multi-life, high-limit disability insurance policy ever offered at Lloyd's of London. This flagship product is complemented by specialized variants for partnerships (law firms, consulting, accounting) and corporations (publicly traded and private), all built on the same proprietary platform. TWG also offers proprietary enrollment and claims support services as integral components of their insurance delivery. As a Lloyd's of London Coverholder, TWG manufactures and distributes their policies, distinguishing themselves through customizable plan designs that competitors cannot replicate.

Differentiator

Problem solved

Functional benefit

Products and services

• High-limit Long-term Disability (High-limit LTD) TWG's flagship proprietary disability income protection product specifically designed for high-income earners whose compensation exceeds benefit limitations of Group LTD and IDI policies. The guaranteed-issue, multi-life policy protects salary, bonuses, commissions, and equity compensation (including future RSU/PSU grants) for partners, corporate executives, and highly compensated individuals, with benefits up to 60% of total annual compensation payable to retirement age.
• Multi-life Guaranteed-issue High-limit LTD Program A first-of-its-kind multi-life, guaranteed-issue program designed specifically for partnerships and corporations, with no medical underwriting required. The program seamlessly layers on top of existing Group Long-term Disability (GLTD) and Individual Disability Insurance (IDI) coverage and is offered through direct enterprise field sales with a minimum of 10 eligible lives per case.
• High-limit LTD for Partnerships Specialized High-limit LTD coverage for partners in law, consulting, and accounting firms, addressing the income protection gap above traditional GLTD/IDI caps. Plans provide over $100,000 of monthly benefit payable to Retirement Age. TWG is the dominant provider in the AMLaw 100 segment and serves many consulting firms.
• High-limit LTD for Corporations Coverage designed for publicly traded and private corporations to protect executive compensation packages including bonuses, commissions, long-term incentive plans, and equity grants (RSUs/PSUs). Plans provide over $100,000 of additional monthly benefit payable to Retirement Age, layering on top of existing Group LTD and IDI.

Quantifiable outcome

• 93% average participation rate across TWG's book of business
• +3 more outcomes

Named customers5 records

Segments3 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

One partnership is on record.

• Lloyd's of LondoncoreStrategic or Co-development PartnerTWG is a Lloyd's of London Coverholder — meaning they have the authority to quote and bind business on behalf of Lloyd's underwriters. Lloyd's provides the financial backing and capacity for TWG's High-limit LTD products, enabling coverage of higher income levels than traditional U.S. group DI products. Lloyd's maintains an A+ rating (S&P) and A rating (A.M. Best). This partnership dates back over a decade when TWG sought out Lloyd's after U.S. markets failed to meet the needs of highly compensated professionals.

Scale indicators9 records

Recent moves6 records

Expansion highlights6 records

Emerging players

• Hiscox: Lloyd's-linked specialty insurer with U.S. specialty personal and commercial lines. Operates within the same Lloyd's ecosystem as TWG and is a potential competitor or capacity partner in specialty disability underwriting.

Broad incumbents

• MetLife: Diversified insurer with a large group disability business. Represents the broad incumbent competitive set in group LTD with capacity to enter or expand in the high-limit executive segment that TWG dominates.
• Lincoln Financial Group: Group benefits carrier with disability insurance and executive benefit offerings. Operates in the same broker-distributed employer-sponsored disability market as TWG.
• Unum Group: Largest U.S. disability insurer offering group long-term disability and supplemental executive disability products. Competes with TWG on the employer-sponsored group LTD layer that TWG's High-limit product sits on top of.
• Berkshire Hathaway Specialty Insurance: Specialty insurer with executive lines products including key person and executive disability coverages. Represents a broader specialty carrier competitor with capacity to underwrite high-limit disability risks at scale.
• Principal Financial Group: Large group benefits carrier with significant disability insurance revenue. Competes for the same employer-sponsored disability wallet that TWG accesses through broker and consultant relationships.

Direct peers

• The Standard: Specialty group disability and life insurer with strong employer-sponsored LTD market share. Competes for the same group LTD and supplemental executive disability accounts that TWG serves in the law firm and corporate segments.
• Northwestern Mutual: Major provider of individual disability income insurance for high-income professionals. Competes with TWG for high-earning professionals' disability coverage needs, particularly where IDI products overlap with TWG's High-limit LTD.
• MassMutual: Leading provider of individual disability income insurance and group disability products. Directly comparable to TWG's high-limit LTD product which is designed to layer on top of IDI coverage.
• Guardian Life Insurance: Major group disability and supplemental executive benefits carrier with a Supplemental Program Operations business unit. Multiple TWG executives previously held senior roles at Guardian, indicating direct competitive overlap in the high-limit executive disability space.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

• LinkedInlinkedin.com/company/the-westport-group-llc
• Xx.com/thewestportgp

Compliance3 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles6 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 The Westport Group