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The 41 largest Insurance companies in Connecticut

Tamtam tracks 41 Insurance companies headquartered in Connecticut. This list ranks all of them by number of employees on LinkedIn, led by HealthPlanOne, HSB - Hartford Steam Boiler and Gen Re. Their median headcount is 157. Half of them were founded in 1988 or later. The most common headquarters are Stamford (8), Hartford (7) and Shelton (4).

馃嚭馃嚫 Connecticut41 companiesUpdated Oct 24, 2026
#CompanyIndustryHeadquarters EmployeesFounded
1
HealthPlanOnehpone.com

A company specializing in helping people make healthcare choices, particularly focused on Medicare, with personalized service and effective lead generation strategies since 2006

Insurance 馃嚭馃嚫 Shelton 3,918 2006
2
HSB - Hartford Steam Boilermunichre.com

Engineering and technical risk insurance provider offering equipment breakdown coverage, specialty solutions, inspection services, and consulting to optimize client operational reliability and efficiency.

Insurance 馃嚭馃嚫 Hartford 2,599 1866
3
Gen Regenre.com

Provides treaty and facultative reinsurance services globally with expert underwriting, actuarial, and claims support tailored to client needs.

Insurance 馃嚭馃嚫 Stamford 1,861 1921
4
Knights of Columbus Insurancekofc.org

A Catholic fraternal organization providing life insurance and financial products Over $155 billion and 691 million volunteer hours donated to charitable causes

Insurance 馃嚭馃嚫 New Haven 795 1882
5
Nassau Financial Groupnfg.com

Insurance company offering retirement-focused products including savings protection, guaranteed income, and healthcare cost coverage with dedicated customer service.

Insurance 馃嚭馃嚫 Hartford 695 2015
6
HCSGhcsg.net

A technology company specializing in cost containment systems and services for healthcare insurance organizations, using innovative technology to optimize programs

Insurance 馃嚭馃嚫 Shelton 613 2002
7
OdysseyReodysseyre.com

Provides diverse property, casualty, and specialty reinsurance solutions globally through multiple offices, part of a major financial holdings group.

Insurance 馃嚭馃嚫 Stamford 571 n/a
8
Talcott Financial Grouptalcott.com

A life insurance and annuity company with a focus on client needs and innovative solutions, backed by a leading global investment firm

Insurance 馃嚭馃嚫 Hartford 506 2018
9
Futurity Firstfuturityfirst.com

A nationwide network of financial experts specializing in wealth management and income planning for seniors, pre-retirees, families, and businesses, offering diverse product solutions and support

Insurance 馃嚭馃嚫 Middletown 425 2008
10
ConnectiCareconnecticare.com

A leading health plan in Connecticut providing a range of products and services, including free health classes, support, and resources for members and non-members

Insurance 馃嚭馃嚫 Farmington 409 1981
11
Navigators, a Brand of The Hartfordthehartford.com

Market-leading provider of E&S solutions through valued wholesale brokers, offering wide-ranging, flexible coverage, high-risk tolerance, and creative solutions for non-traditional risks

Insurance 馃嚭馃嚫 Hartford 393 1974
12
CATICcatic.com

A company licensed in multiple states, underwriting member of ALTA, offering title insurance through independent agent network Visit wwwCATICcom for more information

Insurance 馃嚭馃嚫 Rocky Hill 386 1966
13
IFG Companiesifgcompanies.com

An established insurance group offering property-casualty coverage through two divisions, Bind and Brokerage, with multiple business units and affiliated insurers

Insurance 馃嚭馃嚫 Hartford 361 1985
14
Smith Brothers Insurance, LLC.smithbrothersusa.com

An independently operated insurance broker with over 50 years of experience, providing personalized risk management services to protect assets and achieve goals

Insurance 馃嚭馃嚫 Glastonbury 243 1971
15
GenStar Insurance Services, LLCgeneralstar.com

A leading specialty and surplus lines provider offering stable financial backing, creative underwriting, exceptional customer service, and expertise in challenging risk management scenarios

Insurance 馃嚭馃嚫 Stamford 218 n/a
16
TravelInsured.comtravelinsured.com

A trusted provider of comprehensive travel insurance and assistance services, committed to ensuring travelers embark on journeys with safety and peace of mind

Insurance 馃嚭馃嚫 Glastonbury 183 1994
17
Berkley Re (a Berkley Company)berkleyre.com

Global reinsurance provider offering treaty and facultative reinsurance solutions to insurance companies and self-insured businesses worldwide through local experts in key regions

Insurance 馃嚭馃嚫 Greenwich 183 n/a
18
JMG Insurance Corpjmg.com

The company is an independent insurance agency serving Connecticut, Massachusetts, New York, and New Jersey, offering personalized coverage options with affordable rates and great customer service

Insurance 馃嚭馃嚫 Norwalk 178 1916
19
Wilton Rewiltonre.com

A US life re-insurance company specializing in acquiring in force life insurance and annuities, providing risk capital, and implementing new business strategies

Insurance 馃嚭馃嚫 Norwalk 166 n/a
20
Paragon Insuranceparagoninsgroup.com

Specialty Program Administrator offering stable, unique insurance programs to retail brokers and carrier partners Diversified programs include Workers' Comp, Auto Dealership, and more

Insurance 馃嚭馃嚫 Avon 164 2014
21
RVI Grouprvigroup.com

Specializing in property and casualty insurance, providing residual value insurance products to protect against market value declines in various asset classes

Insurance 馃嚭馃嚫 Stamford 157 1990
22
Arch Re Facultativereinsurance.archgroup.com

Global reinsurance provider offering significant capacity, creative solutions, and superior client service through experienced underwriters, expert underwriting, skilled claims management, and world-class products

Insurance 馃嚭馃嚫 Farmington 120 n/a
23
ebmgetebm.com

ebm offers employee benefits solutions through industry-leading technology platforms and administrative services for consultants and HR, prioritizing client success

Insurance 馃嚭馃嚫 North Haven 66 2013
24
Globex International Groupglobexintl.com

International risk management, insurance, and employee benefits consultancy firm enabling global insurance organizations to offer products worldwide

Insurance 馃嚭馃嚫 Fairfield 62 1993
25
Highstreet Insurance & Financial Services, Bristol, CTmyhighstreet.com

Diversified insurance and financial services organization providing tailored solutions for individual and commercial clients, including home and auto insurance, employee benefits, and financial services

Insurance 馃嚭馃嚫 Bristol 53 1920
26
Northfield Excess & Surplus Linesnorthfieldins.com

Specialty insurer with 40+ years of experience in non-admitted marketplace, offering hard-to-place risk coverages through national network of wholesale agents and brokers

Insurance 馃嚭馃嚫 Hartford 46 n/a
27
Berkley Re America (a Berkley Company)berkleyre.com

Specializing in reinsurance on Treaty and Facultative basis, offering custom solutions in property, casualty, professional liability, and workers' comp Dedicated to strong client relationships

Insurance 馃嚭馃嚫 Stamford 36 n/a
28
DiMatteo Insurancecrossagency.com

A family-owned business offering a wide range of insurance, financial, and tax services with a focus on exceptional customer service They also support various charitable organizations

Insurance 馃嚭馃嚫 Shelton 34 1960
29
Genesis Management and Insurance Services, LLCgenesisinsurance.com

Premier alternative risk insurance provider offering innovative solutions for public entity, commercial, and captive clients for over 30 years Owned by General Reinsurance Corporation

Insurance 馃嚭馃嚫 Stamford 26 1988
30
Pierson & Smith, Inc.piersonandsmith.com

Independent insurance firm specializing in brokerage, consulting, and third party administration for corporate and individual clients, offering unique and tailored risk management solutions

Insurance 馃嚭馃嚫 Norwalk 19 1946
31
The Travelers Companies, Inctravelers.com

A Georgia-based insurance company providing insurance services from their headquarters in Augusta, United States

Insurance 馃嚭馃嚫 Hartford 19 1925
32
D.W. Van Dyke & Co.dwvd.com

A privately held reinsurance intermediary designing risk transfer programs and providing solutions with experienced insurance and reinsurance underwriters

Insurance 馃嚭馃嚫 Shelton 16 1978
33
Cultural Insurance Services International (CISI)culturalinsurance.com

Specializing in insurance coverage for international education and cultural exchange, offering tailored individual and group plans with 24/7 crisis management support worldwide

Insurance 馃嚭馃嚫 Stamford 16 1996
34
Daly Insurance Brokerage Services, LLCdalybrokerage.com

A brokerage firm focused on providing superior service to protect lives against risk, working closely with brokers as a platform and resource

Insurance 馃嚭馃嚫 Southington 15 1997
35
Nicholas/Tobin Insurancentins.com

This company offers high-quality insurance products and services to protect clients' families and businesses, with a strong commitment to service and community support

Insurance 馃嚭馃嚫 New Milford 14 1979
36
Beacon Retiree Benefits Group, LLC An Alera Group Companybeaconmedicare.com

The company specializes in providing guidance on Medicare plan options, offering objective advice for informed decisions that best fit individual needs

Insurance 馃嚭馃嚫 Plantsville 11 1994
37
Wentworth-DeAngelis & Kaufman Insurancewdkins.com

A full service insurance brokerage firm offering personalized solutions for individuals, businesses, and non-profit agencies, with a focus on excellent service and client satisfaction

Insurance 馃嚭馃嚫 Farmington 11 1997
38
A&S Insurance, LLCaandsinsurance.com

Specializing in Home and Auto insurance, our agency offers a wide range of policies as well as exceptional customer service Contact us for a free quote today!

Insurance 馃嚭馃嚫 New Haven 8 1993
39
Marcus Insuranceking-insurance.com

Established in 1941, a top insurance agency in Connecticut offering personalized services for Home, Auto, and business needs through partnerships with multiple companies

Insurance 馃嚭馃嚫 Wethersfield 8 1941
40
Berkley Aviation (a Berkley Company)berkley.com

The company offers a variety of insurance and reinsurance products through its operating units Visit the website for more information

Insurance 馃嚭馃嚫 Greenwich 6 2005
41
Berkley Re America. LLCberkleyre.com

Assisting insurance companies and businesses in managing net risk through Treaty and Facultative Reinsurance to mitigate potential losses

Insurance 馃嚭馃嚫 Stamford 2 n/a

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How this list is built

Every company on this list has a Tamtam company profile. The industry is the one the company gives on LinkedIn; categories such as SaaS or fintech are classified by Tamtam's AI from the company's website and LinkedIn page; and the headquarters city must match the company's own address. Companies are ranked by the number of employees on LinkedIn, and the list is refreshed every night. Classifications can be wrong, so treat the list as a starting point rather than an official ranking. Last updated Oct 24, 2026.

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