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Top Insurance Companies in Boston, MA (119)

MassMutual
Big Data • Fintech • Information Technology • Insurance • Financial Services
We help people secure their future and protect the ones they love.

Since 1851, MassMutual’s commitment has always been to help people protect their families, support their communities, and help one another. This is why we want to inspire people to Live Mutual. We’re people helping people. Together, we’re stronger.

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MassMutual

MassMutual's Top Stability & Growth Strengths

Strong Revenue Growth: Sales are reported to have risen from about $39 billion (2023) to more than $43 billion (2025), with 2024–2025 gains attributed to institutional solutions, whole life, and annuities.

Profitability: Operating earnings are characterized as increasing from $2.8 billion in 2024 to nearly $3.9 billion in 2025, a company‑record level.

Investor Backing & Capital Strength: Capital levels are described as strong, with total adjusted capital at $34.4 billion in 2025 and high financial‑strength ratings maintained across major agencies.

Simply Business
Fintech • Information Technology • Insurance • Software
Insuring small businesses, enabling big dreams.

Simply Business is the leading digital insurance marketplace dedicated to the success of small businesses. Our mission is to take the hassle out of buying insurance by offering simplicity, choice, and value to business owners. We connect our customers with top-rated insurers and policy recommendations tailored to their specific business needs and budget. We have nearly 20 years of experience supporting...

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Simply Business

Simply Business's Top Stability & Growth Strengths

Strong Revenue Growth: UK company filings indicate revenue rose from about £169.4m in 2023 to £197.0m in 2024, evidencing clear double-digit growth. Parent-company reporting in 2025 also attributed an increase in its ‘Other revenues’ to growth in Simply Business.

Profitability: Operating profit reportedly increased from roughly £24.2m to £45.9m in 2024, rising far faster than revenue. This points to improving margins and efficiency alongside scale.

Market Expansion: The business surpassed one million customers globally in 2024 and later reached one million in the UK, with continued activity in the U.S. and new partnerships and office investments. These milestones suggest ongoing expansion of reach and channels.

Hi Marley
Artificial Intelligence • Cloud • Insurance • Software • Database • Conversational AI • Generative AI
Boston
140 Employees
53 Benefits Hiring Now
Hi Marley is the intelligent conversational platform built for P&C insurance.

Hi Marley is the Intelligent Communication Platform for P&C Insurance. Founded in 2017 and headquartered in Boston, Hi Marley helps carriers deliver better insurance experiences through communication that is simple, connected, and built for the way P&C teams work. Trusted by more than 130 carriers, including 4 of the top 10, Hi Marley connects carriers and the insurance ecosystem in...

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Hi Marley

Hi Marley's Top Stability & Growth Strengths

Strong Revenue Growth: Evidence indicates revenue grew rapidly over the period recognized by Deloitte’s 2025 Technology Fast 500, with earlier multi‑year gains also cited. Consecutive Fast 500 placements suggest sustained top‑line momentum.

Market Expansion: The company reports 130+ customers, including 13 of the top 30 P&C carriers, and moved to a much larger Boston headquarters. Customer counts have increased markedly since earlier periods, indicating broader market reach.

Product Line Growth: Materials describe expansion beyond claims into policyholder service and the launch of Unite to connect carriers with service providers. These additions broaden use cases and deepen penetration within carriers.

Gradient AI
Artificial Intelligence • Insurance • Machine Learning • Software • Analytics
Boston
130 Employees
87 Benefits Hiring Now
Powering a Better Return on Risk

Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry’s largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has...

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Gradient AI

Gradient AI's Top Stability & Growth Strengths

Investor Backing & Capital Strength: Significant financing includes a $56.1M Series C in 2024 and additional growth-capital funding from CIBC Innovation Banking in March 2026, signaling continued investor confidence and runway. Company communications indicate these funds are directed toward product development, R&D, customer success, and sales.

Product Line Growth: Recent launches and expansions span Renewal Analytics, workers’ compensation capabilities (including a claims-triage solution), and a major expansion of the Group Health analytics platform, alongside an integrated Risk Management Life Cycle solution. This pattern points to broadening coverage across underwriting, renewals, and claims.

Customer Loyalty & Retention: Current materials highlight hundreds of enterprise deployments with very high client retention, paired with ongoing wins and deployments in 2025–26 (e.g., Community Health Options, Evolution Risk Partners, and continued 2026 additions). These signals suggest a sticky and expanding customer base.

Agero
Automotive • Big Data • Insurance • Software • Transportation
Medford
1,600 Employees
65 Benefits Hiring Now
As the B2B industry leader, we are reimagining how to deliver support to drivers at ever step of vehicle ownership.

Agero is a leading provider of driver assistance, accident management, consumer affairs support and connected vehicle services for stakeholders across the automotive industry, including the world’s largest automakers, auto retailers, insurers, rideshare providers and other brands. As the driving force behind mobility support throughout all points in the vehicle ownership journey - from purchase to maintenance and breakdown to resell or...

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Agero

Agero's Top Stability & Growth Strengths

Market Expansion: The company reports a larger operating footprint—supporting around 150 million vehicles and approximately 14 million annual service events—and has expanded via strategic moves such as the Urgently acquisition. New and renewed programs with major automotive and insurance brands further indicate broader market reach.

Strong Market Position & Advantage: Industry recognition such as Frost & Sullivan’s North American Company of the Year honors portrays a commanding position in digitalized roadside assistance. Claims of extensive OEM integrations and deep insurer penetration reinforce an entrenched competitive stance.

Innovation-Driven Growth: Continued investment in software-enabled dispatch platforms, automation, and connected-vehicle tools is emphasized as central to the strategy. Rapid uptake of Crash Response and other digital workflows points to technology-enabled scaling.

Liberty Mutual Insurance
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Join us, and pursue your tomorrow, today.

Liberty Mutual Insurance exists to help people embrace today and confidently pursue tomorrow. A Fortune 100 company and global leader in property and casualty insurance, we’ve spent over a century creating innovative products, services and technologies to meet the world’s ever-changing needs and make a difference for our customers and communities.

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Liberty Mutual Insurance

Liberty Mutual Insurance's Top Stability & Growth Strengths

Profitability: Net income rose to $6.79B in 2025 from $4.38B in 2024. The combined ratio improved materially (e.g., S&P-adjusted 89.7% in 2025 and high-80s in early 2026), indicating stronger underwriting performance.

Investor Backing & Capital Strength: Shareholders’ equity increased from about $22.2B in 2022 to $39.9B at year-end 2025 and exceeded $44B by mid-2026. External ratings actions (AM Best A affirmation in Sept 2025; S&P upgrade to A+ in July 2026) underscore improved capitalization.

Resilient & Sustainable Growth: S&P describes deliberate portfolio reshaping and expects 2–3% annual premium growth during 2026–2028. Management emphasizes disciplined, selective expansion following underwriting improvements, prioritizing durable returns over sheer volume.

Leader Bank
Fintech • Insurance • Payments • Social Impact • Financial Services
Arlington
420 Employees
41 Benefits Hiring Now
Leader Bank is defined by our exemplary products and client services as well as our innovative spirit.

Founded in 2002, Leader Bank is a Massachusetts-based entrepreneurial financial institution that approaches banking differently. The core tenets of Leader Bank include client services, exemplary products, and innovation to meet the needs of its clients. Leader Bank’s best-in-class staff has been at the forefront of supporting the bank’s rapid growth and client-oriented solutions, as the bank has continued to expand...

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Leader Bank

Leader Bank's Top Stability & Growth Strengths

Resilient & Sustainable Growth: Assets and loans have increased over multiple years, with total assets moving from $4.434B in 2023 to $5.032B in 2025 and further increases reported into 2026. This trajectory is supported by expanding residential lending volumes and a broadened footprint.

Profitability: Net income rose from $17.0M in 2023 to $23.7M in 2024, indicating stronger earnings performance. This improvement accompanied portfolio growth and higher lending production in 2024.

Market Expansion: Physical presence is growing with three new Massachusetts branches announced for 2026 (Boston Seaport, Andover, Falmouth). Reach is further extended by additions like a nationwide SBA lending group and a West Coast deposit team.

Openly
Insurance
Fully Remote
350 Employees
51 Benefits Hiring Now
Challenging the industry status quo while serving Agents & Policyholders by using data, technology, and expertise.

Openly is proud to offer innovative, comprehensive homeowners insurance, wrapped in modern convenience. We arm agents with the tools necessary to serve up a world class customer experience.

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Openly

Openly's Top Stability & Growth Strengths

Strong Revenue Growth: Written premium increased from 2023 to 2024, and early 2026 results were reported higher year over year, indicating ongoing top-line momentum. Industry coverage cites hundreds of millions in annual premium, underscoring scale.

Market Expansion: The footprint reached 24 states after new launches in 2024, with additional states planned. Agent distribution spans tens of thousands of independent agents, signaling broader reach.

Investor Backing & Capital Strength: Significant financing was secured in 2025 and again in 2026, with participation from established investors. A deepened long-term reinsurance relationship with Allianz Re further supports capacity for growth.

iptiQ
Big Data • Information Technology • Insurance • Marketing Tech
Cambridge
150 Employees
22 Benefits

iptiQ is a start-up unit, established within SwissRe to provide life insurance protection solutions directly to consumers. We deliver the coordination, infrastructure and competences that are key to driving forward this new business. Our mission is to reduce the protection gap by simplifying life insurance and making it more accessible to people.

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iptiQ
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Marsh & McLennan Agency
Insurance • Professional Services • Consulting • Financial Services
8 Offices
15,000 Employees
29 Benefits

Marsh McLennan Agency (MMA) is a leading insurance brokerage and risk management firm providing business insurance, employee health & benefits, retirement solutions, and private client insurance services.

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Marsh & McLennan Agency
Wellabe
Insurance
3 Offices
412 Employees
18 Benefits

Our company was founded by Watson Powell in 1929 as American Republic Insurance Company. From the beginning with 200 charter policies, our company was dedicated to providing personal insurance services at an affordable price. Through sound fiscal responsibility, our young company survived the Great Depression, which came just six months later. By 1945, our company moved beyond our Iowa borders...

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Wellabe
Energetic Insurance
Fintech • Greentech • Insurance • Energy
Cambridge
12 Employees
Unlocking solar financing for unrated or below investment grade organizations.

Energetic Insurance is a Managing General Underwriter (MGU) with a novel, data-driven approach to develop new risk management products to unlock exponential growth in the renewable energy industry. For solar industry participants who want to do more projects and deploy more capital, EneRate Credit Cover™ unlocks solar project financing for the unrated and below investment grade counterparties by covering payment...

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Energetic Insurance
Rockland Trust Company
Insurance • Financial Services
12 Offices

Rockland Trust is a full-service commercial bank offering a wide range of banking, investment, and insurance services to businesses and individuals.

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Rockland Trust Company

Rockland Trust Company's Top Stability & Growth Strengths

Market Expansion: The company materially broadened its footprint via the 2025 Enterprise Bancorp acquisition, complemented by a new Marlborough branch and expanded facilities and headquarters plans that deepen its presence across Massachusetts and southern New Hampshire. Integration completed in October 2025 and continued physical investments indicate a larger, denser regional network.

Profitability: Reported results showed improving earnings momentum into late 2025 and Q1 2026, with management linking better performance to progress on the Enterprise integration. A dividend increase further signals confidence in post‑integration earnings power.

Strong Brand Reputation: Recognition such as Forbes’ No. 1 Bank in Massachusetts (2024), top‑tier regional customer‑satisfaction placements, and multiple Coalition Greenwich awards reflect strong standing with retail and business clients. Consistent accolades reinforce a leadership perception within Massachusetts and New England.

Zurich North America
28 Offices
56,000 Employees
33 Benefits
Zurich has over 150 years of experience managing risk and supporting resilience for customers around the world.

Founded in Switzerland in 1872, Zurich expanded to North America in 1912 to become a leading provider of commercial property-casualty insurance solutions and services in the U.S. and Canada. Today, we serve a diverse set of industries including automotive, agriculture, construction, manufacturing, technology and numerous others. Our customers include 90% of the Fortune 500® as well as a diverse array...

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Zurich North America

Zurich North America's Top Stability & Growth Strengths

Strong Market Position & Advantage: Zurich North America is positioned in the top tier of U.S. commercial lines by direct premiums written and is repeatedly framed as a leading commercial P&C provider. Multinational programs and complex-risk specialties are highlighted as differentiators that keep it on shortlists for large and global accounts.

Profitability: Recent disclosures describe record P&C operating results at the group level with North America P&C profit increasing year over year and the combined ratio improving. Portfolio actions are depicted as underwriting discipline that prioritizes margin quality rather than pure premium volume.

Strong Hiring & Retention: The U.S. Middle Market business is described as experiencing multiple consecutive years of double-digit growth alongside plans to add over 100 underwriting roles to expand geographic reach. Organizational changes such as creating a dedicated Specialties unit are presented as capacity-building to support further growth.

BeneSys Inc
Insurance
19 Offices
505 Employees
21 Benefits

BeneSys is a team of dedicated Taft-Hartley Trust Fund Specialists. BeneSys understands the nuances of Taft-Hartley benefit plans. We are experienced and accustomed to programming and administering plans that have unusual benefit plan parameters. Our software system Benefitdriven.com is dedicated to providing our clients and their plan participants with the most efficient tools for self-administering trust fund accounts. Our benefits...

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BeneSys Inc
Videa
Artificial Intelligence • Healthtech • Insurance • Software
2 Offices
110 Employees
3 Benefits Hiring Now

VideaHealth is transforming Dentistry by combining advanced AI of x-ray images with integrated software that dramatically improves diagnoses and streamlines insurance claims processing. Patients get better recommendations, dentists learn faster, and insurers reduce fraud, waste and abuse in real time. Our AI factory continuously expands the range of conditions we can detect, including those that affect broader medical risks. Our...

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Videa

Videa's Top Stability & Growth Strengths

Strong Market Position & Advantage: Adoption at scale across large DSOs and tens of thousands of clinicians, along with multiple FDA 510(k) clearances, positions the company in the leading cohort of dental AI platforms. Enterprise-wide rollouts (e.g., Aspen, Heartland, Great Expressions) reinforce its credibility and reach.

Strategic Partnerships: Integration with Henry Schein One’s Dentrix platforms embeds the technology into widely used practice-management workflows, enhancing distribution and usage. Public DSO partnerships and network-wide deployments expand access across hundreds to thousands of practices.

Product Line Growth: Expansion beyond radiographic AI into voice tools and Ambient Intelligence indicates a broadening platform across clinical, operational, and revenue workflows. The 2025–2026 launch cadence and rebrand signal momentum in adjacent product categories.

Boston Omaha
AdTech • Insurance • Real Estate
Boston
6 Employees

Boston Omaha operate three separate lines of business: outdoor billboards, surety insurance and related brokerage activities.

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Boston Omaha
OnSource Online
Insurance • Mobile • Software • Analytics
Braintree
65 Employees

Headquartered in Braintree, MA, OnSource enables insurance companies to get fast, fair and efficient claims and underwriting photo inspections through intuitive smartphone apps and a mobile website that take the guesswork out of insurance photography. Policyholders and claimants can use self-inspection apps, Instant Inspection’s chat website, or an extensive network of 10's of thousands of photo field inspectors and quality...

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OnSource Online
Winged Keel Group
Insurance • Analytics • Financial Services
5 Offices
130 Employees
37 Benefits Hiring Now
New York • San Francisco • Boston • Richmond • Washington, D.C. • Houston • Atlanta • Denver • St. Louis • Minneapolis

Founded as an independent life insurance brokerage firm in 1989, Winged Keel Group specializes in the structuring and administration of large block life insurance portfolios for sophisticated business owners, private investors, executives, and ultra-affluent families. Since inception, we have helped clients acquire more than $95 billion of coverage using a variety of sophisticated planning and product strategies, which help our...

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Winged Keel Group
XDimensional Technologies, Inc.
Insurance • Software
Boston
67 Employees

For over two decades, XDimensional Technologies has been serving the insurance industry with innovative solutions that make business more efficient and productive throughout the insurance value chain. We work closely with our customers and partners to understand their evolving needs and issues, and then map those understandings into solutions that improve business results. And we assure our solutions are flexible...

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XDimensional Technologies, Inc.

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