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Top Insurance Companies in Boston, MA (119)

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.

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.

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.

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 and powered by SMS.

Hi Marley is the first intelligent conversational platform built for P&C insurance and powered by SMS. Designed by insurance professionals, Hi Marley enables lovable, convenient conversations across the entire ecosystem, saving money and time for carriers while building customer loyalty through delightful interactions. Hi Marley's industry-leading collaboration, coaching and analytics capabilities deliver crucial insights that streamline carrier operations while enabling...

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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.

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.

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.

Indico Data
Artificial Intelligence • Enterprise Web • Insurance • Machine Learning
Boston
75 Employees
22 Benefits
Indico Data automates critical workflows for enterprises in document-intensives industries.

Indico Data transforms unstructured data into actionable insights. With the AI and ML-powered Indico Unstructured Data Platform™, enterprises of all sizes can automate, analyze, and apply unstructured data – documents, emails, images, videos and more – to a wide range of enterprise workflows. This enables them to gain rich insight and maximize the value of their existing software investments, including...

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Indico Data
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AIR Worldwide
Insurance • Software
Boston

AIR Worldwide, a Verisk (Nasdaq:VRSK) business, pioneered the catastrophe modeling industry, creating the tools and technologies that changed how people think about risk management.

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AIR Worldwide
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
Measured Analytics and Insurance
Artificial Intelligence • Insurance • Analytics
9 Offices
9 Employees
22 Benefits

Measured builds smarter insurance products, using AI-driven analytics to calculate and cover our clients’ exposure in real-time.

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Measured Analytics and Insurance
Indigo (getindigo.com)
Artificial Intelligence • Insurance
3 Offices
42 Employees
29 Benefits

Indigo leverages artificial intelligence to vastly improve the medical liability insurance industry for brokers and physicians.

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Indigo (getindigo.com)
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.

Accession Risk Management Group
Insurance • Financial Services
2 Offices
5,000 Employees

Accession Risk Management Group is a family of specialty insurance distribution and risk management companies that provides comprehensive risk management advice, insurance and reinsurance placement, employee benefits, and consulting services through its member companies.

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Accession Risk Management Group
Liberty Mutual Canada
Insurance • Financial Services
15 Offices
41 Benefits

Liberty Mutual Canada is the Canadian branch of Liberty Mutual Insurance Company, providing a broad suite of commercial property and casualty insurance products and solutions to mid-size and large Canadian companies.

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Liberty Mutual Canada
Herald
Fintech • Insurance • Financial Services
Boston
104 Employees
Digital Infrastructure for commercial insurance.

Herald builds digital infrastructure for commercial insurance. Quote and bind insurance from multiple carriers using a single API.

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Herald
SIMON from iCapital
Cloud • Fintech • Insurance • Sales
16 Offices
154 Employees
51 Benefits
SIMON was built to simplify. We empower financial professionals to deliver a better tomorrow for their clients.

SIMON works to build transparency around complex, risk-managed and alternative investments by way of a centralized, on-demand digital platform, available to more than 100,000 financial professionals. Our platform simplifies the complexity of the modern investment landscape, with tools that make it easier to navigate and manage a wider range of products. We deliver education, analytics, a marketplace, lifecycle management, and...

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SIMON from iCapital
Amica
Insurance
17 Offices
2,719 Employees
37 Benefits

When you look at Amica, you’ll see we’re different. We’re a mutual company, which means we serve policyholders, not stockholders. Our culture is built on kindness and mutual respect that’s reflected in how we treat our customers and support our people. We offer fair compensation, comprehensive medical coverage, and generous extras like reimbursement for gym fees and student loan repayment...

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Amica

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