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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.

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.

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.

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.

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.

FM Global
Insurance
25 Offices
5,675 Employees
43 Benefits

FM Global is one of the world’s largest commercial property insurers. For nearly 200 years, the world’s leading businesses have worked with FM Global to develop robust property insurance and engineering solutions that build resilience into every corner of their operations. These solutions protect against fire, natural disasters and other types of property risk. We provide more than one-third of...

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FM Global

FM Global's Top Stability & Growth Strengths

Strong Market Position & Advantage: FM is positioned as a leader in large-commercial property insurance, particularly within the Highly Protected Risk (HPR) niche, supported by a differentiated engineering-driven loss-prevention model. Its penetration among large enterprises is reinforced by references to serving a substantial share of Fortune 500/Fortune 1000 companies.

Investor Backing & Capital Strength: The company is described as having strong capital and balance-sheet strength, with repeated references to very high policyholder surplus and top-tier financial strength ratings from multiple agencies. Large membership credits returned to clients are presented as enabled by strong financial performance and capitalization.

Resilient & Sustainable Growth: The data cites multi-year increases in premiums and surplus, alongside continued investments in brand, footprint, and capacity, indicating growth that is supported by profitability and capital accumulation. Expansion moves (e.g., offices and higher limits for specific segments) are portrayed as strengthening long-term growth momentum.

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Shift Technology
Artificial Intelligence • Information Technology • Insurance • Machine Learning • Software • Automation
5 Offices
559 Employees
27 Benefits Hiring Now

Shift Technology delivers AI decisioning solutions to benefit the global insurance industry and its customers. Our products enable insurers to automate and optimize decisions from underwriting to claims, resulting in superior customer experiences, increased operational efficiency, and reduced costs. The future of insurance starts with Decisions Made Better. Learn more at www.shift-technology.com

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Shift Technology
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
PMA Companies
Insurance
19 Offices
1,511 Employees
27 Benefits Hiring Now

PMA Companies provides risk management solutions and services, specializing in workers’ compensation and offering property & casualty insurance, in the United States. Headquartered in Blue Bell, PA, PMA Companies is a member of Old Republic Companies. Old Republic International Corporation (NYSE: ORI) is one of the nation’s 50 largest publicly held insurance organizations. PMA Companies includes: PMA Insurance Group, specializing in workers’...

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PMA Companies

PMA Companies's Top Stability & Growth Strengths

Investor Backing & Capital Strength: Being part of a Fortune 500 parent with long operating history underscores capital stability and financial resilience. Strong group support enables confidence to pursue larger accounts and long-term underwriting commitments.

Market Expansion: Recent leadership appointments, targeted regional growth efforts, and new offerings like a group captive indicate active expansion. Employee growth further signals investment in capacity and capabilities.

Customer Loyalty & Retention: High retention among core insurance and TPA clients suggests durable relationships and recurring revenue resilience. This stickiness supports steadier performance through competitive cycles.

Assured Allies
Insurance
3 Offices
75 Employees

Prevent what you can. Prepare for what you can’t. That's the simple yet powerful philosophy that drives us. There are proven tools and techniques that are available - right now - to help millions age successfully and prevent what we used to think of as inevitable. But many people don't know about them, or how to apply them. That's the gap...

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Assured Allies
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
Global Atlantic Financial Group
11 Offices
1,140 Employees
24 Benefits

Global Atlantic Financial Group, through its subsidiaries, offers a broad range of retirement, life and reinsurance products designed to help our customers address financial challenges with confidence. A variety of options help Americans customize a strategy to fulfill their protection, accumulation, income, wealth transfer and end-of-life needs. In addition, Global Atlantic offers custom solutions and responsive service for the capital,...

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Global Atlantic Financial Group

Global Atlantic Financial Group's Top Stability & Growth Strengths

Resilient & Sustainable Growth: Invested assets are described as expanding at a double-digit pace over a multi-year period, supported by core insurance activity. Large reinsurance transactions and continued inflows are presented as adding scale and reinforcing a sustained growth trajectory through 2025–2026.

Investor Backing & Capital Strength: Full ownership by KKR via a multi-billion-dollar purchase is presented as strengthening alignment, integration, and access to capital resources. A-category rating actions/affirmations and references to strong capital levels are positioned as supportive of resilience for policyholders and counterparties.

Strong Market Position & Advantage: The company is positioned as a top-tier participant in life/annuity block reinsurance and a recurring top seller in selected retail annuity categories. Marquee block deals and repeated product recognition are presented as reinforcing competitive standing in its core lanes.

American Income Life Insurance Company
43 Offices
8,078 Employees
19 Benefits

American Income Life is a major provider of supplemental insurance benefits to working families through relationships established with labor unions, credit unions, and associations. The Company was founded with just $25,000 in borrowed capital more than 50 years ago by entrepreneur and philanthropist Bernard Rapoport. American Income Life is licensed in 49 states, the District of Columbia, Canada, and is registered...

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American Income Life Insurance Company
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
Brown & Brown Insurance
35 Offices
2,391 Employees
36 Benefits Hiring Now

Brown & Brown Insurance provides risk management solutions to help protect what our customers value most. Our four business segments offer insurance products and services to businesses and individuals. Our culture is built on integrity, innovation, superior capabilities, and discipline. We view insurance differently and use our experience, carrier relationships, and principled customer focus to deliver first-class service and solutions....

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Brown & Brown Insurance

Brown & Brown Insurance's Top Stability & Growth Strengths

Strong Market Position & Advantage: Industry rankings place Brown & Brown as a top‑10 global and top‑six U.S. broker, underscoring a first‑tier competitive position. S&P 500 inclusion and an expanded specialty platform following Accession/One80 further reinforce market standing.

Strong Revenue Growth: Reported FY 2025 revenue reached about $5.9B with roughly 22.8% growth, and Q1 2026 revenue was about $1.9B, up 35.4% year over year. Results also reflected higher adjusted earnings alongside the larger operating footprint.

Market Expansion: The 2025 Accession (Risk Strategies/One80) acquisition materially broadened wholesale and programs capabilities, creating a larger specialty distribution footprint. Subsequent reorganization (e.g., Arrowhead Intermediaries integration) deepened reach across specialty business.

Coventry
Insurance
29 Offices
464 Employees
4 Benefits

At Coventry, we look at things from an entirely different perspective. It’s what has enabled us to find new value. And in the process, ignite a transformation in the financial services industry. It started out as a way to help bring value to our clients. It ended up challenging the conventions of our industry, redefining life insurance and accomplishing what...

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Coventry
Homesite Insurance
4 Offices
1,453 Employees
30 Benefits

Homesite. We've got you covered. Founded in 1997, Homesite insurance was the first company to enable customers to purchase insurance directly online, during a single visit. Since then, we’ve continued to innovate at the pace of our customers and their changing expectations. One thing that’s stayed the same since our founding: our commitment to our customers and partners. We now offer...

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Homesite Insurance

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