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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 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.

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.

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.

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.

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.

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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Guidewire Software
Cloud • Information Technology • Insurance • Software • Analytics
24 Offices
3,400 Employees
34 Benefits Hiring Now
Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently.

Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. ​We combine digital, core, analytics, and AI to deliver our platform as a cloud service. More than 540 insurers, from new ventures to the largest and most complex in the world, run on Guidewire. As a partner to our customers, we continually evolve to enable their success. We...

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Guidewire Software

Guidewire Software's Top Stability & Growth Strengths

Strong Market Position & Advantage: Independent analyst leadership and a large installed base signal a durable competitive position in P&C core platforms, reinforced by recognition from Gartner, Forrester, and Celent. A broad partner ecosystem and marketplace integrations further strengthen adoption and delivery at scale.

Strong Revenue Growth: Recent quarters and fiscal-year results indicate robust, double‑digit top‑line expansion, with subscription and support growing faster than overall revenue. Raised guidance and expanding remaining performance obligations support continued momentum.

Profitability: Earnings metrics improved meaningfully year over year, reflecting operating leverage as cloud revenue scales. Management highlighted stronger operating cash generation alongside growth in higher‑margin subscription revenue.

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.

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
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
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
Arbella Insurance Group
5 Offices
927 Employees
37 Benefits Hiring Now

Founded in 1988 in Quincy, Massachusetts, Arbella provides affordable car, home, and business insurance in Massachusetts and Connecticut, and business insurance in New Hampshire and Rhode Island. Our vision is to be the best property and casualty company in the Northeast. Period. We are proud to be consistently recognized as one of the Best Places to Work by the Boston...

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Arbella Insurance Group

Arbella Insurance Group's Top Stability & Growth Strengths

Profitability: Recent commentary notes significantly improved underwriting results and operating performance in 2024, attributed to pricing, underwriting, and claims initiatives. Feedback suggests these actions strengthened earnings quality and support disciplined growth.

Investor Backing & Capital Strength: Assessments describe very strong balance sheet strength, which underpins credibility with agents and policyholders in core markets. Feedback suggests this capital position provides resilience amid competitive and cyclical pressures.

Strong Market Position & Advantage: In its home market, the company maintains a durable position among larger Massachusetts auto writers and holds notable share in select commercial niches, supported by long-standing independent-agent distribution. Feedback suggests local brand recognition and agency relationships help sustain scale in competitive lines.

NEXT Insurance
Fintech • Insurance
5 Offices
651 Employees
31 Benefits Hiring Now
Next Insurance provides affordable and customizable policies to small business owners.

The needs of business owners have significantly changed over the past decade, the insurance industry hasn’t. When you’re running your own business, you’re placing a huge bet on yourself. Your ideas, your passion, your blood, sweat and tears define your success. Next Insurance was created to give your business the coverage it deserves. Simple, affordable and tailored. So no matter...

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NEXT Insurance

NEXT Insurance's Top Stability & Growth Strengths

Investor Backing & Capital Strength: Capital support is reinforced by a full acquisition by ERGO (Munich Re) and prior strategic investments tied to product and reinsurance partnerships, alongside financial‑strength upgrades in 2025–2026. These moves signal a stronger balance sheet, enhanced reinsurance access, and improved counterparty credibility.

Strategic Partnerships: Embedded distribution through platforms like Intuit QuickBooks and ties with Amazon Business Prime, plus alliances with major insurers, expand market reach and create durable access to SMB customers. Partner channels and agent initiatives are highlighted as ongoing levers for scale under the ERGO umbrella.

Strong Revenue Growth: Rising topline through 2024 and an increasing GWP run‑rate into late 2023 indicate meaningful momentum within the digital SMB segment. Customer counts moving materially higher through 2025 further support a trajectory of continued scale.

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.

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.

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
Fetch (fetchpet.com)
Insurance • Pet
6 Offices
44 Employees
32 Benefits

Hey there, we're Fetch — vets, data whizzes, techies, and insurance experts transforming the way we care for our pets. Working with dozens of Aussie pet parents and vets, we’ve rethought the system to be easier, fairer, and more connected. We’re building a subscription and accompanying app that brings together insurance, prevention, insights, and rewards to simplify pet health and help...

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Fetch (fetchpet.com)

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