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Top Insurance Companies in Boston, MA (108)

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: Revenue is reported to have risen from £169.4m in 2023 to £197.0m in 2024, based on filed UK statutory accounts. Parent-company commentary for 2025 further points to higher “Other revenues” tied to this unit, reinforcing the upward trend.

Profitability: Operating profit increased to £45.9m in 2024 alongside higher profit after tax, indicating improved operating leverage. These gains are documented in UK filings as summarized by industry coverage.

Market Expansion: Customer milestones include surpassing one million globally in 2024 and one million in the UK in 2026, while a new Boston headquarters signals continued U.S. investment. Recent product and initiative rollouts (e.g., AI tools and community programs) indicate ongoing expansion efforts.

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

Profitability: Operating earnings are reported at nearly $3.9 billion for 2025, an all-time high. A record estimated 2026 policyowner dividend further signals strong underlying earnings capacity.

Strong Revenue Growth: Total sales surpassed $43 billion in 2025, up from 2024 levels. Company disclosures also indicate higher total revenue year over year.

Investor Backing & Capital Strength: Total adjusted capital increased to $34.4 billion in 2025, alongside affirmations of very high financial strength ratings from major agencies. These indicators are presented as continued balance-sheet resilience.

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: Recent capital raises include a $56.1M Series C in July 2024 and additional growth financing in March 2026 to expand product, sales, and customer success. These transactions point to strong investor support and resources to scale.

Product Line Growth: New and enhanced offerings such as the Group Health Risk Management Life Cycle (Sept 2025) and workers’ comp tools like ClaimVector and a 2026 triage solution indicate active product development. This expansion supports broader use cases across underwriting and claims.

Strong Revenue Growth: Company communications highlight double‑digit year‑over‑year growth since founding and well over 100% growth exiting 2022, with a later 50% YoY increase in platform volume. These signals suggest ongoing commercial momentum.

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: Deloitte’s 2025 Technology Fast 500 ranked the company No. 244 with 325% growth, following a 2023 placement at No. 67 with 2,263% growth. These recognitions indicate sustained multi‑year top-line expansion.

Strategic Partnerships: Carrier and ecosystem ties continue to expand, including Heritage Insurance enabling text-to-start claims in 2025 and company-highlighted expanded partnerships and integrations. Such relationships point to continued carrier adoption and embedded workflows.

Product Line Growth: The August 4, 2026 launch of Unite and the June 10, 2026 agentic‑AI strategy—alongside expansion into policyholder service—show active investment and new capabilities. These moves broaden the platform beyond claims into multi‑party coordination and service operations.

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: Total assets have climbed from about $4.6B at year‑end 2024 to roughly $5.28B by Q2 2026, extending a multi‑year rise noted in the bank’s own reports. Regulatory snapshots in 2025–2026 align around $5.0B+ in assets, indicating continued balance‑sheet expansion.

Market Expansion: Branch additions in 2026 (Boston Seaport/Back Bay, Andover, Falmouth) and the launch of new teams, including a nationwide SBA group and a West Coast deposit team, point to active geographic and channel growth. Leadership has framed these moves as organic expansion amid broader industry consolidation, with the Falmouth opening publicized.

Strong Market Position & Advantage: In Massachusetts home‑purchase mortgages, the institution is cited as the top bank lender for 2025 by both dollar volume and loan count. A June 2026 HMDA‑based composite also ranked it first overall in the state, signaling durable competitive strength in this niche.

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: Earnings and underwriting margins improved materially, with a full‑year 2025 combined ratio of 88.4% and year‑to‑date 87.3% in the first half of 2026 alongside higher net income. First‑half 2026 net income reached $4.686B versus $2.870B a year earlier, reflecting stronger underwriting and lower catastrophe losses.

Investor Backing & Capital Strength: Total equity increased to $44.1B by June 30, 2026, and core operating companies were upgraded to A+ by S&P on July 21, 2026. These markers indicate a fortified balance sheet and capacity to support selective expansion.

Resilient & Sustainable Growth: Deliberate portfolio pruning and disciplined underwriting (e.g., sale of Western European operations and other exits) reduced reported premiums while aiming to raise returns and lower volatility. The approach is characterized as “growing better” rather than “growing bigger,” prioritizing margin quality over 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

Market Expansion: Geographic availability has reached 24 states with recent entries in Connecticut, Virginia, and Delaware, and additional states flagged as coming soon. This footprint and pipeline indicate ongoing expansion through the independent‑agent channel.

Investor Backing & Capital Strength: A new growth investment closed in April 2026, alongside prior financing, is explicitly aimed at funding more states, deepening agency relationships, and broadening products. This signals ample capital support to scale in a complex homeowners market.

Strategic Partnerships: An expanded long‑term reinsurance partnership with Allianz Re provides added capacity to support growth and manage volatility. Admitted carrier partners such as Rock Ridge (A‑ AM Best) underpin distribution credibility and scaling capacity.

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: A completed acquisition of Urgently and higher stated coverage—about 150 million drivers and roughly 14 million annual events versus lower figures in 2019–2020—indicate a larger footprint. Industry recognition and growth forecasts for roadside assistance provide supportive category tailwinds.

Strategic Partnerships: Multi-year renewals with Hagerty and long-standing OEM relationships such as Ford, plus wins in fleet/telematics channels (e.g., Geotab), signal retention and new routes to market. Additional insurer partnerships like Virginia Farm Bureau broaden channel access.

Product Line Growth: Crash Response deployments expanded after significant 2023 gains, with calls up sharply since launch and dispatch volumes doubling as more top carriers adopted the service. Emphasis on the Swoop platform and automation supports continued product-led scaling.

Bindable
Insurance
Boston
56 Employees

Headquartered in Boston, Massachusetts, Bindable is the InsurTech leader for alternative distribution solutions, enabling organizations across all industries to drive revenue and build brand loyalty through digital insurance offerings. The proprietary Bindable platform brings together a digital insurance marketplace, PolicyCrusher® agent software, and a full suite of support services to offer flexible, market-ready solutions for insurers, agencies, brokerages, and trusted...

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Bindable
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Wunderite
Big Data • Insurance • Analytics
Boston
24 Employees

We are insurance agents and business owners at our roots. Some of us have been in insurance for over a decade. We are all on a mission to build the best software for independent insurance agencies. Co-founders Peter and Joe met on the first day of their MBA program at Boston College. Peter came from a family insurance agency, where he sold...

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Wunderite
Brown & Brown
Insurance
27 Offices
2,612 Employees
36 Benefits

At Brown & Brown, our guiding principles include building our team with the highest quality people and delivering innovative solutions and superior service. If you are a highly complex multinational company, an individual or anything in between, our experienced teams can help you view, analyze and purchase insurance efficiently. You will receive the personalized, dedicated service you deserve while leveraging...

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Brown & Brown
Sun Life Financial Inc.
Insurance • Financial Services

Sun Life is a leading international financial services organization providing protection and wealth products, financial planning, and retirement solutions, helping clients achieve lifetime financial security and live healthier lives.

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Sun Life Financial Inc.
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
Family Heritage Life Insurance Company of America
77 Offices
961 Employees
10 Benefits

Globe Life - Family Heritage Division is a wholly owned subsidiary of Globe Life Inc. (NYSE: GL). People of all backgrounds call Globe Life - Family Heritage Division home. We provide you with training to be successful leaders in an insurance sales career with us. Individuals willing to work hard and learn, can achieve their dreams and goals, all while...

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Family Heritage Life Insurance Company of America
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
Metromile
Insurance
3 Offices
280 Employees
20 Benefits

On the off chance you've thought about insurance, it's likely because you've insured something you love, not because you loved your insurance company. Metromile is out to change that. As an insurtech powered by data science and customer-centric design, we’re reimagining insurance to make it fairer and actually delightful. We’re obsessed with savings, service, and features that engage a customer...

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Metromile
AssuriCare
Insurance • Software
Waltham
63 Employees

Since 2010, AssuriCare has revolutionized the way people find, manage and pay for long-term care, the way providers manage and grow their businesses, and the way payers and administrators receive, evaluate and process long-term care claims. To date, tens of thousands providers and caregivers have used the AssuriCare platform to find and manage care, make payments and submit insurance claims,...

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AssuriCare
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.

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
Greater New York Insurance Companies
Insurance • Real Estate
5 Offices
292 Employees
31 Benefits

Greater New York Insurance Companies are leading providers of middle market property and casualty insurance focusing on commercial real estate, including condominiums, co-op apartment buildings, office buildings, restaurants, light manufacturing, and other small to mid-size commercial establishments. The lead company was formed as a mutual insurance company in 1914 as an outgrowth of a real estate trade association servicing New...

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Greater New York Insurance Companies

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