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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.

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.

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.

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.

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.

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.

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.

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.

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Skyward Specialty Insurance
5 Offices
527 Employees
17 Benefits Hiring Now

Skyward Specialty is a rapidly growing and innovative specialty insurance company, delivering commercial P&C products and solutions on a non-admitted and admitted basis. The Company operates through eight underwriting divisions –Accident & Health, Captives, Global Property & Agriculture, Industry Solutions, Professional Lines, Programs, Surety and Transactional E&S. Our insurance company subsidiaries are rated A (Excellent) with stable outlook from AM...

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Skyward Specialty Insurance
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
Risk Strategies
Insurance
15 Offices
2,372 Employees
34 Benefits
Part of the Brown & Brown Team

At Risk Strategies, part of the Brown & Brown team, we help our clients protect those things that matter most to them. We help them see the way forward in a complex world with specialty insight, practical advice, and custom insurance with a vast network of specialists in Property & Casualty, Employee Benefits, Private Client, as well as Consulting Services...

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Risk Strategies

Risk Strategies's Top Stability & Growth Strengths

Strong Market Position & Advantage: Industry league tables place the Accession platform (Risk Strategies and One80) in the top tier of U.S. brokers by brokerage revenue, supporting the view that the business holds meaningful scale and competitiveness in its core markets.

Strong Revenue Growth: Reported figures describe a sustained upward revenue trajectory across multiple years, including pro forma growth through 2024 and earlier step-ups attributed to a mix of organic expansion and acquisitions.

Investor Backing & Capital Strength: Ownership under Brown & Brown following the acquisition of Accession is positioned as providing a larger platform, added resources, and broader market access that can support continued expansion and resilience.

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
Manulife
Fintech • Insurance • Financial Services
26 Offices
32,427 Employees
7 Benefits Hiring Now

Manulife is a leading international financial services group that helps people make their decisions easier and lives better. With our global headquarters in Toronto, we operate as Manulife across our offices in Canada, Asia, and Europe, and primarily as John Hancock in the United States. We have more than 40,000 employees, over 116,000 agents serving ~34 million customers worldwide, and...

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Manulife

Manulife's Top Stability & Growth Strengths

Strong Revenue Growth: Analysts forecast a sharp jump in revenue over the next year and continued earnings expansion through 2026–2028, indicating strong near-term growth expectations.

Investor Backing & Capital Strength: Capital and solvency indicators are positioned as robust, including an A+ financial strength rating and a strong LICAT ratio, alongside sizable remittances and ongoing shareholder returns.

Strong Market Position & Advantage: The company is described as a category leader in Canada with top-tier positions in multiple Asian markets, supported by large AUMA/AUMA scale and a long operating history that reinforces competitive standing.

Brighthouse Financial
5 Offices
1,300 Employees
20 Benefits

We're Brighthouse Financial. We are on a mission to help people achieve financial security. As one of the largest providers of annuities and life insurance in the U.S., we specialize in products designed to help people protect what they’ve earned and ensure it lasts. We are built on a foundation of experience and knowledge, which allows us to keep our...

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Brighthouse Financial
LTCG
Insurance
11 Offices
1,001 Employees
25 Benefits

LTCG is a leading provider of business process outsourcing for the insurance industry. The nation's largest insurers rely on our unparalleled expertise to help manage their complex long-term care portfolios and maximize financial performance. We also provide clients with advanced risk management insight built upon our unique and proprietary long-term care underwriting and claims databases. LTCG has more than 1.4 million...

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LTCG
National Financial Partners
Insurance • Consulting
14 Offices
3,409 Employees
37 Benefits

NFP is a leading property and casualty broker, benefits consultant, wealth manager, and retirement plan advisor. We enable client success through specialized expertise, innovative technologies, and enduring relationships with highly rated insurers, vendors and financial institutions. With a growing number of employees located around the world, we are experts, leaders and advocates, all coming together to work towards one goal...

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National Financial Partners
FINEOS
Insurance • Software
10 Offices
756 Employees
10 Benefits

FINEOS is a leading provider of core systems for life, accident and health insurers globally with 7 of the 10 largest group life and health carriers in the US as well as 6 of the largest life insurers in Australia. With employees and offices throughout the world, FINEOS continues to scale rapidly, working with innovative progressive insurers in North America,...

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FINEOS
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
Chronovo
Insurance
Burlington

Chronovo is a new force in the structured settlement annuity marketplace. A service-driven, tech-enabled revolution in effortless, comprehensive quoting and negotiations, we make everything simple, transparent and empowering for claimants, counsel and claims professionals.

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Chronovo

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