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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.

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.

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.

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.

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
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AIG
Insurance
32 Offices
49,681 Employees
47 Benefits Hiring Now

We're a leading global insurance organization with operations in more than 80 countries and jurisdictions. We provide a wide range of property casualty insurance, life insurance, retirement solutions, and other financial services to support our clients in business and in life through our General Insurance, Life & Retirement and Investments business units. What unites us across all of these offerings is...

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AIG

AIG's Top Stability & Growth Strengths

Profitability: Underwriting performance is described as improving, with combined ratios consistently below 100 and underwriting income rising, indicating stronger core earnings quality. Adjusted after-tax income per share is also described as increasing meaningfully, reinforcing profitability momentum.

Investor Backing & Capital Strength: Financial strength momentum is indicated by multiple rating upgrades from major agencies, supporting confidence in balance-sheet strength for large, complex programs. Significant capital returns through buybacks and dividends are highlighted as further evidence of capital flexibility and confidence.

Strong Market Position & Advantage: AIG is positioned as a top-tier player in U.S. commercial lines and a leader in complex commercial, multinational programs and specialty/E&S segments. The business is portrayed as particularly strong where scale, underwriting expertise, and high-limit capabilities matter most.

Telamon Insurance & Financial Network LLC
Agency • Insurance • Professional Services • Financial Services
Westwood
17 Employees

Telamon Insurance & Financial Network is an independent insurance agency founded in 1977. It specializes in providing a variety of specialty and traditional wholesale insurance services, acting as a single-source partner for insurance, employee benefit, and HR solutions. Leveraging a network of over 70 carrier relationships, Telamon provides expert guidance and exclusive programs to independent agents and their clients across...

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Telamon Insurance & Financial Network LLC
LP Insurance Services
12 Offices
114 Employees

Welcome to the LP Insurance Services company page of Linked In. We're glad you're visiting! Here you will learn about our company, products, services, programs, people and industry. We hope you find it informative and insightful. Please visit often as we aim to be useful to you! We'd also love for you to join us at www.lpins.net. We're an established...

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LP Insurance Services
ExamWorks
Insurance
21 Offices
555 Employees
22 Benefits

ExamWorks|Independent Medical Examinations, Peer Reviews, Bill Reviews

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ExamWorks
Strategic Risk Solutions
5 Offices
193 Employees
20 Benefits

Strategic Risk Solutions is a leading independent insurance management firm with representation in all major onshore and offshore domiciles. It provides financial reporting, regulatory compliance and underwriting management services to existing and prospective captive insurance companies. SRS was ranked the 4th largest captive manager worldwide and the largest independent by Business Insurance at December 31, 2020. For many people, captive management...

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Strategic Risk Solutions
Spotted Media
Big Data • Insurance • Analytics
Boston
16 Employees

SpottedRisk is a specialty MGA that launched in 2019, following its genesis as a data & analytics company in 2016. The company develops and distributes insurance products for complex risks in market segments that are underserved or suffering dislocation, creating products such as Disgrace Insurance, COVID cover for film and television production, Event Cancellation, and other unique products in the...

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Spotted Media
Enservio
Insurance
Needham
150 Employees

About Enservio: Enservio® blends digital technology with human expertise to provide risk–free solutions for the entire contents claims process. Insurance carriers rely on the Enservio platform and services to achieve the optimal business outcome for their contents programs, driving superior policyholder satisfaction and efficient workflow. Founded in 2004, we are headquartered in Needham, MA, with offices and professional staff across the...

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Enservio
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.

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
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
Newfront
Insurance
12 Offices
675 Employees
26 Benefits
De-Risking Human Progress

With elite insurance expertise empowered by breakthrough technology, Newfront is the modern insurance brokerage for the 21st century. With hundreds of veteran brokers and dedicated service professionals, we combine domain expertise with data-driven market intelligence to support our clients.

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Newfront

Newfront's Top Stability & Growth Strengths

Strong Revenue Growth: Organic revenue expanded steadily over multiple years, and industry rankings placed the firm among the Top 40 U.S. brokers by revenue. Evidence suggests continued momentum with reported gains in 2024 U.S. brokerage revenue and improved national standing.

Investor Backing & Capital Strength: The company secured substantial funding and achieved a multibillion-dollar valuation, signaling strong external capital support. Its sale to WTW for a transaction value up to the low billions further underscores recognized value and access to resources.

Innovation-Driven Growth: The firm differentiates through proprietary, AI-enabled technology that streamlines broking and benefits workflows. Awards and the acquirer’s stated rationale point to technology as a core driver of expansion and competitive advantage.

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