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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.

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.

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.

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.

Marsh
Insurance
36 Offices
27,671 Employees
37 Benefits

Possibility. We seek better ways to manage risk and define more effective paths to the right outcome. We go beyond risk to rewards for our clients, our company, our colleagues, and the communities in which we serve. Marsh, a business of Marsh McLennan (NYSE: MMC), is the world’s top insurance broker and risk advisor. Marsh McLennan is a global leader in...

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Marsh

Marsh's Top Stability & Growth Strengths

Strong Revenue Growth: Reported and underlying revenue increased across 2024 and into 2025, with steady mid‑single‑digit organic gains supplemented by acquisitions and double‑digit reported growth in several quarters. Feedback suggests the brokerage unit saw broad‑based geographic contributions alongside margin expansion at the consolidated level.

Strong Market Position & Advantage: Industry rankings consistently place the firm as the world’s largest insurance broker by revenue, including holding the top U.S. position, reinforcing scale advantages and market access. Feedback suggests this leadership has been maintained despite consolidation and shifting share at the margins.

Future-Ready Strategy: Management is unifying the brand as “Marsh” and centralizing data/AI and operations through a new Business & Client Services unit to accelerate growth and efficiency. Feedback suggests ongoing investments in a firm‑wide brand and operating model are designed to enable longer‑term, tech‑enabled growth.

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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)
Health Care Service Corporation
Healthtech • Insurance
30 Offices
13,563 Employees
46 Benefits

Imagine Something New, Something Different. Health Care Service Corporation, a Mutual Legal Reserve Company (HCSC), is the largest customer-owned health insurer in the nation and the fourth largest overall. Operating through our Blue Cross and Blue Shield Plans in Illinois, Montana, New Mexico, Oklahoma and Texas (as well as a variety of affiliates and subsidiaries,) we are expanding access to high-quality,...

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Health Care Service Corporation

Health Care Service Corporation's Top Stability & Growth Strengths

Strong Revenue Growth: Revenue grew meaningfully in 2023 and 2024, with a further sizable increase projected for 2025 following the Medicare acquisition. The top line is supported by expanding membership across commercial, individual, and Medicare segments.

Strong Market Position & Advantage: The company holds leading positions in its five core states and benefits from the well-known Blue Cross Blue Shield brand. It ranks among the largest U.S. health insurers and maintains strong financial strength ratings.

Market Expansion: The acquisition of Cigna’s Medicare business and multi‑year Medicare Advantage county additions have extended reach from five core states to a national Medicare footprint. Physical footprint investments and broader product availability further signal ongoing expansion.

EverQuote
Artificial Intelligence • Consumer Web • Fintech • Insurance
5 Offices
375 Employees
At EverQuote we deliver better results for our P&C clients' digital marketing programs.

EverQuote empowers the largest insurance carriers and thousands of agents to maximize customer acquisition across digital channels. Fueled by our proprietary data assets and AI traffic engine, EverQuote is transforming how providers attract and engage customers to grow market share.

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EverQuote

EverQuote's Top Stability & Growth Strengths

Strong Revenue Growth: Revenue is rising again, with multiple quarters described as record and guidance indicating continued year-over-year gains. Momentum is supported by a rebound in auto and expansion in home and renters.

Profitability: Earnings are improving, highlighted by positive net income and record Adjusted EBITDA alongside stronger margins. Management characterizes recent results as delivering higher profitability versus prior periods.

Healthy Cash Flow: Cash generation and liquidity appear solid, with record operating cash flow, a sizable cash balance, and no debt reported. This provides flexibility to navigate industry cycles and fund growth.

Principal Financial Group
Fintech • Insurance
26 Offices
18,000 Employees
36 Benefits Hiring Now

Principal Financial Group provides retirement savings, investment, and insurance products and services worldwide.

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Principal Financial Group

Principal Financial Group's Top Stability & Growth Strengths

Profitability: Non‑GAAP operating EPS rose 11% in 2024 and accelerated at double‑digit rates in 2Q–3Q25, with segment margin expansion supporting earnings momentum.

Investor Backing & Capital Strength: Management raised dividends multiple times in 2025 and executed ongoing buybacks consistent with annual capital deployment guidance, indicating balance‑sheet flexibility and disciplined return of capital.

Strong Market Position & Advantage: The company is a leader in SMB/pooled retirement solutions, plan‑sponsor experience, and real‑estate investing while remaining a credible scaled competitor across broader retirement and asset‑management markets.

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.

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
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
Allina Health
Healthtech • Insurance • Professional Services • Telehealth
24 Offices
29,000 Employees
23 Benefits

Allina Health is a nonprofit health care system based in Minneapolis, Minnesota, that owns or operates hospitals and clinics throughout Minnesota and western Wisconsin, focused on improving patient outcomes and community health.

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Allina Health
Hays Companies
Insurance • Consulting
3 Offices
940 Employees
3 Benefits

Hays Companies is a risk management, insurance, and employee benefits consultancy firm, driven to deliver the highest quality, customer-focused service.

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Hays Companies
Insurify
Artificial Intelligence • Consumer Web • Fintech • Insurance
Cambridge
250 Employees
17 Benefits Hiring Now

Insurify is one of America’s fastest-growing MIT FinTech startups and has been recognized as one of Inc. 5,000’s fastest-growing private companies in America in 2025, 2024, 2023, 2022 and 2021, Forbes Fintech 50 List for 2023, 2022, and 2021, Forbes Next Billion Dollar Startups of 2022 global and Top 100 InsurTech company. We’re changing the way millions of people compare,...

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Insurify

Insurify's Top Stability & Growth Strengths

Strong Revenue Growth: Annual recurring revenue is described as rising year over year, alongside increasing quote volume and monthly active users. Net losses are also described as narrowing, which aligns with improving operating leverage even if profitability has not been reached.

Investor Backing & Capital Strength: The company is described as venture-funded with multiple funding milestones and extensions, indicating access to capital to support continued scaling. Valuation references and named investors are presented as signals of sustained investor confidence.

Market Expansion: Operations are described as expanding geographically and into additional insurance lines beyond auto, alongside new product launches and embedded/white-label efforts. These moves indicate a broader go-to-market footprint and more routes to growth.

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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