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Top Insurance Companies in Boston, MA (135)

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: Reporting indicates revenue increased in successive years, with UK results showing clear year-over-year gains and the parent highlighting category increases linked to the business. This pattern points to solid top-line momentum across core operations.

Profitability: Operating and post-tax profit improved materially, at times outpacing revenue growth. Such margin expansion suggests enhanced earning efficiency and disciplined execution.

Market Expansion: Customer reach advanced to a major UK milestone while U.S. distribution broadened through accelerated agent activity and additional channels. New insurer partnerships and digital launches further extend access to buyers.

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: Financial disclosures indicate total revenue increased from 2024 to 2025 alongside higher total reported sales, while operating earnings rose sharply. Together these patterns suggest momentum in top line and core operating performance.

Investor Backing & Capital Strength: Total adjusted capital increased from $33.2B to $34.4B, and an estimated $2.9B dividend was approved for eligible policyowners, supported by very strong insurer financial-strength ratings. These signals point to a robust balance sheet that underpins stability and growth capacity.

Diversified Revenue Streams: Expansion was described as broad-based across insurance, annuities, institutional solutions, and wealth management, with client assets in wealth management reaching a record $312B and total AUM at $584B. This mix reduces reliance on any single line of business and supports continued scale.

CarGurus
Consumer Web • eCommerce • Software
We're re-engineering car shopping. Join us for the ride.

Headquartered in Boston, Massachusetts, CarGurus is the #1 visited digital auto platform in the U.S. for shopping, buying, and selling new and used vehicles and an award-winning place to work. We give drivers and dealers the confidence to buy or sell cars exactly how they want: online, in-person, or a combination of both. Our culture fosters kindness, collaboration, and innovation,...

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CarGurus

CarGurus's Top Stability & Growth Strengths

Strong Revenue Growth: Revenue is rising at a low-double-digit pace, with FY 2025 up 14% and Q1–Q2 2026 growing 15% and 13% year over year. Evidence indicates this marked a second consecutive year of double-digit annual growth with continued momentum into 2026.

Profitability: Profitability expanded faster than sales in 2025, with adjusted EBITDA up 25% and GAAP net income from continuing operations up 53%. This pattern points to improved operating leverage, even as quarterly results vary.

Market Expansion: International and dealer-network metrics show expansion, with total paying dealers up about 5% and international dealers up 11% year over year; international revenue rose 28% in Q2 2026. These gains suggest growth beyond the U.S. base and higher monetization per dealer.

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

Investor Backing & Capital Strength: Recent financing rounds, including a $193 million raise in January 2025 and a subsequent growth investment in April 2026 with Allianz X participation, signal substantial capital support. Announcements indicate this funding is intended to power additional state entries, deeper agency relationships, and broader product offerings.

Market Expansion: Operating in 24 states with plans for further geographic reach, alongside a large and growing independent-agent network, points to widening distribution. Industry reporting also highlights increased written premiums and a larger set of agency relationships over recent years.

Strategic Partnerships: An expanded long-term reinsurance partnership with Allianz Re is presented as adding capacity to support scaling. Investor and partner updates emphasize collaboration aimed at advancing geographic expansion and product development.

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

Profitability: Reported net income rose materially in 2024 alongside stronger mortgage and securities‑based lending activity. Company reports indicate earnings momentum continued into 2025.

Market Expansion: Announced and opened full‑service branches in Boston’s Seaport, Falmouth, and Andover in 2026 indicate deliberate investment in new local markets. Additional hiring of private‑banking and nationwide SBA teams points to geographic and channel expansion.

Investor Backing & Capital Strength: Reported capital ratios are well above regulatory well‑capitalized thresholds, and a long‑running five‑star safety rating is cited. These indicators suggest capacity to fund growth while maintaining buffers.

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: Evidence indicates the 2026 acquisition of Urgently and added commercial roles broaden Agero’s reach across automotive, fleet, rental, and insurance, taking the combined platform to about 150 million vehicles and roughly 13–14 million annual service events. New and renewed programs further extend activity across roadside assistance, claims, and mobility services.

Strong Market Position & Advantage: Company materials describe service to approximately 150 million drivers, relationships with six of the top ten insurers, and a nationwide network of 8,000+ providers. External recognition such as Frost & Sullivan’s 2025 North American Company of the Year reinforces a durable competitive position in digitalized roadside assistance.

Strategic Partnerships: Renewals and wins like Hagerty and Virginia Farm Bureau Insurance, plus collaborations such as MOTER, point to deep, ongoing enterprise relationships. These ties support recurring service volumes and cross-sell opportunities across roadside, accident management, and connected-vehicle offerings.

Hi Marley
Artificial Intelligence • Cloud • Insurance • Software • Database • Conversational AI • Generative AI
Boston
140 Employees
52 Benefits Hiring Now
Hi Marley is the intelligent communication platform for P&C insurance.

Hi Marley is the Intelligent Communication Platform for P&C Insurance. Founded in 2017 and headquartered in Boston, Hi Marley helps carriers deliver better insurance experiences through communication that is simple, connected, and built for the way P&C teams work. Trusted by more than 130 carriers, including 4 of the top 10, Hi Marley connects carriers and the insurance ecosystem in...

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Hi Marley

Hi Marley's Top Stability & Growth Strengths

Strong Revenue Growth: Revenue is portrayed as having risen significantly over recent years, reflecting strong commercial momentum. Repeated acknowledgments of rapid multi-year growth support the view that top-line expansion has been substantial.

Strong Market Position & Advantage: Adoption reportedly spans more than 130 property-and-casualty carriers, including many top-tier insurers, indicating meaningful penetration in its niche. Named carrier relationships and integration within established insurance ecosystems reinforce credibility.

Product Line Growth: The company has expanded beyond claims communication into policyholder service, AI assistants, workflow automation, and a network connecting carriers with service providers. These moves suggest a broader addressable market and deeper value within existing accounts.

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: Profitability is improving markedly, with net income and underwriting results rising and a strong combined ratio in early 2026. Lower catastrophe losses and stronger investment income also supported these gains.

Investor Backing & Capital Strength: Capital strength is solidifying as equity increased and S&P upgraded core operating companies’ financial strength ratings to A+, citing improved underwriting and capitalization. This positions the company to pursue growth from a stronger balance sheet.

Future-Ready Strategy: Strategy is shifting from “fixing” to “building,” emphasizing selective, profitability-threshold growth in segments showing momentum like Global Risk Solutions. Management highlights disciplined expansion rather than growth at any cost.

Sittercity
Kids + Family • Software
Fully Remote
46 Employees
51 Benefits Hiring Now
Join us in reimagining something better.

Sittercity, a Bright Horizons company, is a technology platform working to reimagine the child care industry. Finding, hiring and managing high-quality, trustworthy and enriching child care has never been simple, for parents or caregivers. We want to change that. At Sittercity, you can imagine and create solutions that will revolutionize a multi-billion industry and bring relief to parents and care...

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Sittercity

Sittercity's Top Stability & Growth Strengths

Strong Revenue Growth: Parent company Bright Horizons’ back-up care segment, which includes Sittercity, reported notable revenue increases across recent years, indicating a favorable growth backdrop. Disclosures attribute gains to higher utilization of care services, placing Sittercity within a rising business line even if its standalone contribution is not broken out.

Investor Backing & Capital Strength: Ownership by Bright Horizons provides established capital support and integration into employer-sponsored care channels. Filings and corporate materials continue to identify Sittercity as an operated marketplace within this segment, underscoring ongoing commitment.

Innovation-Driven Growth: Recent platform improvements—such as enhanced messaging, application management, and AI-assisted posting—signal continued product investment. These updates suggest efforts to strengthen marketplace efficiency and user workflows.

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Babylist
eCommerce • Healthtech • Kids + Family • Retail • Social Media
4 Offices
300 Employees
44 Benefits Hiring Now
The trusted platform for millions of growing families, with products and services across commerce, media, and health.

Babylist is the trusted platform for millions of growing families. For over a decade, Babylist has been the technology solution for expecting parents and the community that supports them, expanding from baby registry into a full-service platform that helps parents make decisions with confidence, stay connected, and build happy and healthy families. Every year Babylist helps over 9M people make...

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Babylist

Babylist's Top Stability & Growth Strengths

Strong Revenue Growth: Revenue is described as rising rapidly, surpassing $750 million in 2025 with 45% year-over-year growth, alongside expanding customer reach. The multi-year trend from roughly $400 million in 2023 to $750 million-plus in 2025 points to sustained expansion across the core business.

Profitability: Profitability is reported for eight consecutive years through 2025, with adjusted EBITDA margin improving by five percentage points in 2025. This indicates expansion has been achieved without relying on sustained operating losses.

Diversified Revenue Streams: Growth extends beyond the registry into healthcare, media, retail, and financial services, with Health up 64% and Media up 35% year over year in 2025. Physical showrooms and fulfillment investments further support multiple avenues for monetization.

XDimensional Technologies, Inc.
Insurance • Software
Boston
67 Employees

For over two decades, XDimensional Technologies has been serving the insurance industry with innovative solutions that make business more efficient and productive throughout the insurance value chain. We work closely with our customers and partners to understand their evolving needs and issues, and then map those understandings into solutions that improve business results. And we assure our solutions are flexible...

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XDimensional Technologies, Inc.
NFP, an Aon company
15 Offices
4,449 Employees
37 Benefits

NFP, an Aon company, helps companies and individuals address today’s most significant Risk Capital and Human Capital challenges. With colleagues across the U.S., Canada, UK and Ireland, and global capabilities enhanced by the Aon advantage, NFP serves a diversity of clients, industries and communities. Our collaborative team provides specialized expertise and customized solutions, including property and casualty insurance, employee benefits,...

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NFP, an Aon company

NFP, an Aon company's Top Stability & Growth Strengths

Strong Market Position & Advantage: Evidence indicates NFP is a leading middle‑market broker and benefits consultant with durable scale, now operating as “NFP, an Aon company,” which amplifies its reach via Aon’s global platform. Industry rankings consistently place it in the upper tier of brokers, reinforcing competitive positioning in its core segment.

Market Expansion: Announcements show continued 2025–2026 activity including multiple tuck‑in acquisitions and a new National Flood Practice, extending capabilities and geographic footprint across the U.S., Canada, the U.K., and Ireland. This cadence reflects ongoing build‑out of niche specialties and regional presence.

Cost & Operational Efficiency: Aon’s commentary links NFP integration to restructuring savings and margin expansion, indicating operating leverage on a larger base. Filings confirm integration progress and portfolio focus actions that align cost structure with core broking and benefits.

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.

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
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.

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
One80 Intermediaries
Insurance • Financial Services
Boston
418 Employees
4 Benefits

One80 Intermediaries is a privately held firm with offices throughout the US and Canada. As a leading insurance wholesaler and program manager, the company offers placement services and binding authority for property and casualty, life, travel/accident and health, affinity and administrative services and warranty business. One80 serves commercial companies, non-profits, public entities, individuals and associations and unions, and has access...

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One80 Intermediaries
Blue Cross Blue Shield Association
8 Offices
3,161 Employees
23 Benefits

Blue Cross Blue Shield Association is a national federation of 34 independent, community-based and locally operated Blue Cross and Blue Shield companies that collectively provide health care coverage for one in three Americans. BCBSA provides health care insights through The Health of America Report series and the national BCBS Health Index.

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Blue Cross Blue Shield Association
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
Ledgebrook
Insurance • Financial Services
Needham
226 Employees
Modernizing the Specialty insurance industry

Ledgebrook is an InsurTech MGA on a mission to bring Specialty insurance into the modern era. Burdened with legacy technology and processes, the industry has not kept pace with the speed of innovation seen in other sectors. Positioned at the cutting edge of the next generation of InsurTech, Ledgebrook offers the best of both worlds: innovative world-class technology deployed by...

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Ledgebrook

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