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Top Insurance Companies in Pittsburgh, PA (26)

Penn National Insurance
4 Offices
805 Employees
3 Benefits Hiring Now

We sell a diverse array of business insurance, and auto and homeowners insurance. We sell only through independent insurance agents. Independent insurance agents can sell for a variety of insurance companies. Their customers can feel secure, knowing that their agent is looking out for their best interest and matching them with the best insurance carrier to meet their unique needs. We...

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Penn National Insurance
Reliance Matrix
Insurance • Financial Services
19 Offices
1,286 Employees
21 Benefits Hiring Now

Reliance Matrix delivers employee benefits, absence management and workforce productivity solutions through the financial stability of a top-rated insurance carrier, the agility and innovative spirit of a Third Party Administrator (TPA), and the daily commitment of thousands of team members across America. Where larger competitors offer size, we inspire confidence and long term engagement through integration, reliability and dedication to...

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Reliance Matrix

Reliance Matrix's Top Stability & Growth Strengths

Strong Market Position & Advantage: Evidence indicates the company leads in outsourced absence/leave administration with meaningful scale across employees covered. An integrated single‑intake platform and 24/7 contact centers reinforce differentiation for employers consolidating vendors.

Investor Backing & Capital Strength: Parent backing within a large global insurance group and strong claims‑paying capability support long‑term stability. This lowers counterparty risk for multi‑year benefit commitments.

Product Line Growth: Recent enhancements, including expanded critical illness coverage and a small‑business solutions suite, signal ongoing broadening of offerings. Continued technology and IP investment complements the product roadmap.

Arias Agencies
Insurance • Financial Services
6 Offices
395 Employees
Hiring Now

Arias Agencies is a life insurance organization founded by Simon Arias. It works with unions and families to provide life, supplemental health, and employee benefit plans, including enrollment and ongoing benefit support. The company has expanded across multiple U.S. offices and emphasizes protecting families, serving local communities, and offering purposeful career opportunities in the insurance and benefits field as it...

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Arias Agencies
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.

Western & Southern Financial Group
Fintech • Insurance • Financial Services
26 Offices
4,600 Employees
24 Benefits Hiring Now

We can help you reach your goals and achieve your dreams by assisting you with insurance protection, investments and retirement planning. We're here for you. Founded in Cincinnati in 1888 as The Western and Southern Life Insurance Company, Western & Southern Financial Group, Inc. has grown into a diversified family of financial services companies that includes the following: *The Western and...

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Western & Southern Financial Group
HUB International
44 Offices
10,055 Employees
35 Benefits Hiring Now

Hi, we’re HUB. We advise businesses and individuals on how to reach their goals. When you partner with us, you’re at the center of a vast network of risk, insurance, employee benefits, retirement and wealth management specialists that bring clarity to a changing world with tailored solutions and unrelenting advocacy. So you’re ready for tomorrow. About Hub International Headquartered in Chicago, Illinois, Hub...

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HUB International

HUB International's Top Stability & Growth Strengths

Strong Market Position & Advantage: HUB International is positioned as a top-tier global broker by revenue and is frequently characterized as a leader in the North American middle market, supported by broad capabilities across commercial, benefits, retirement, and wealth.

Investor Backing & Capital Strength: The company secured a large minority equity raise at a record private-broker valuation, with proceeds explicitly tied to funding continued acquisitions, investment, and balance-sheet actions such as deleveraging.

Strong Revenue Growth: Revenue is described as having increased materially over the past decade with continued year-over-year growth and forward projections indicating additional scaling in the near term.

Cigna
Healthtech • Insurance
25 Offices
74,000 Employees
43 Benefits Hiring Now

At Cigna, we're more than a health insurance company. We are your partner in total health and wellness. And we’re here for you 24/7 – caring for your body and mind. As a global health service company, Cigna's mission is to improve the health, well-being, and peace of mind of those we serve by making health care simple, affordable, and predictable. Our...

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Cigna

Cigna's Top Stability & Growth Strengths

Profitability: Cigna is described as reporting strong profitability through 2025, with multi‑billion profits and guidance pointing to higher EPS. Evernorth is positioned as the primary earnings engine supporting that profitability.

Strong Revenue Growth: Total revenues are described as rising strongly through 2024 and 2025, with continued growth implied by 2026 adjusted revenue guidance. Growth is characterized as being driven primarily by Evernorth’s PBM, specialty pharmacy, and care services businesses.

Future-Ready Strategy: The company is portrayed as intentionally shifting to a services‑led model after the Medicare divestiture, emphasizing specialty pharmacy, behavioral health, and a move toward a rebate‑free PBM approach. This repositioning is framed as an adaptation to evolving market expectations around transparency and affordability.

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.

Howard Hanna Real Estate Services
Insurance • Real Estate • Financial Services
9 Offices
8,678 Employees
Hiring Now

Howard Hanna Real Estate Services is a leading family-owned, full-service real estate company and one of the largest in the United States. They provide comprehensive real estate, title, insurance, and mortgage services to clients across 13 states, operating over 480 offices with a team of approximately 15,000 sales associates and staff.

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Howard Hanna Real Estate Services
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Foresters Financial
Insurance • Financial Services
25 Offices
1,509 Employees
9 Benefits Hiring Now

Foresters Financial is redefining the life insurance and individual savings industry across the U.S., Canada and UK by enriching the lives, communities, and overall well-being of its members. Agents and members alike appreciate the turnkey-decisioned product offerings and end-to-end digitized processes that make it easy to get life insurance without traditional medical exams. State-of-the-art mobile tools help agents deliver tailored...

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Foresters Financial
Gateway Financial Group
Pittsburgh
24 Employees

Gateway Financial is a national independent insurance advisory firm founded in 1982. We specialize in consultative analysis and the strategic application of insurance products to solve the unique needs of ultra-high net worth private clients, business owners, national and international law firms, large and mid-size businesses, professional sports franchises, and Fortune 500 companies. Our team is committed to providing the...

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Gateway Financial Group
Highmark Wholecare
Healthtech • Insurance • Telehealth
Pittsburgh
1,000 Employees
17 Benefits

Highmark Wholecare is dedicated to caring for the whole person by coordinating health care through its Medicaid and Medicare programs, aiming to help members achieve optimal physical and whole-person health.

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Highmark Wholecare
HM Insurance Group
Pittsburgh
334 Employees

HM Insurance Group works to protect employers and health care entities across the country from the financial risks associated with catastrophic health care costs. With nearly 40 years in the market, HM Insurance Group is among the top carriers nationally for Stop Loss insurance, protecting self-funded clients from the financial loss associated with unexpected large or catastrophic claims. Similarly, HM...

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HM Insurance Group
Henderson Brothers Inc.
Pittsburgh
184 Employees
1 Benefits

Since 1893, generations have turned to Henderson Brothers for insurance and expertise to shield them from risk in both good times and bad. Today, we offer insurance and consultation to customers both regionally and internationally. Our deep bench of more than 175 experts is ready to assist you plus provide access to many of the nation’s largest and most respected...

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Henderson Brothers Inc.
Lifetime Quality Roofing and Storm Restoration, LLC
Insurance • Professional Services • Real Estate • Solar
14 Offices
225 Employees

Lifetime Quality Roofing and Storm Restoration, LLC is an award-winning provider of residential and commercial roofing, siding, gutter, and exterior services with lifetime warranties. Operating since 2015, the company serves homeowners and businesses across multiple states, including Ohio, Pennsylvania, Florida, North Carolina, Tennessee, and Texas, specializing in expert roof installations, repairs, and insurance-covered storm restoration.

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Lifetime Quality Roofing and Storm Restoration, LLC
Highmark Blue Shield
6 Offices
5,600 Employees
30 Benefits

Highmark Inc. is a health and wellness organization located in Pittsburgh and operates health insurance plans in Pennsylvania, Delaware, and West Virginia.

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Highmark Blue Shield
Koop Technologies
Artificial Intelligence • Automotive • Big Data • Insurance • Machine Learning
Pittsburgh

We're hiring! Please contact us if you're interested in exploring exciting positions across software engineering, product development, insurance, and sales at Koop. Koop is an insurance technology company specializing in autonomous vehicle, robotics, and machine-centric risks. We built a modular, API-powered insurance platform that enables data collection, underwriting, and claims handling of AV risks in a cost-efficient, scalable manner. As autonomy...

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Koop Technologies
BOST
Insurance
Pittsburgh
178 Employees

For over 30 years, our benefits expertise and advanced capabilities have enabled BOST to become one of the most trusted employee benefit solutions and administration companies in America. The BOST brand was founded to empower individuals, families, brokers, small businesses, non-profits and Fortune 500 companies with Benefits that Matter MOST. When you choose BOST, you choose a national, industry-leading organization that...

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BOST
Alera Group
Insurance
34 Offices
2,034 Employees
29 Benefits

Alera Group, formed in early 2017, has over 3,500 employees serving thousands of clients nationally. We have specialists in employee benefits, property and casualty, wealth and retirement plan services. Alera Group was created by the merging of 24 high-performing, entrepreneurial offices across the United States. Now, with new partner acquisitions across the country, we are serving clients with national expertise...

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Alera Group
AAA East Central
Pittsburgh
394 Employees

Legendary Locations For more than a century, AAA has provided legendary service to a geographically vast market that encompasses sections of Pennsylvania, Ohio, Kentucky, West Virginia, and New York. Today, AAA East Central serves more than 2.7 million members and has branches serving Pittsburgh, Cleveland, Allentown and Louisville, among other cities. AAA has opportunities for you to make a positive difference...

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AAA East Central

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