HealthCare.com Secures $18 Million in Series B Funding to Expand Its Health Insurance Technology Solutions

The fastest-growing leader in technology-enabled health insurance solutions, today announced that it has secured $18 million in Series B funding, which brings the total capital raised to over $27 million. The financing will be used to grow HealthCare.com as the nation’s preeminent source helping consumers compare and enroll in health insurance and Medicare plans.

The round was led by Second Alpha Partners, a New York based private equity firm specializing in technology-enabled companies. Additional strategic participation included AXIS Capital and CNO Financial Group.

The InsurTech company will use the additional capital to fund technology, engineering and data-science investments, expand consumer experience solutions and accelerate the development and marketing of its proprietary insurance products.

“We recognize the massive opportunity and are committed to helping consumers deal with the increasing complexities and costs of health insurance,” added Jose Vargas, co-founder, and president of HealthCare.com. “We are pleased and honored to have the backing of investors who share our values and mission to become the pioneer tech-enabled destination for consumers to compare and enroll in health insurance and Medicare plans.”

“Second Alpha is pleased to back HealthCare.com and its entire team, who have demonstrated market leadership and momentum while building a sustainable and profitable InsurTech company,” said Jim Sanger, managing partner of Second Alpha Partners. “Applying technology and data to help consumers navigate and enroll in the best health insurance or Medicare plan is a massive and exciting opportunity.”


HealthCare.com was founded in 2014 and is led by a team of technology and insurance industry veterans including co-founders Howard YehJeff Smedsrud, and Jose Vargas. To date, the company has raised over $27 million from a diverse group of investors including Jeff Boyd, chairman of Booking Holdings, and PeopleFund.

About HealthCare.com
HealthCare.com is an online health insurance company providing a data-driven shopping platform that helps American consumers enroll in individual health insurance and Medicare plans. HealthCare.com also develops and markets a portfolio of proprietary, direct-to-consumer health insurance and supplemental insurance products under the name Pivot Health. Founded in 2014, the company is headquartered in New York City, and is backed by PeopleFund and individual investors including current and former executives of Booking.com and Priceline. HealthCare.com is a 4-time honoree of the Inc. 5000 list of America’s fastest-growing companies. For more info, visit www.HealthCare.com.

About Second Alpha Partners
Founded in 2012, Second Alpha Partners is a value-oriented private equity firm focused on secondary and secondary-linked direct investments in mature venture stage, growth equity and middle-market companies showing prospects for superior future growth. Second Alpha seeks to purchase full or partial equity and equity-linked positions from existing investors and founders (“secondary directs”), primarily focusing on North American technology, media, telecom, and tech-enabled services opportunities.

About AXIS Capital
AXIS Capital (NYSE: AXS), through its operating subsidiaries, is a global provider of specialty lines insurance and treaty reinsurance with shareholders’ equity at September 30, 2019, of $5.6 billion and locations in Bermudathe United StatesEuropeSingaporeCanada, and the Middle East. Its operating subsidiaries have been assigned a rating of “A+” (“Strong”) by Standard & Poor’s and “A+” (“Superior”) by A.M. Best. For more information about AXIS Capital, visit www.axiscapital.com.

About CNO Financial Group
CNO Financial Group, Inc. (NYSE: CNO) is a holding company. Our insurance companies – principally Bankers Life and Casualty Company, Colonial Penn Life Insurance Company and Washington National Insurance Company – primarily serve middle-income pre-retiree and retired Americans by helping them protect against financial adversity and provide for a more secure retirement. For more information, visit CNO online at www.CNOinc.com.

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