# HealthCare.com
HealthCare.com is an American insurtech company, founded in 2014 and headquartered in New York City and Miami, Florida, that develops and markets proprietary direct-to-consumer insurance and pharmacy plan products and uses machine learning to match consumers with health plans; it reached a valuation of more than $1 billion after a $180 million financing round in December 2021 and a $31.5 million extension of that round in February 2022.[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) • [2](https://www.hildred.com/news/healthcare-com-extends-previously-announced-financing) • [3](https://www.fiercehealthcare.com/tech/insurtech-platform-healthcare-com-banks-180m-boosts-valuation-to-1b)
| Fact | Detail |
| --- | --- |
| Founded | 2014[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) |
| Headquarters | New York City and Miami, Florida[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) |
| Co-founders | Jeff Smedsrud, Jose Vargas, and Howard Yeh[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) |
| Sector | Online healthcare / insurtech (direct-to-consumer insurance and pharmacy plans)[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) • [6](https://www.lifeinsuranceinternational.com/news/insurtech-platform-healthcare-com-series-c-extension/) |
| Series C | $180 million, December 13, 2021, led by Oaktree; extended to $211.5 million on February 8, 2022 with $31.5 million from Hildred Capital[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) • [2](https://www.hildred.com/news/healthcare-com-extends-previously-announced-financing) |
| Valuation | More than $1 billion at the December 2021 round[3](https://www.fiercehealthcare.com/tech/insurtech-platform-healthcare-com-banks-180m-boosts-valuation-to-1b) • [4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/) |
| Last sourced event | February 8, 2022 (Series C extension); no sourced record after that date[2](https://www.hildred.com/news/healthcare-com-extends-previously-announced-financing) |
## History and founders
The company was founded in 2014. As of the December 2021 financing announcement, all three original co-founders, Jeff Smedsrud, Jose Vargas, and Howard Yeh, remained active in senior leadership roles within the company.[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) At the same round, Brian Laibow of Oaktree Capital Management and Linda Ventresca of AXIS Capital joined the board.[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) By that time Don Loonam was serving as chief executive, per Refresh Miami's reporting on the round.[4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/)
## Products and services
HealthCare.com enables users to explore, select, and buy health insurance and other healthcare-related products, in trade press's description.[6](https://www.lifeinsuranceinternational.com/news/insurtech-platform-healthcare-com-series-c-extension/) The company develops and markets proprietary direct-to-consumer insurance and pharmacy plan products rather than operating only as a comparison site.[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) According to CEO Don Loonam, it uses machine learning and AI to match consumers with health plans, pharmacy plans, and its own insurance plans.[4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/) In connection with the February 2022 extension, co-founder Jose Vargas said the company had acquired a direct-to-consumer pharmacy with the capability of dispensing in all 50 states, which he said would be "a really large piece of our business" going forward.[5](https://refreshmiami.com/news/healthcare-com-raises-additional-31-5-million-extending-its-180-million-round/)
## Funding, by the numbers
Before 2021 the company had raised roughly $34.5 million, per Refresh Miami.[4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/) On December 13, 2021, HealthCare.com announced the closing of $180 million in an oversubscribed round: $130 million in Senior Non-Convertible Preferred and more than $50 million of Series C Preferred equity, led by funds managed by [Oaktree Capital Management](https://www.edgepedia.org/oaktree-capital-management), with existing investors Axis Capital, Second Alpha, and Link Ventures participating.[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) Trade press reported the round valued the company at more than $1 billion, making it a unicorn.[3](https://www.fiercehealthcare.com/tech/insurtech-platform-healthcare-com-banks-180m-boosts-valuation-to-1b) On February 8, 2022, the company announced an additional $31.5 million in Series C equity from healthcare-focused private equity firm Hildred Capital Management, bringing the total round to $211.5 million; the extension funding was earmarked, per Vargas, for AI and machine-learning investment and possible strategic acquisitions.[2](https://www.hildred.com/news/healthcare-com-extends-previously-announced-financing) • [5](https://refreshmiami.com/news/healthcare-com-raises-additional-31-5-million-extending-its-180-million-round/)
Two figures conflict. The traceable rounds sum to roughly $246 million ($34.5 million before 2021, plus $211.5 million in the 2021-22 round). [CB Insights](https://www.edgepedia.org/cb-insights), an unverified aggregator profile, lists total raised of $253.1 million over nine rounds; that figure rests solely on the aggregator and is not confirmed by the primary press or company announcements.[4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/) • [2](https://www.hildred.com/news/healthcare-com-extends-previously-announced-financing) • [7](https://www.cbinsights.com/company/healthcarecom/financials)
## Business and traction
The company's reported traction is largely self-reported around the 2021 round. It announced direct-to-consumer enrollments up 97% in 2021.[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) Jose Vargas said the company had helped 5.6 million people find and buy a healthcare product in the prior year.[4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/) The over-65 market, about a quarter of the customer base, grew 1,000% year over year, per CEO Don Loonam.[4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/)
Headcount figures differ between the two accounts of the same round. The company's announcement described a distributed workforce of more than 370 employees, up 130% since January 2021, with staff in more than 15 US states plus [Guatemala](https://www.edgepedia.org/guatemala), Thailand, and the Netherlands.[1](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree) Refresh Miami, citing Loonam, reported the team grew from about 100 to 425 employees in a year.[4](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/) The discrepancy is unresolved; both indicate rapid growth from a base of roughly 100. No independent revenue figures appear in the record.
## References
1. [HealthCare.com Raises $180 Million in Oversubscribed Financing Round Led by Oaktree (Business Wire, Dec 13, 2021)](https://www.businesswire.com/news/home/20211213005014/en/HealthCare.com-Raises-%24180-Million-in-Oversubscribed-Financing-Round-Led-by-Oaktree)
2. [HealthCare.com Extends Previously Announced $180M Financing with Additional $31.5M Investment from Hildred Capital (Hildred Capital, Feb 8, 2022)](https://www.hildred.com/news/healthcare-com-extends-previously-announced-financing)
3. [Insurtech platform HealthCare.com banks $180M, boosts valuation to $1B (Fierce Healthcare)](https://www.fiercehealthcare.com/tech/insurtech-platform-healthcare-com-banks-180m-boosts-valuation-to-1b)
4. [Now a unicorn, a Miami insurtech raises $180M round, led by Oaktree Capital (Refresh Miami)](https://refreshmiami.com/news/now-a-unicorn-healthcare-com-raises-180m-round-led-by-oaktree-capital/)
5. [Healthcare.com raises additional $31.5 million, extending its $180 million round (Refresh Miami)](https://refreshmiami.com/news/healthcare-com-raises-additional-31-5-million-extending-its-180-million-round/)
6. [Insurtech platform HealthCare.com secures $31.5m in Series C extension (Life Insurance International)](https://www.lifeinsuranceinternational.com/news/insurtech-platform-healthcare-com-series-c-extension/)
7. [HealthCare.com financials profile (CB Insights, unverified aggregator)](https://www.cbinsights.com/company/healthcarecom/financials)
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*Topic: Encyclopedia › Society and history › Economics and business › Business and work › Business and work overview › Companies and corporations › Venture-backed startups and growth companies › Health, biotech, and medtech startups › Pharmacy, PBM, and health insurance companies*
*Initially written Sep 17, 2026 · Edited: Oct 11, 2026; Oct 15, 2026*
*Copyright 2026 EdgeChat AI, a subsidiary of Biostate AI.*
License: Edgepedia Community License 1.0, https://www.edgepedia.org/edgepedia/license