Trent Haywood
Angel investor in Chicago
Chicago, Illinois
Trent Haywood, Angel investor in Chicago is an active investor based in Chicago, Illinois. This profile covers what Trent Haywood backs, at which stage, and how founders can reach out in 2026.
Dr. Trent Haywood serves as Board Member at Healthmap Solutions. Dr. Haywood is a leading healthcare executive who has been at the forefront of the healthcare industry's transformation to value-based care and whose expertise in developing and leading best practices to improve quality, drive clinical innovation and eliminate social determinants of health barriers to care has earned him industry-wide recognition. He is a board-certified internal medicine physician who brings over 20 years of healthcare management experience to the Healthmap Board. Trent is the founder of KNOWALITY, LLC, a venture services firm dedicated to accelerating the market adoption of innovative healthcare services and products that improve population health. Most recently, Trent served as Chief Medical Officer of the Blue Cross Blue Shield (BCBS) Association, where he was responsible for guiding medical policy and clinical programs for the association's 36 member health plans. In addition, he served as President of the Blue Cross Blue Shield Institute, a benefit corporation focused on addressing the social determinants of health for BCBS plans. Previously, he led national efforts to implement value-based healthcare as Chief Medical Officer at Vizient (formerly VHA, Inc.) and Deputy Chief Medical Officer for the Centers for Medicare & Medicaid Services (CMS). He earned a medical degree from the University of Illinois at Chicago and a Juris Doctor degree from Northwestern University. Trent is a graduate of Notre Dame University, where he earned a Bachelor of Science degree. He is an Angel Investor.
- Investor type
- Angel
- Stages
- Early Stage Venture
- Invests in
- FintechPaymentsInsurTechHealthcare & BiotechDigital Health & HealthTechSaaS & EnterpriseConsumer & RetailE-commerce & D2C
- Location
- Chicago, Illinois
- Typical check
- $500K
- Past investments
- 2
Notable investments
RulaHow to reach Trent Haywood
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Round Funded. "Trent Haywood." Round Funded investor database, updated September 8, 2026.
Stable URL, it will not change: https://www.roundfunded.com/en/investor/trent-haywood
Frequently Asked Questions
What does Trent Haywood invest in?
Trent Haywood invests in Fintech, Payments, InsurTech and Healthcare & Biotech, typically at Early Stage Venture. Match your sector and stage, then reach out with a personalized pitch.
What stage does Trent Haywood invest at?
Trent Haywood typically invests at Early Stage Venture. Lead with traction that fits the stage when you reach out.
What is Trent Haywood's typical check size?
Trent Haywood typically writes checks around $500K. Use it as a signal for whether your raise fits their stage.
How do founders reach investors like this?
Round Funded lists active investors with verified, professional contact details for signed-up founders. Filter by sector, stage and location, then send a personalized pitch from your own inbox.
What is Round Funded?
Round Funded is an investor database and outreach platform for startup founders. It lists 60,000+ active investors with verified contacts, filtered to recent investment activity, and lets founders send personalized pitches from their own Gmail, track replies, and share a free Data Room. Round+ starts at $99 per month with a 3-day trial.