Dan Cimaglia
Thanks for visiting my site. I'm from New Jersey, live in NYC, and have spent most of my career in payer partnerships at Headway, a company expanding access to mental healthcare.
Outside of work, I enjoy improving my Italian, travelling, and exploring the city. I also advise, consult, and occasionally invest in early-stage healthcare startups.
Georgetown University – McDonough School of Business
Georgetown McDonough Alumnus Improves Mental Health Accessibility Through Headway Platform
Read at msb.georgetown.edu ↗
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Experience
Behavioral health
Various ops/strategy, payer, and GTM roles, Chief of Staff · 800+ employees, $2.3B valuation (started as ~#20, $75M)
Some of my favorite projects:
- Led Headway's national expansion
- Led strategic portion of Headway's Series C, bringing HCSC, BCBSMA, and a national payer onto the cap table, and helped craft the payer narrative for our Series B and D raises
- Signed 45 payer contracts (commercial + gov't programs) in <18 months
- Launched Headway's newest business line, health system partnerships
Senior care
Had the opportunity to lead health system partnerships for a senior care management startup, but realized my time at Headway wasn't quite done yet. Went back after five months.
Commuter parking and drive-in movies
Originally joined to grow our "Airbnb for commuter parking" model, but pivoted into drive-in movies and grocery delivery during the pandemic to stay afloat.
Georgetown University, McDonough School of Business
Finance major, Psychology minor
Advising & Investing
Startup advising and consulting
Using my experience from five-plus years at Headway, I advise and consult for healthcare startups. I typically help founders with payer strategy, ops and credentialing, fundraising, or anywhere else I can be useful. I've seen a lot (good and bad) scaling Headway from ~$XM to ~$XXXM in revenue.
Investing
I work with DHVP, a venture firm I scout for and advise. The firm is led by Arvin Grover and Steve Yaskin (founder of Health Gorilla). They've built an impressive portfolio, and it's been great supporting their work.
Outside of DHVP, I occasionally invest personally — often with founders I've met through my own consulting and advising work.
If I can be helpful from an advising or fundraising angle, don't hesitate to reach out. Even if not, I'd still love to connect — I really enjoy meeting founders and teams working on interesting problems. You can reach me at loading.
Companies I've worked with
- Assured Health seed investor
- Oasys investor and advisor
- Simbie
- Pom Health
- Big Leap Health
Beyond Work
Outside of work, I spend a lot of my time learning Italian. I'm currently at a B2–C1 level (conversational) and am documenting the journey on my Substack.
Contact
Feel free to reach out using the form below, connect with me on LinkedIn, or email me at loading.