About
About Hindsight
Hindsight is an open-enrollment records service from Triangle that assembles last year's care from your medical records so you can look back before comparing health plans, for anyone picking a plan this enrollment season.
Start your 7-day free trial7-day free trial, then $9 a month. Cancel anytime.
What Hindsight does
Your year in care, from your records
Hindsight sends for your records over Carequality and TEFCA, the national networks, and turns them into a current history of your year. Ask how many specialist visits you had, which prescriptions you fill each month and what tests were done.
Plan summaries, talked through
Upload each plan's summary of benefits as a PDF. The chat talks through what it says next to the care you actually used.
Prescriptions and gaps
Prescriptions show up with their pharmacy fills when the records hold them. Where your year looks thin, Hindsight flags it and helps you send for the missing records.
Choose together
Share your profile with a spouse or family member who is weighing the options with you. Nobody else sees it unless you say so.
What makes Hindsight different
It starts from your own year
A plan summary lists copays, deductibles and drug tiers, and reading one well takes your own history of care. Hindsight assembles that history from your records rather than from receipts and memory.
Records, not a spreadsheet
A spreadsheet of visits and prescriptions holds whatever you remember to type in. Hindsight builds the picture from what your doctors recorded at many hospitals and clinics.
Plain about its limits
Hindsight doesn't recommend a plan, check networks, estimate costs or read bills and claims. For advice on choosing, a licensed broker or your employer's benefits team is the right place to go.
Count visits from the assistant you use
Connect Claude, ChatGPT or Grok, and with your permission it can read your visits, prescriptions and test results while you compare plans. Disconnect it whenever you're done.
Only as long as you need it
A card starts the 7-day free trial, and from there Hindsight costs $9 a month. If you only need it for this enrollment season, cancel in whichever month suits you.
Who uses Hindsight
- People comparing health plans during open enrollment
- People who see a specialist regularly and want to ask each plan about that doctor
- People who fill prescriptions every month and want them in view when they compare drug tiers
- Couples and families choosing a plan together
The team behind Hindsight
Triangle (Triangle Health, Inc.) builds Hindsight in Pasadena, California, for people who'd rather choose a plan with the facts of their own year in front of them. Triangle started with a look back of its own: after a brain tumor diagnosis in 2023, Arun Verma researched his care by hand, then co-founded the company as CEO with Jonathan Grubb, formerly of Bird and OpenTable, and Justin Balthrop, a Bird co-founder. Hindsight makes that research a service anyone can use, including people taking stock of a year of care before open enrollment.
- Arun Verma, Co-founder and CEO · arunverma.io · LinkedIn
- Jonathan Grubb, Co-founder · LinkedIn
- Justin Balthrop, Co-founder · LinkedIn
- Dr. Santosh Kesari, Founding medical advisor, neuro-oncologist
How Hindsight works
Open your trial
Start Triangle's 7-day free trial with a profile for yourself, and say yes when it offers to connect your records.
Verify, sign, book
Next comes the paperwork, which covers proof of identity, your address, signed consents and a booked intake visit with a clinician.
Your year comes together
Triangle asks the national networks for your records, and the plan summaries and anything else you have, you upload. After that, go over your health topics and prescriptions, ask about the year, and let a spouse in if you're choosing together.
Ask from your assistant, if you like
Connect Claude, ChatGPT or Grok to count visits from the chat you already use. If setup trips you up mid-enrollment, Triangle is at support@trianglehealth.com.
Key facts about Hindsight
| Name | Hindsight |
|---|---|
| Made by | Triangle (Triangle Health, Inc.) |
| Type | Health records and AI service for open enrollment |
| Core offering | Your past year of care, gathered from your records, to review before you compare health plans; Hindsight does not recommend plans, check networks or read bills. |
| Who it's for | People comparing health plans during open enrollment; People who see a specialist regularly and want to ask each plan about that doctor; People who fill prescriptions every month and want them in view when they compare drug tiers; Couples and families choosing a plan together |
| Founders | Arun Verma (CEO), Jonathan Grubb and Justin Balthrop |
| Medical advisor | Dr. Santosh Kesari, neuro-oncologist |
| Started | After co-founder Arun Verma's brain tumor diagnosis in 2023 |
| Headquarters | Pasadena, California, United States |
| Funding | $4 million pre-seed round, announced March 2026 |
| Website | www.hindsightplans.com |
| Pricing | 7-day free trial (card required), then $9 a month |
| Contract terms | Month to month; cancel any time |
| Works with | Claude, ChatGPT, Grok and other assistants that support MCP (setup guides) |
| Support | support@trianglehealth.com |
| Privacy and security | HIPAA compliant · Trust Center |
| Social | LinkedIn · Instagram |
Frequently asked questions
Who makes Hindsight, and how does it help at open enrollment?
Hindsight gathers your records so you can see the care you actually used before you pick a plan. Registration happens with Triangle, the company that makes it, at trianglehealth.com.
What will Hindsight cost for open enrollment?
Hindsight asks for a card when your 7-day free trial begins. Afterward the price is $9 a month; cancel when you like, and a cancellation before day 7 carries no charge.
Does Hindsight give medical advice, like a doctor?
No. Like everything Triangle makes, Hindsight stops at research and educational support: no diagnosis, no treatment, no prescriptions. Your clinicians decide on your care, just as you decide on your plan.
While I compare plans, could my ChatGPT, Claude or Grok look at the year Hindsight put together?
Yes. Give the assistant https://app.trianglehealth.com/mcp, Hindsight's MCP connector, then decide on Triangle's consent screen how much of your year it can see; each assistant's setup steps are spelled out at trianglehealth.com/agents.
Is my year of care kept private and secure?
Triangle, which is HIPAA compliant, holds your year of care encrypted in transit and at rest. Your records aren't for sale and aren't shared for advertising, and you control who sees your profile.
Will Hindsight tell me which plan to choose?
No. It shows you your own care and talks through the plan documents you upload, and the decision is yours. A licensed broker or your benefits team can advise.
Can it check whether my doctors are in network?
No, and it doesn't read bills or claims. Your records show which doctors you saw, so you know whom to ask each plan about.
Will my insurer see any of this?
Not unless you choose to share it with them. Hindsight shows your profile only to the people you pick.