Insurance technology · Medicare distribution
Medicare Vox
A San Francisco Medicare brokerage that spent five years selling insurance to seniors, then turned the call center itself into an AI product. In January 2026, the parent company was bought by an Omaha insurance marketing organization, and the AI agent is what it is now known for.
The phone call that never puts you on hold
The pitch, in the company's own words: a senior calls to arrange a ride to a doctor's appointment. Instead of a twenty minute wait and five transfers, an AI voice agent asks where they are going, books the car, and tells them when to expect it. Three minutes, done.
That scenario comes from the company's own about page, and it captures what Medicare Vox is trying to sell now: not a brokerage, but software that other brokerages and carriers can use to run their call centers with fewer humans on the non licensed parts of the job.
The problem it started with
Medicare has roughly 50 plans a new enrollee can choose from, according to the company's own account of its founding, and a Kaiser Family Foundation study cited in its funding announcements found that nearly 60 percent of Medicare enrollees don't review or compare their coverage options annually. Most people lean on a broker, and brokers are usually paid by commission, which the company argued creates an incentive to sell the plan that pays best rather than the plan that fits.
More than 10,000 Americans turn 65 every day. That volume is the whole business case: a large, recurring population that needs help making one high stakes decision a year, plus ongoing help using the benefits once enrolled.
A founder who had seen the system fail his parents
Daniel Petkevich founded Fair Square Medicare in 2019. He has said in multiple interviews that the idea came from watching his own parents, immigrants from the former Soviet Union, struggle with Medicare enrollment, speaking to ten different local brokers before finding one they trusted. Separately, his mother could not find usable provider quality data before a knee replacement and delayed the surgery, and his father waited months for an MRI on a slipped disc, according to a 2022 Forbes account.
Before Fair Square, Petkevich co-founded Trim, later acquired by OneMain, and Octane Lending, which the company's own team page describes as reaching a 1 billion dollar valuation; both claims come from company published bios rather than independent reporting. He studied physics at Yale, per the same source.
From brokerage to Series A to AI platform
Fair Square Medicare went through Y Combinator's Winter 2020 batch. By August 2022 it had raised a 15 million dollar Series A led by Define Ventures, with Slow Ventures, Y Combinator and angel investors participating, bringing total funding to 19 million dollars by the company's own account. Amplo is also named as a backer in company materials. At the time the company operated in 49 states and Washington, D.C., and reported a 90 to 94 percent annual customer retention rate against an industry figure it put at 50 percent.
Two years later, in August 2024, the company launched Vox: a generative AI platform built on GPT-4, with an AI voice screening agent named Sophia as its first release. The company said Sophia matched human agents' sales conversion during business hours and beat them four to one on after hours calls. By late 2024, coverage of the launch described the whole company's cumulative funding as 15 million dollars across two rounds, a lower figure than the 19 million dollars the company itself had cited in 2022; no source explains the gap.
The rebrand followed: Y Combinator's own company page now lists the business as "Medicare Vox (fka Fair Square)," and the company's website, medicarevox.com, presents Vox as the product and Fair Square as the brokerage arm that built it.
Bought by an insurance marketing organization
In a release dated January 30, 2026, Senior Market Sales, an Omaha based insurance marketing organization owned by Alliant Insurance Services, announced it had acquired Fair Square Medicare. SMS President John Haver said the deal brought Daniel Petkevich and his team into the SMS family, and Petkevich, quoted as Founder and CEO of Fair Square Medicare, said joining SMS and Alliant would let the company "supercharge" its mission. Neither company disclosed terms. No SEC filing or other public record naming a purchase price was found.
What is proven, and what is still claimed
| Evidence | What the record shows | Source type |
|---|---|---|
| Founding and founder | Daniel Petkevich founded the company in 2019; it went through YC Winter 2020. Confirmed across company materials, YC's own listing, and independent press from 2022 through 2024. | Public record |
| Series A | 15 million dollars, led by Define Ventures, announced Aug 25, 2022, reported consistently by Forbes, Fierce Healthcare, San Diego Business Journal and PR Newswire. | Independent |
| Total funding | Company said 19 million dollars to date in Aug 2022; a 2024 directory item put lifetime funding at 15 million dollars across two rounds. No SEC Form D was found for the company under any name searched, so neither figure can be checked against a filing. | Conflicting figures |
| SEC Form D | EDGAR full text search returned zero hits for "Fair Square Medicare," "Fair Square," and "Medicare Vox" among Form D filings as of Sep 25, 2026. | Not found |
| AI performance claims | Company says its Sophia voice agent matches human agents during business hours and converts four times better than the typical after hours process. No independent study or audit of these figures was found. | Company-stated |
| Customer counts | Reported at different points as "in the high thousands," "15,000 seniors," and "tens of thousands," each from a different company statement between 2022 and 2024. | Company-stated |
| Headquarters | PR Newswire's 2022 release lists San Diego; the San Diego Business Journal lists Carlsbad; PR Newswire's 2024 release and Y Combinator both list San Francisco. | Differs across releases |
| 2026 acquisition | Senior Market Sales, an Alliant Insurance Services subsidiary, announced it acquired Fair Square Medicare on Jan 30, 2026. Terms were not disclosed. | Company release |
Read plainly: the business itself, its founder, and its Series A round are well documented by independent outlets. Everything past that, including the size of the AI performance gains, the exact customer count, and even the city the company calls home, comes only from the company's own statements, and those statements don't always agree with each other.
What to watch
- How Medicare Vox operates inside Senior Market Sales and Alliant. No integration details or new leadership structure had been published as of September 2026.
- Whether an amended or new SEC filing ever surfaces for the company, since none has been found under any name tested.
- Named, independently verified results for the Sophia voice agent beyond the company's own after hours conversion claim.
- Whether the Vox platform is sold to other carriers and brokerages beyond Fair Square's own book of business, which was the stated goal of the August 2024 launch.
In their words
“I wanted to build the brokerage that I wish my parents had - a customer-obsessed, tech-enabled firm that makes plan recommendations regardless of commission,”
Daniel Petkevich, founder and CEO, to Forbes, Aug 25, 2022 · Independent
“Most brokers live off commission and often will steer people to the wrong Medicare Advantage plan that doesn’t fit their risk preference or doesn’t cover their doctor or prescriptions.”
Daniel Petkevich, to Forbes, Aug 25, 2022 · Independent
“Seniors deserve a trusted healthcare partner that’s always acting in their best interest.”
Chirag Shah, Partner, Define Ventures, PR Newswire, Aug 25, 2022 · Investor
“I saw firsthand how broken the entire enrollment experience is when my own parents approached Medicare eligibility. They deserve much better.”
Daniel Petkevich, PR Newswire, Aug 14, 2024 · Company release
“Using AI, our Vox platform unlocks 10x outcomes for Medicare distributors and carriers and provides a superior experience for customers much more cost effectively.”
Daniel Petkevich, PR Newswire, Aug 14, 2024 · Company release
“Fair Square Medicare has successfully built a model that combines the efficiency of technology with the empathy of personal service.”
John Haver, President, Senior Market Sales, Jan 30, 2026 · Company release
“We started Fair Square with a mission to build a comprehensive care navigator that seniors can trust for the rest of their lives,”
Daniel Petkevich, Jan 30, 2026 · Company release
“Seniors deserve better. Seniors deserve a broker that treats them as they would their own parents.”
Company about page, medicarevox.com, accessed via archive Sep 2026 · Company-stated
Related companies
Sources
- Public recordMedicare Vox (fka Fair Square) company page
- IndependentFair Square Medicare Just Raised Its Series A
- IndependentFair Square Medicare secures $15M to build out digital care navigator for seniors
- IndependentFair Square Lands $15M Series A
- IndependentFair Square Medicare Unveils Generative AI Platform for Medicare Organizations
- IndependentIntroducing Vox by Fair Square Medicare
- Public recordSEC EDGAR full text search, no Form D results for company name variants
- IndependentFair Square Medicare BBB business profile listing
- CompanyFair Square Medicare raises $15 million Series A to build comprehensive care navigator for seniors
- CompanyFair Square Medicare Launches Generative AI Platform that Transforms Customer Experience for Medicare Entities
- CompanySenior Market Sales Acquires Fair Square Medicare, Expanding Digital Capabilities in Senior Health Care
- CompanyMedicare Vox about and team page
Profile researched and written by Healthcare Discovery. Last updated September 29, 2026.
