Music lovers take note: A new pair of headphones on the market will test your hearing — courtesy of a digital assistant that greets you upon activation — in order to pump high-definition sound into your eardrums.

At a time when headphone manufacturers are elevating their technology game to compete against one another, Israel-based startup EVEN last week pulled back the curtain on the H2, a pair of Bluetooth headphones.

These aren’t just any ordinary music players, however: The $299 wireless headset administers an on-the-spot hearing test, powered by interactive software that tailors the listening experience to an individual’s hearing. Sarah — a very Siri-esque virtual assistant — walks the user through the process, and chimes in every time the H2 powers on.

The end result is a personalized listening session that sounds distinct for whomever is wearing the H2 — based largely on what EVEN euphemistically calls an “EarPrint” that is as unique as a fingerprint. To date, EVEN has raised $4 million in seed capital, and is targeting the completion of another round worth an additional $6 million, the firm’s CEO told CNBC in a recent interview.

“Our technology gives people a listening experience that they may have never had before or have not heard in a long time,” said Danny Aronson, co-founder and CEO of EVEN. “We make it possible for people to re-discover music and hear what they’ve been missing.”

Audiophiles might either be charmed or put off by the EVEN H2’s throwback exterior, constructed as it is from eco-friendly wood ear cups and vegan leather trim that collapses into a more portable size. It resembles something that appears more appropriate for the era of 8-tracks and turntables, and it facilitates full playback control but can be somewhat clunky when worn.

And despite the pleasant voice of Sarah, the intelligent assistant that powers the H2, a unit tested by CNBC came with a small drawback: The H2 had to be manually synced to the device each time it was powered up, rather than connecting automatically.

Yet the headphone’s vintage look obscures the very high-fidelity sound that resulted in having the H2 take the listener’s EarPrint—something that can be fully appreciated when allowing another person to create their own listening profile, then playing music through their (virtual) ears. The user’s listening profile is collected and stored in a mobile app that shows the listener their EarPrint, and monitors the H2’s battery life.

It’s part of Aronson’s long-term strategy to make EVEN’s EarPrint a staple that can be used in other wireless speaker and headphone makers.

“EVEN is actively engaged in licensing its technology — since, uniquely, EVEN is a technology company, not specifically a headphone or HW company — and has secured licensing contracts in several audio verticals in the personal audio space not limited to headphones,” Aronson told CNBC in an email. He declined to comment on which ones, as talks were still ongoing, but said there were “quite a few.”

The H2’s value proposition is being made in a marketplace where wireless headphones are becoming more high tech. Sensor-enhanced artificial intelligence is boosting the music listening experience, and even helping users manage their homes and perform other tasks.

“The use case for headphones goes beyond audio,” Ben Arnold, a consumer technology analyst at NPD Group, told CNBC recently. He says sensor-enhanced headphones are called “hearables,'” a new category of headphones that do far more than just stream music.

–CNBC’s Mike Juang contributed to this article.