Will Jones
How a Chicago healthcare regulatory attorney turned an unconventional career path into a platform for the next generation of lawyers
When a state passes a new health insurance mandate, the language does not enforce itself. Someone has to read the statute, work out what it actually requires, and translate it into language that members and regulators will eventually read. That quiet, exacting work tends to happen far from any headline. At one of the largest health insurers in the country, a lot of it runs through Kairvi Tijoriwala.
Kairvi is a health insurance regulatory attorney, and since the middle of 2023 she has been one of the people responsible for turning newly enacted state mandates into something real for the millions of members. It is not glamorous on paper. It is also the kind of work that ensures coverage requirements are accurately reflected in plan documents, whether a marketing claim is accurate, and whether an insurer is actually doing what the law tells it to do.
The Work Most People Never See
Ask most people what a health insurance lawyer does and you tend to get a blank look. Kairvi sits at the point where policy becomes practice. She reviews the filings her company submits to the state regulatory agency, and she serves as one of the legal contacts with that department. When a new mandate arrives, she advises the teams who have to act on it on how to comply with the new law: medical directors, product leads, and the communications staff who write the material members and providers eventually read.
That last piece matters more than it sounds. Kairvi reviews customer facing and provider facing material, the documents that explain what a plan covers. A single careless sentence in that material can mislead a member about their own benefits. Her job is to make sure the language on the page matches the rule in the statute.
The scope is wide. Her work shapes the regulatory framework that governs coverage for millions of people across the state, most of whom will never know her name. That is the nature of regulatory work. When it is done well, nothing dramatic happens. The system simply functions the way it is supposed to.
A Career Path Built Sideways
What makes Kairvi interesting is not only what she does now but how she got here. Her route into health insurance law did not follow the script.
She started in tax at a big four accounting firm. There she advised on international mergers and acquisitions, corporate restructurings, and tax planning for companies operating across borders. From there she moved to one of the largest law firms in the world. There she worked on mergers and acquisitions, joint ventures, and deals that took public companies private.
Then she moved in house.
Big Four to BigLaw to regulatory counsel is an unusual sequence, partly because she began in the Big Four world after law school rather than before it. Many lawyers treat their first job out of school as a fixed destiny. Kairvi treated each stop as preparation for the next, carrying her tax and transactional training into a regulatory role that draws on all of it.
Turning the Curtain Back
Plenty of accomplished attorneys keep their heads down. Kairvi does something less common. She talks openly about the messy, nonlinear reality of building a legal career, and she does it where young lawyers actually spend their time.
On Instagram and TikTok she creates content for law students and attorneys early in their careers, with a focus on people arriving from unconventional backgrounds. The message is steady and useful: there is no single correct way into the profession, and a winding path can be a strength rather than a liability. For students who do not see themselves reflected in the traditional pipeline, that is a rare and reassuring voice.
It also reflects how she works. The same instinct that drives her to render dense regulation into plain guidance for her colleagues shows up when she explains the profession to strangers online. She is, in both settings, a translator.
Recognition and What Comes Next
The field is starting to notice. Kairvi is currently being considered for Law Bulletin Media 40 Under Forty and Bloomberg Law 40 Under 40, along with other emerging leader honors. She has served as a judge for the ABA Client Counseling Competition, and she sits on the 2026 Communications and Publications Committee of the IAHA.
She is also writing. Kairvi serves on the 2026-2027 Editorial and Content Board of TYL, the American Bar Association Young Lawyers Division’s flagship publication, which publishes legal content for early-career attorneys nationwide.
For now, Kairvi keeps doing the work that rarely draws applause. She reads the statutes. She reviews the filings. She answers the state. And in between, she tells the next generation of lawyers that the path does not have to be straight to be worth taking.