Ali Hartley has spent most of her career leading legal operations at large health organizations like Sutter Health, Nurx (formerly Pill Club), Carbon Health, and now SimplePractice. She was drawn to this unique speciality before she even entered law school because of the potential to use the law to improve lives.
“I took my first health law class when I was in law school at Boston University and I loved it,” she said. “I loved the humanity of it where you can really feel like you're contributing towards making health better for people while still sort of that focusing on that interest in the law.”
After earning her JD, Ali spent nearly a decade building her health law chops at Sutter Health. She then moved up to CLO in an industry where the legal stakes affect actual patient care, provider livelihoods, and the consumer trust that holds the whole American healthcare system together.
Along the way, Ali has navigated the Affordable Care Act, a global pandemic, the telehealth revolution, and now AI. Turns out, healthcare law is anything but boring. Much of her job involves understanding how state and federal regulations apply to healthcare companies like Simple Practice, but her biggest priority as CLO is to think like a business operator.
“In-house legal is not a policing function,” Ali said. “We open opportunities. We find opportunities. We build relationships. We are true business partners."
What Makes Healthcare Law an Exciting Career Path
The question constantly on Ai’s mind is this: how do you take the most restrictive state codes and apply that standard everywhere, even when you're not legally required to? Her answer depends entirely on what's at stake.
Healthcare law sits at the intersection of a sweeping federal framework, including HIPAA, CMS guidance, and Medicare billing rules, and 50 separate state licensing frameworks, each with its own fine print about where and how providers can practice. Simple Practice operates in all 50 states, meaning there’s a lot of complexity in Ali’s day-to-day.
“I always feel like I have job security because it's a constantly changing, and very complex field,” she said. “What I think is so interesting about it is you have both a federal framework, when you think about HIPAA and some other sort of federal laws that oversee the delivery of healthcare, but at the same time, so much of it is driven at the state level.”
Risking provider licenses or patient health is a nonstarter. For Ali, making the wrong call means someone loses their license or a patient is seriously harmed. Revenue risk is a separate calculation entirely, and one where she pushes her team to hold more often than not.
A Global Pandemic as a Crash Course in Legal Leadership
In March 2020, Ali was sitting in her office on a Friday afternoon when the company quietly decided nobody was coming back to work the next week. Like everyone else, Ali had assumed the COVID-19 pandemic would be over within a couple of weeks. It wasn't.
What happened next is a great example of how a great CLO operates under pressure. While most of the business was still reeling, Ali was asking an important question: where are the opportunities for us here?
"Don't look at this as just a messy time,” Ali said. “Look for the opportunities, too."
That weekend, she convened a cross-functional task force that included finance, legal, HR, and tech. They began the process of moving an entire workforce off-site, securing laptops and remote access, navigating lease obligations, figuring out new vaccine policy. But during all of that, Ali was also tracking another opportunity: the emergency regulatory changes that were quietly opening new doors in healthcare.
Medicare guidelines used to require an in-person visit before a doctor could bill for a telehealth appointment. But in March 2020, that rule was relaxed almost overnight. Suddenly providers could see new patients for the first time over video and get paid for it. Telehealth companies like Ali’s had a massive opportunity, and fortunately their CLO was ready to move right away.
“If I could tell younger lawyers something, it would be this: don't wait for permission to do something that you see as an opportunity to add value or to flag something that you think is going to be a big risk,” Ali said. “Don't wait for someone to tell you to do it. Just do it.”
Note from CZ: The instinct to look for the opportunity in chaos is also what brought David Morris to the Cuba finish line and Kerrie Forbes to a successful relationship with Orange County Airport. The best in-house lawyers mine regulatory opportunities for the company’s benefit. Ali turned one of the most chaotic moments in modern history into a growth unlock for her organization.
Building a Legal Team Your Leadership Wants to Talk To
Ali has been the first legal hire at multiple companies, and every time she is quick to establish the team culture before anyone else does. Her philosophy is to become the partner cross-functional leaders want to bring in at the beginning, rather than a box to check at the end.
That sounds simple enough, but getting there means convincing lawyers who were trained for precision and perfection to get comfortable with ambiguity, take initiative, and yes, mess up a few times.
"Don't be afraid to make mistakes,” Ali said. “The best lawyers are not the ones who don't make mistakes. They're the ones who make mistakes, recover from them quickly, and learn from them."
A large part of building a culture that tolerates learning from mistakes is psychological safety. Ali’s team knows that if they push the envelope and something goes sideways, she always has their back. Lawyers love having all the answers, but the best in-house lawyers focus on building trust first.
Introducing AI Tools Without Fear
Ali decided to approach the AI shift a little differently than most business leaders. Instead of beginning with workflows or demos, she gave her team a simple creative prompt: design a menu for a cafe that spans two completely different worlds. It could be steampunk and human, underwater and terrestrial, whatever they wanted. She asked them to spend 30 minutes on it and have fun, without judgement.
The outputs ranged wildly. A few people submitted basic menus, while another built an entire website, complete with back-end code. The point of this exercise was for each team member to rethink how they perceived AI and its limitless possibilities.
"I was trying to shift from fear to innovation,” Ali said. “How do we think about AI not as something scary, but as something that helps us innovate?"
From there, Ali built a standing “AI Wins” segment into every team meeting. Each week, they take turns showing off how they’re using automation to save time on tedious tasks. One great example is the security team's vendor review process. What previously took three to six hours per vendor now takes under 30 minutes, thanks to a new AI workflow.
“I've been really very deliberate about using AI for administrative tasks so my team can free up their human minds, right?” Ali said. “Then they can use that time to do more deep thinking, more strategy work, more problem solving, and relationship building. I'm really encouraging my team to be human.”
Ethical Leadership and Building Trust in Healthcare AI
For healthcare-adjacent companies like SimplePractice, trust is part of the product. The platform’s customers are therapists whose patients share some of the most sensitive information available. This means that onboarding any new software is a risk, and choosing the wrong AI vendor could mean a betrayal of very vulnerable customers.
"If we don't have that trust, we don't have a company,” said Ali. “When you start there and you are building customer protections into the product, it’s a lot easier over time because everyone's on the same page."
When Simple Practice launched its first AI product, Ali’s team decided to add a plain-English summary at the very top of the page explaining what the company was committing to in language a therapist (rather than a lawyer) would understand.
“Therapy is human-centric,” said Ali. “Our goal is to take the administrative burden off of therapists so that they can do what they do best. AI can be a very powerful tool to help drive that human-centric interaction between patients and their therapists.”
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