What Makes Healthcare Law a Strong Career Path for In-House Counsel?

Healthcare law offers in-house counsel a rare combination. Constant regulatory change, high stakes tied to human outcomes, and a dual federal-state framework keep the strategy questions fresh. HIPAA and federal rules govern the delivery of care from above, while 50 state licensing regimes drive the details from below. SimplePractice operates in all 50, so Hartley works both layers every day.

Hartley explains the pull:

"I took my first health law class and I loved every moment of it. I loved the humanity of it, where you can really feel like you're having a contribution towards making health better for people while still focusing on that interest in the law."

She followed the interest through Boston University's health law track, into Reed Smith's health practice, and in-house to Sutter Health. She was always fascinated by medicine, though she knew the science itself was not her path. The law gave her a way into healthcare.

How Do You Set Risk Tolerance Across 50 States?

Hartley's framework separates risk into two categories with different rules. Provider licenses and patient health sit in the first category, where getting people on board with a conservative call is easy, because the downside is a clinician losing a livelihood or a patient being harmed. Business and revenue risk sit in the second, where legal can and should let the company take real swings.

"When you're needing to go a more restrictive route, which isn't always the case, I don't want to imply that we don't take risk and we're not open to risk. But when you're thinking about those two areas, it's easy to influence leaders to understand ... an outcome may impact someone's life in a really negative way, versus a business decision that might have a revenue impact, where you can take a lot more risk."

The practical move that follows is to sometimes take the most restrictive state's standard and apply it across the board, even when no law requires it. The judgment call is knowing which category the decision lives in.

How Did the Pandemic Change Telehealth Law, and How Did Legal Teams Respond?

Two regulatory shifts opened the door for telehealth in 2020. Emergency interstate licensing agreements let providers get licensed across state lines quickly, and Medicare relaxed its rule that a provider needed an in-person visit before billing for telehealth. Providers could suddenly see new patients for the first time over video and get paid for it. Because private insurers follow Medicare's billing guidance, the change moved the whole market.

Hartley remembers the Friday in March 2020 when everyone went home expecting to return in two weeks. By that weekend she had convened a task force across finance, legal, HR, and tech, moving the workforce remote, securing laptops, and working through lease and vaccine policy questions. Then she put on a different hat.

"Don't look at this as just a messy time, which it is, and we need to react to all the things that are happening. But look at it as, where are opportunities also?"

Monitoring the emergency regulations became a project of its own, because each state moved differently, and every change was a new answer to what providers could do and where. The lesson she draws from that year is the one she repeats to younger lawyers:

"Don't wait for permission to do something that you see as an opportunity that can be an unlock or a value add, or a big risk that you need the company to understand. Don't wait for someone to tell you to do it. Do it."

Nobody told Hartley she was in charge of the pandemic response. She looked around, said "I got this," and started. The best legal leaders, in her view, are the ones who take opportunities and run.

How Do You Build a Legal Team the Business Wants to Work With?

Drill one message into the culture until the team can recite it. Legal exists to open opportunities, and the business should come to legal because it wants to, because legal is a problem-solving partner that anticipates issues before anyone else sees them. Hartley has been the first legal hire at more than one company, and she sets that culture before anyone else can set a different one.

"We are not a policing function. We are a business enabler. We open opportunities. We find opportunities. We build relationships across the organization. We are true business partners."

The hard part is unwinding the perfectionism lawyers train into themselves. Hartley names the pattern. Type A perfectionists want to give the perfect answer, tie it up with a beautiful bow, and send it out. That instinct, she argues, holds in-house teams back.

"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."

The leader's half of the bargain is psychological safety. Her team knows that if they push the envelope and something goes sideways, she has their back, and they recover together. Mistakes made while pushing the envelope are evidence of innovation, provided the team admits them, fixes them, and shares the learnings.

How Do Legal Leaders Handle Work-Life Balance?

It looks better from the outside than the inside, and Hartley wants people to say so. She pushes back on the polished image with a story: she brought her son to school without shoes the other day. She rejects the 50-50 idea of work-life balance in favor of mode-switching, leaning into work when it demands it, and taking the afternoon for a kid's game when work eases up.

How Do You Roll Out AI to a Legal Team Without the Fear?

Start with play, before workflows and before demos. Hartley's first AI assignment to her legal team was a creative task on general-purpose AI tools. She had them design a menu for a cafe that blends two worlds, human and underwater, human and steampunk, whatever they wanted. Thirty minutes, no judgment. The outputs ranged from simple menus to a fully coded website, and the team compared results together.

"I was trying to shift from fear to innovation. That's how we think about AI, not as something scary, but as something that helps us innovate."

From there, adoption compounded. Every team meeting now includes a shared AI win, whether that is a manual task automated or an output someone verified and tweaked into their own voice. Her power users teach the rest, including a live demonstration that a chat does not remember your favorite color once you open a new one, which defused the team's data anxiety better than any policy memo. Teams that formalize that education step move faster, which is why GC AI free legal AI courses for legal professionals taught by former general counsels. Full disclosure from the episode: Hartley and her team are GC AI customers, though the cafe exercise ran elsewhere.

The compounding win she cites first is vendor review. Her security team built a prompt that runs the first pass, checking a vendor's history and security posture before a human touches the file, the same first-pass structure in GC AI's guide to vendor agreement review.

"My security team has now built this really awesome prompt for vendor reviews. They're using AI as that first step in a vendor review, to go out and check has that vendor had any cybersecurity events, all these things that previously, I think they told me, used to take between three to six hours per vendor review. And now it's down to less than 30 minutes."

What Should a Legal Team Use AI for First?

Administrative work, deliberately. Hartley's rule is that AI takes the tasks that feel burdensome, and the reclaimed hours go to deep thinking, strategy, problem solving, and relationship building. The human stays in the loop. That means reviewing outputs, confirming sources, and checking the result against a lawyer's judgment.

"I'm really encouraging my team to be human, and let the AI do stuff that feels more administrative and burdensome to you."

How Should Legal Teams Vet AI Vendors When the Data Is Sensitive?

Start from trust and work backward. SimplePractice's customers are therapists whose patients share some of the most sensitive information there is, so Hartley's company-wide AI guidelines sort every use case by task and data type. Public research on non-confidential questions can run on ChatGPT. Anything touching PHI triggers what she calls a laundry list of additional requirements the vendor has to meet, on data use, trust, and even environmental impact.

"Our company needs to be trusted by our customers and by their patients, first and foremost. If we don't have that trust, we don't have a company."

The same filter shaped how SimplePractice launched its first AI product. Her team drafted the terms of service addendum, then put a plain-English summary at the top explaining what the company was committing to, because their customers are therapists, and a reader who cannot parse legalese will fill the gap with worst-case assumptions.

Regulators are moving on the same trust question. Hartley points to the first wave of state law on AI in therapy: Illinois enacted the Wellness and Oversight for Psychological Resources Act in August 2025, Nevada's AB 406 barred AI systems from practicing mental or behavioral healthcare as of July 2025, and New York codified its own AI companion safeguards (General Business Law Article 47, §1700), effective November 2025.

Her position for SimplePractice is clear. Therapy is human-centric, and AI's job is taking the administrative burden off therapists so they can do what they do best.