Article originally appeared on Law360 Pulse.
By: Michele Gorman
For the first decade of her legal career, Carly Duvall Le Riche worked in private practice in Kansas City, Missouri, where a significant portion of her work focused on early-stage companies. She witnessed startups operate without a general counsel and saw other businesses add their first-ever lawyer in that position — as well as the challenges that can accompany the role.
But since she became the first-ever general counsel and head of legal at caregiver support platform Cariloop in June, Le Riche said her experience has been different from what she had seen earlier in her career, she told Law360 Pulse during a recent interview.
“A lot of times when a company is existing before they get their first general counsel, you expect that they’re not as strong on recordkeeping,” she said. “That has not been my experience so far at Cariloop.”
“I get to sidestep some of what I would consider the cleanup, things that a lot of times a first general counsel is doing,” she added.
Le Riche has been in-house since 2021, and her current position at the Dallas-based Cariloop marks her first general counsel role. The company partners with employers to help workers who simultaneously are caregivers.
Here, Le Riche discusses more about the contributions she has made to Cariloop in the past month, how she functions as the sole lawyer there, and what she wishes outside counsel did better. This interview has been edited for length and clarity.
What are some of the challenges that come with being an organization’s first-ever general counsel?
Before I came to Cariloop, and even before I went in-house, I spent about 10 years in private practice working with a variety of companies, focusing on startups and early-stage companies. As outside counsel in private practice, I had seen lots of companies both exist without a general counsel before they got to that stage, and had watched them as they navigated to add their first general counsel. So I had an idea, an expectation of what that would be.
My experience at Cariloop has been slightly different from what I had experienced in private practice. A lot of times when a company is existing before they get their first general counsel, you expect that they’re not as strong on record-keeping. The copies of contracts, the corporate governance documents that you might expect to see — they haven’t done as good of a job of keeping them, maintaining them, organizing them. You also expect that a company wouldn’t have strong controls on things like following process for signatures and permissions for agreements.
That has not been my experience so far at Cariloop. I’ve stepped into a company that has a very strong foundation and structure already in place. I get to sidestep some of what I would consider the cleanup — things that a lot of times a first general counsel is doing.
My organization and my company have given me the blessing of being able to step into a company that has already done those things. I feel like I get to hit the ground running, already contributing to our organization’s mission and growth goals. Even though I am the first general counsel at Cariloop, it feels to me very much like I’m stepping into a role that’s established.
I get to work with my leaders on letting them see the contributions that I can make as general counsel to the company. There might be benefits there for growth that they hadn’t even considered in the ways that I can contribute to their plans.
Obviously there’s the legal function that I’m supporting, but at the end of the day, I’m just another member of the executive team who’s supporting our leadership goals and our mission. Already, I have been able to contribute to those in large part because I stepped into a really good structure.
Can you talk more about the company’s mission?
We are a caregiver support benefit, and partner with employers to provide our solution as an employee benefit. We pair employees caring for a loved one with a care coach who can walk them through a caregiving journey, as well as the digital tools to help them plan and manage their care. Our mission in that is that we’re hoping to relieve the stress and anxiety that is felt by all caregivers. There are all sorts of different types of caregiver journeys people can be on, and they can fluctuate as people go through them; their needs can vary greatly.
We are very proud that our product is broad. We believe that that’s one of the key things that differentiates us in the market — that we’re not just focused on childcare or on the aged population. We’re focused on a lot of different types of individuals who may need help.
What have been your contributions so far?
Already, my role has been incredibly varied. It has to be, because that’s what our product is.
As part of our broad differentiation strategy, we’re looking for ways that we can partner with companies and organizations that are also supporting caregivers so that we can continually offer more robust services to our members. I’ve been working on partnership agreements in that way. We’re gearing up for what is our naturally busy season in Q3 and Q4, so lots of customer agreements and customer renewals. We proudly have a very high renewal rate. That’s certainly a compliment to my team members who work with our members every day.
As I mentioned, it’s really important to us that our product is broad and that we’re meeting all sorts of different caregivers. But we also want to be able to serve as many caregivers as we possibly can. We’re looking at other ways to get our product. Right now, it’s largely through an employer relationship; your employer will pay for Cariloop, and then you get access to the products that way. We’re trying to find other ways to make sure we’re reaching caregivers. I’m already working with our other executive team members on what that might look like. What’s the plan for it?
As general counsel, my job is to advise on regulatory and compliance questions that might come up, information security and data privacy questions that might come up as you navigate that. That’s where I see my contributions — to ask the right questions at the right stages, and then guide them to the right answers.
Are there currently other lawyers on your team?
No, it’s just me. I am a mighty team of one right now.
I had mentioned that in private practice, I had had a lot of experience working with startups and early-stage companies. When I was in that place in my career, I was an extension of my clients’ general counsel.
When you’re one person, you’re the only general counsel, you’re the only lawyer for an organization; you cannot possibly perform all functions. You have to look to outside resources. You have to look to your outside counsel. You have to delegate some things. I have lived that from the other side; now it’s my opportunity to live that being in-house.
Some of the thought and the plan that I put into that is to understand that my job is to strategically lead, guide and be present. My job is not always going to be to actually execute; it may be that I hire outside counsel to actually create the agreement or the document. It’s more important that I leave myself free to have the leadership discussions internally that I need to have.
If we do all the things that we want, if we grow in all the ways that we want to, it won’t be too long before I have the opportunity to expand and add other support members.
When you’re able to grow your department, what traits will you look for in job candidates?
In my general counsel role, I have the legal function and compliance. I’ll talk about the in-house, stereotypical lawyer function that I would add to support me there.
At all times, I care most about someone’s judgment, which is remarkably difficult to assess from a resume and a LinkedIn profile. But those are the kinds of things I’m looking for when I’m having an interview or a conversation. I want to hear about how they handle stressful situations. I want to know what their working style is like. I want to hear how they have navigated complex and layered questions.
Because when you’re in-house, the answers are infrequently “yes” and “no,” and there’s not as many bright lines as you would think. A lot of times, there’s layer and nuance. A lot of times, you find yourself saying, “It depends.” As I evaluate somebody, I want to know how they think through those complex questions. What processes do they use? How do they go about organizing their thoughts around a complicated and long-term, long-ranging-type question?
I know that that’s hard to evaluate, especially when this is a person’s first in-house role. Some of the things that would entice me to a candidate is a broad general experience, not someone who has been siloed, only working on one kind of agreement or in one very specific world. But somebody who can say, “Oh, I have worked on a lot of different types of matters,” or “I have a background in a variety of different areas.” Or even somebody who had a nontraditional path to law, where they have a business background that they’re drawing upon, as well as their legal training. All of those things in a candidate would make me think that this person may have that kind of intangible quality I’m looking for.
You’ve worked both in private practice and in-house positions. Knowing what you know, what’s one thing you wish outside counsel did better?
One of the challenges I find with my outside counsel sometimes is that they tend to believe that our decision making exists in a vacuum — and it does not. What I mean by that is I might reach out to outside counsel and ask them if some aspect of our communication is permissible in a certain jurisdiction. Or I might ask them to provide me guidance in a particular jurisdiction. Often, what I will get back is just a black-and-white answer.
What I’m actually looking for is more of an answer that recognizes that things exist on a spectrum; an understanding where they say, “Well, here’s one way you could go about it. It is less risky, but it may take you longer to grow in that jurisdiction if that’s the way that you go. On the other hand, there’s another route that is slightly more risky. But if you’re willing to accept those risks — and here I’ve spelled them out for you — here’s another path to go forward.” That’s one of the things I wish they understood more.
The other thing I think is that they don’t always appreciate the timing that in-house decisions are made. A lot of times, their feedback will allow me as general counsel to guide on timing. I think they think of it as a black-and-white, yes/no. I think of it more like, “Well if you just tell me it’s a harder thing to do, then that just means it takes me more time to get there, and that’s OK.” That could be the advice.
I think my really good outside counsel have the ability to communicate on that risk continuum spectrum and understand a lot of our decisions are made in a push-pull fashion and guide me in that way. I always appreciate that approach.
What’s one of the biggest challenges of navigating the general counsel role in 2024?
It is a very broad role. In some ways, I think that’s wonderful for the legal profession and for the clients whom we are supporting. My role specifically includes not just the legal function, but it includes a compliance function. I think all general counsel, regardless of the industry, will tell you that they necessarily have to understand things like data privacy and information security as part of their role. That wasn’t something that was present as strongly 10 or 15 years ago. But it is certainly a key part of our function now.
Those are really broad and different categories of things that you manage. I have to wear different hats. Sometimes I have to wear my business hat. Sometimes I have to wear my lawyer hat. I feel like we just keep stacking different hats on top of the general counsel role. Sometimes you have to put on your compliance officer hat, and sometimes you have to put on your information security officer hat.
I think that breadth is one of the challenges that certainly I have, as well as other general counsel.
What’s one thing you know now that you wish you had realized earlier in your career?
I have spent 15 years in practice, and I’ve pretty much always been a generalist, in that my practice has always been very broad. I’ve done a lot of different types of work in a lot of different types of industries.
I would love to tell you that I did that with intentionality in 2009 when I graduated law school, and that I intentionally guided myself that way. But that is not the case. I stumbled into that. A variety of circumstances led me down that path.
Where I sit now, I am so happy that that is the background and the training that I got early in my career. I am so happy that I got a lot of different experiences like that. Certainly, it has been phenomenal training for a general counsel role. But beyond that, I think it in general has made me a much better lawyer.
If I were to go back in time and talk to that very young lawyer coming out of law school, who was very nervous, I would say, “You’re doing the right thing. Keep doing it. Learn as much as you can about as many different things as you can, and it will make you a much better lawyer in the end.”
What’s a fun fact about you?
I am certified to teach yoga. I don’t teach very much right now. I’ve been a little bit too busy for that. But I love it. And as a practitioner, I take yoga classes for my own mental and physical well-being.