At Pearl Health, there are a lot of moving pieces — from product development to patient outcomes, customer support to clinical strategy. That’s where Ciara Walsh comes in. As Chief of Staff, she connects dots across the organization, helping to turn strategy into execution and keep everyone moving in the same direction.
In this conversation, Ciara shares her thoughts on the value of transparency, the power of cross-functional collaboration, and why doing meaningful work often starts with having a plan (and perhaps a good amount of chocolate).
What do you do at Pearl? How would you describe your role to others?
Mike [Pearl’s CEO] and I work closely across all areas of the business – ensuring strategic alignment, prioritization and focus, – while removing obstacles and driving clarity to maximize team performance. I’m in conversations across teams, so I can see how seemingly unrelated projects actually fit together. It’s like solving a puzzle every day — and I love that.
I am also very fortunate to manage the People, Marketing, and Executive Office teams so those worlds have an extra special place in my heart! And they come together in a powerful way: aligning our internal and external brand creates an authentic voice that is based in our values and strategy. I love working with my teams to ideate, solve problems, and make a difference.
What brought you to Pearl in the first place?
Without a shadow of a doubt, it was the people. Mike [Pearl’s CEO] is someone I knew I could learn a lot from — he’s driven, smart, and a great person. But beyond that, the retention here is amazing – >60% of the team have been here for 2+ years. People stay. And a lot of folks have worked together before, which says a lot. That kind of loyalty and shared history really stood out.
How do you support cross-functional alignment and strategic priorities?
We have a very intentional cadence. Mike and I set weekly goals for the company which we closely monitor to keep us focused and ensure everyone stays on track. The C-suite meets weekly, and we come together in person at least once a month. We also have monthly leadership meetings — with all department heads — where we discuss OKRs and check in on progress.
What defines Pearl’s culture today?
Transparency. That really stands out. We share our board decks after every quarterly meeting. We post leadership meeting recordings in the company-wide Slack channel. We share summary notes from our two key strategic meetings that happen each week.
We try to keep things lighthearted too — funny memes, chat threads during All Hands, getting PEARLsonal questions. We’re working on serious problems, but we don’t take ourselves too seriously.
What excites you about the work Pearl is doing?
I think it really impacts our providers, but also — perhaps more importantly — it really impacts our patients. We’re freeing up time for providers so they don’t need to spend as much time going through paperwork or scheduling appointments. That means more time spent with patients. We’re also bringing information to providers’ attention that they might not otherwise know about. For example, we use machine learning to predict which patients are likely to go to the hospital in the next month so providers can get ahead of it and try to prevent the visit. That’s the kind of thing that really makes a difference in someone’s life.
What makes you most excited about Pearl’s future?
We’re just getting started. We’re beginning to really lean into automation and AI, which has so much potential to both reduce administrative burden for providers and improve care for patients. The more time we can give providers to focus on their patients, the bigger the impact we can make.
How do you think about leadership development at Pearl?
We recently started a program called OYSTER — Own Your Success Through Empowerment and Resources. It’s all about helping employees identify what they love, what they don’t, and where they want to go. Company-wide training programs aren’t always useful because everyone’s on their own journey. We’re trying to help each person create their own bespoke plan.
What advice would you give to future leaders in this space?
Honestly — just go and do it. Healthcare is hard and complex, and making a difference in it takes guts and persistence. But there’s also an incredible community out there that wants to help. Take advantage of it. And don’t wait to be ready; just start.
Any office quirks or favorite moments that stand out?
So many! Sophie makes sure we all have lunch together in the New York office, and it’s become this really grounding moment in the day where we connect — it’s such a nice way to get to know people personally.
Also… yes, we’re a bit nerdy here. Star Wars, Lord of the Rings, you name it. There was even a lightsaber battle at one of the retreats. Everyone has their niche, and I love that.
What snack could you never run out of?
Can I pick two? One would be chocolate — I’m totally obsessed. I have to admit though, it has to be European. I know that sounds really obnoxious, but since I’m from Europe, I think I’m allowed to say that. The other one, which everyone already knows about me, is potatoes. Any form — roast, fries, baked, mashed — I’ll take them all.
If you could swap jobs with someone at Pearl for a day, who would it be?
I would like to swap with Radhey — or anyone on the Customer Success team. I just think getting to spend so much time with clients is such an incredible experience and a great way to actually get to know our business and what our customers really want.
As Pearl continues to evolve, Ciara’s role remains central to keeping the company aligned, grounded, and moving forward. Whether she’s coordinating leadership goals, refining team processes, or just sharing chocolate in the kitchen, her work is a reminder that behind every great strategy is someone making sure the pieces connect — and the people feel connected, too.
Interested in joining the Pearl team? We’re currently hiring across various departments and roles. Check out opportunities on our Careers Page.
