Why Women’s Healthcare Is Still Broken, and How Lori Casselman Is Building the Platform to Fix It

Welcome to She Built It. I'm your host,

Melanie Bar. Building in healthcare

requires more than a strong idea. It

requires operational discipline, trust,

clinical credibility, technology

compliance, and a business model that

can scale without losing the human

experience. Today's guest is building at

the intersection of all of it. Lori

Castleman is the founder and CEO of June

Health, a virtual women's health

platform designed to deliver

comprehensive expert care across every

life stage through one connected

experience. June brings together

clinical care, mental health support,

nutrition, fitness, family and caregiver

support, care navigation, prescriptions,

and supplements. But what makes the

business especially interesting is the

infrastructure behind it. A platform

model built around personalization,

access, expert care, and coordinated

support. Lori brings more than 20 years

of experience across corporate health

strategy, insurance, digital health, and

emerging health technologies. She's held

leadership roles, giving her a clear

view of how health care, employers,

benefits, technology, and consumer

expectations are changing. She built

June Health not only to improve women's

care, but to build the smarter, more

scalable model for how that care is

delivered. Thank you for joining us,

Lori. Where do you see the biggest

opportunity for AI to improve women's

health outcomes and care experiences?

One of the really key areas for us is

optimizing the practitioners and really

being able to take this incredible

expertise that clinical um

practitioners. So, women's health

experts like OB/GYN practitioners, nurse

practitioners who have done whether it's

fertility training, menopause

certification.

We want to be able to really support

those practitioners to be able to see

more patients. It's about uh driving

efficiency within their work

environment, taking all of those

administrative tasks sort of off the

table for them. So that's one key area

for us. Second key area is leveraging

the tools that are available to allow

our developers to code and build more

efficiently and more productively. We

have big vision. And there's a lot of

innovation happening within our

business. There's incredible tools at

the disposal of product designers and

developers and all really in the spirit

of driving better engagement for our

members, better utilization, better

care, and ultimately better health

outcomes. And I just keep thinking for

the practitioners, if you have all that

data and as a consumer, when you show

up, you can get to the heart of health

quicker and be much more efficient.

Absolutely. There's pattern matching for

example in some of the algorithms that

we've built into the onboarding process

for our members where we ask a series of

questions to really understand are they

struggling with some of their

demographic information etc. And then

you can really start to surface

intuitively leveraging AI. Are you also

experiencing any of these symptoms

because there's patterns that you're

able to tap into and I think it serves a

couple of really interesting purposes.

It helps the member feel like they're

not alone first of all and these that

they're experiencing as much as they

feel very personal and everyone is

unique. There's patterns here and

probably you may be experiencing some of

the following or their women at your

stage with this symptom may also feel

this type of symptom. And so do you

think there's interesting opportunities

for us to ensure that the member is

feeling heard and then to your point

leverage that data to create efficiency

in their care journey and in

understanding their and matching them to

the right practitioner at the right

time. What is your biggest growth

challenge right now as you scale June

Health and how are you thinking about

solving it?

Our biggest growth challenge is that we

want to do so much. We have a really big

vision for the company. There are many

different aspects of women's health care

and supporting women conveniently and

effectively that we want to build and

staging and sequencing what we build

when and also being somewhat patient

with stage that we're at the resources

we have at our disposal while still

moving as quickly as we possibly can

doing as much as we can and driving for

that vision of closing the gender health

equity gap. and you're solving complex

problems. So I can see how that growth

is not always easy to map moving

forward.

Yeah, it's not always easy. One of the

key things that's underlying many

challenges, especially in a business at

our stage where we're 3 years in, the

talent that you have sort of on your

team and around you is is critically

important. You have to surround yourself

with really smart, really motivated,

driven people who are also passionate

about the problems that you're solving,

who have complimentary skill sets. And

the reality is sometimes this talent or

team members that are appropriate at a

certain stage are not always the same

talented team members that are

appropriate at your next stage. There's

also an element in growing and thinking

about those growth challenges and those

growth ambitions. It just comes down to

okay, who's doing the work and have you

surrounded yourself with the right

people to lock arms and dig in and do

that work together and that iterates. It

evolves over time. And how are you

protecting and building a strong company

culture inside a virtual health

platform?

Most leaders need to pause on this one.

Culture is everything. I'm a huge

believer in if you create a great

environment that people want to be part

of and allow them to thrive, magic

happens. We have a lot of norms and

processes within our culture that we

stay very true to things like a regular

cadence of bringing the team together.

It's one hour once a week, but even if

you're pulling from people to bring that

agenda together and perhaps one week

you're feeling like the agenda isn't as

deep as it is another week, you have to

be really committed to just that

connection, especially when you're a

virtual team, which we are. We have

employees all over the country. In many

cases, people that have been on our team

for a number of years now have never met

anyone else in person. those norms and

connection points are really important.

And then the other thing is surrounding

yourself with really talented people and

then getting out of their way. For

myself as a leader, I think about this a

lot, especially given I'm a founder and

obviously I care very deeply about the

business and many aspects of the

business. This is the hardest following

this rule has ever been cuz you want to

have eyes on and touching everything.

But at the same time, you have to flex

that trust muscle. It has to be part of

your culture. And you have to find great

people and let them do what they're

great at and what you hired them in the

first place to do. And you can't be

great at everything. Know your strengths

and lean into those strengths and let

other people do the same thing.

Celebrate the wins. We don't do that

enough because everything feels hard.

That's a key culture thing, too, is take

a moment, whether it's in those weekly

meetings or messaging to the team. Even

if the wins are small, you need to

celebrate them.

And it's interesting cuz I think I used

to be better at celebrating the wins,

but now as things are moving so quickly,

thank you for bringing that up because

it gets lost even more so today. It's

funny, a little personal story here. I

saw my brother on the weekend and he was

saying, "Wow, you've done so much in the

last couple years and you've just hit

some key milestones. Are you feeling

proud of yourself?" I had to pause for a

minute because to a large extent, no, I

haven't been taking a beat to feel that

pride because I'm constantly thinking

about the next thing that we need to do.

But it's such an important reminder.

Celebrate the journey. And thank you for

bringing that up. We used to talk about

it a lot on this podcast and you

bringing it up made me stop and think

we're moving so fast that we're not

really doing that so much anymore. And

you're right as a founder one of the

hardest parts is saying am I the

bottleneck? Am I stopping the growth

right from moving forward

right? It's a hard mirror put up against

yourself. But it's also great to check

in with your team, especially some of

the folks that have been with you for a

long time or some of the leaders that

you spend sort of the most time with on

a day-to-day basis and get that

feedback. I mean, the difficult

feedback. Am I getting in the way? Am I

slowing things down?

What is one honest lesson about leading

people in healthcare in a startup

environment that you wish more founders

talked about? It goes back to that point

I just talked about with sometimes the

people that you surrounded yourself with

to get you to a certain point are not

necessarily the same people that you

need to achieve the next set of

milestones or objectives. The hard part

there is a lot of loyalty and trust that

goes into building something together.

It can be really hard just that point

where it's not working. Too many

founders let that drag for reasons that

I touched on, right? loyalty, there's

experience, there's having been in the

trenches together, and it's tough to

call that out. But bottom line is when

you you know it in your gut and in your

heart, you just need to deal with it

because everyone around you, right,

whether that's your investors, your

adviserss, even your clients, everyone

around you feels it when you are not

dealing with it. as hard as it is, is

one of those things where you just have

to push yourself to the band-aid off and

deal with the problem once in your heart

that change needs to happen.

Yeah. And trusting your instincts.

Exactly. Exactly. What lights you up the

most about what you do and makes you

excited to continue building June Health

every day?

I feel like we're doing something really

important. We hear it from our

practitioners and our members. I've been

fortunate that throughout my entire

career, I've worked in healthcare and

insurance my whole career. I've worked

in a space where I feel like work that

you're doing, as much as it may seem

somewhat removed on a day-to-day basis.

Heart of the why is improving people's

lives, that is the heart of our why at

June Health. And we believe and we see

it every day that we are impacting

women's lives. and big ambitious goal is

to make a dent in closing that gender

health equity gap. That lights me up and

I see that we're hitting milestones and

adding incredible new people to our team

and we're expanding these care journeys,

meaning we can touch more lives and

solve more health challenges for women.

That's very fulfilling. Those are the

things I think about on the long walks

at the end of a very stressful day. It's

that member testimonial or that story

you heard from a practitioner where even

if there were a few tough ones in any

particular day and challenges that

you're needing to solve. You have to

anchor to some of those positives to

know that you are making a difference

and that definitely lights me up. I feel

passionate about the work that we do.

And it's great that not only can you

love building the business but have the

passion and the mission behind it.

Exactly. I work with an incredible team.

That lights me up too when you see

someone else getting as excited about

your vision for the business that you'd

been thinking about for many many years

and they're now on that journey with you

building and they're as excited about

that vision now as you were many years

ago. That's super fulfilling and

exciting too. I love those moments where

we have a conversation sometimes even

with our investors or advisors where our

clients and our clients are often

companies. We sell June as an employee

benefit as well into companies. And when

you get on those calls and they're just

as excited about what you're building

and the impact it could have as you are,

that's super fulfilling. So true. And

I've loved building a global team and I

love it when my team challenges me and

says, "Hey, have you thought about

this?" and surrounding yourself with

innovative people has been so much fun.

Yeah, absolutely. I couldn't agree more.

It's tell me something I don't know. How

would you think about this? And ideally,

it's very differently than how you think

about it. And then that combination of

different perspectives just elevates the

solution that you're building. And it

took a while for me to think, I want

this. I want someone to challenge me. I

want someone to come to me with

innovative ideas. Yes. All the time.

Especially how fast we're moving. Yeah,

absolutely. One of my principles of

leadership is if I don't know, I can't

fix it. I really do ultimately encourage

people around me and the people that I'm

working with to find a moment or a

constructive way or a channel to share

feedback about what's happening in the

organization on their team with me so

that we're eyes wide open and it just be

data point that we can work to solve

for. So true. I have a potential client

that I might be working with and I keep

sharing information with her whether she

becomes a client or not. I want her to

know the information because I as a

leader would want to know that

information.

Yeah. Sometimes those can be tough

conversations whether you're on the

delivering end or receiving end. But

ultimately it's all in the spirit of

evolving and improving. What is one way

that you protect and cultivate your joy

with your work and your life today?

Ultimately, I'm probably not doing it as

well as I would like to in this early

0ero to one stage. But for me, it's all

about family and relationships, spending

time with my kids and my husband,

getting outside. I try and protect at

least 45 minutes to an hour a day to

hike or be outside, even if it's just

walking the dog and taking him on a

little extra walk. My dad taught me

really early on in my life when you're

going through a stressful time, go back

to the basics, which is chop wood, carry

water philosophy. Sometimes you just

need to get out and garden or do some

sort of hard work and turn your brain

off a little bit and turn on the

physical side. That definitely can bring

me joy as well. And the last thing is

traveling. We travel as a family quite a

bit and I definitely love seeing new

places and expanding our horizons.

It's amazing the perspective that you

have when you get outside and then

having a dog is great because it forces

you to get out and take those moments

even when you might not decide to do it.

It's a calming thing to just spend time

with an animal and like slow down and

walk a dog and sometimes you need that

at the end of a very busy day.

Yeah. Thank you so much for everything

you're doing to improve women's health.

Can you please share with us how and

where we can find you?

We are June Health. You can find us on

Instagram, LinkedIn. Our website is

www.junehealth.care.

Connect with us on LinkedIn. be really

happy to hear from anyone.