Christine Evans, Chief Marketing and Strategy Officer of Headspace Health, shares her career journey on this episode of the Leadership Backstory.

Christine retraces her journey from the fashion world to executive marketing roles at leading health-related brands like Fitbit and Headspace Health.

There are lots of leadership lessons packed into this episode.

We learned a lot, and we know you will too!

Visit Headspace Health to learn how they’re transforming mental healthcare: https://www.headspacehealth.com/

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That shift from building hard skills

to soft skills and soft skills really being the unlocker,

if you desire, not everyone does, to be at a certain level within their career.

It is instrumental to where you want to go because

it means that you can get work done with other people.

It means you can build relationships.

It means that you can have context in everything that you're doing.

But in that shift, I would say it's a really hard one.

I found that myself, even in the second part of my career.

And certainly I see that with a lot of, especially, I would say, women.

That's Christine Evans, chief marketing and strategy officer of Headspace Health.

Christine chases her journey from the

fashion world to executive marketing roles at leading health related

brands like Fitbit and Headspace Health on this episode of the Leadership Backstory.

There are lots of leadership lessons packed into this episode.

I'm Peter Barron and my co host, Brendan

Steiner, and I learned a lot, and we know you will too.

So let's get started. Hey, everyone.

I'm Peter Barron.

And I'm Brendan Shiner.

And welcome to the Leadership Backstory.

Brendan, this is going to be a fun interview.

We have Christine Evans on the call today.

Christine, welcome to the podcast. Great.

Thanks for having me. Yeah.

So Christine's got an amazing career.

Brendan, you have a long relationship with her.

So I know you'll talk about how you guys

met and all the things that happened there.

But Christine, you are now the CMO and

chief strategy officer at Headspace, which fascinating company.

I remember listening to a podcast with

your founder a couple of years ago and being like, Wow, this is super cool.

You're doing all sorts of neat things there, but we're going to get there.

But there was a whole journey that you took to get to that place.

I've joke d on the pod before that LinkedIn is my source of truth here.

I've got it up in front of me again.

Fascinatingly enough, you started in the fashion industry.

Is that right?

That's right.

My college degree is in textiles and apparel.

I had a very different college experience in which I learned

how to silk paint, how to embellish, how to drape, pattern

making, while getting a great liberal arts education.

I graduated and was like, Oh, I guess this is what's happening.

This is what I'm doing.

I worked for six to seven years or so in New York as a

sweater designer for a number of the bigger box brands that you

might know of. Ann Taylor Loft, which is a brand part of the company,

what's now called Macy's Merchandising, so private label for them.

And it was just a fascinating experience.

My first time living in a big city.

I lived in New York City for about six to seven years, again doing that.

And it's a part of my career

and of my life that I think was just so instrumental in helping me to figure out.

Certainly, who I am, but really what I

want to do, and what gets me up in the morning.

And if I were to put any headline on that, and it's so interesting

in the time of the pandemic right now where people are really

reevaluating what they do with their time and how they spend their lives.

I would say with that experience, you also don't always have to do what you love.

And sometimes the things that you love need to stay the things that you love.

And preserving the sanctity of that can be really important.

So that's a big headline coming out. Of that.

Yeah. No, I'd love to hear more.

Me too. I've always had an interest in

fashion and design and throughout my life really have been

both interested in the arts, both musical, visual, et cetera.

And I like making stuff.

I wouldn't call myself a crafter, but I'm really into the textile arts still today.

And when you get into the industry of it

and you see what happens, which is a really instructive process to go through.

For example, and I don't know how it is today because it's been many years since

I've been in the industry and I'm sure it moves much more quickly.

But at the time, you're really going

through the process of developing a set of products and a set of offerings

12 times a year on a very regular basis in a way that's time boxed in a way that is

process oriented and repetitive and great if you're an early career

because you know what it takes from a collaborative standpoint to know

everything that goes into this thing that I'm wearing today.

And so that part of it I think was incredibly helpful for me.

I think as I got through that part of my career, a couple of things.

Became obvious to me.

One, as I looked at the folks who were in leadership positions

with these companies, where you step away from the data design

role, where you're not actually sitting there sketching something.

The thought of that was just not that appealing to me.

I love designing.

And I'm sure that if you talk to folks who have been in the design world, I think

that career progression can be a really tricky

one because you generally go into it because you love doing that thing.

And I didn't see myself becoming a creative director.

I didn't see myself becoming a VP of design.

It was not that interesting to me.

And so probably about the fifth year through my career...

So I'll give you a lens into what it's like to create a product.

We would design its design as about three times the amount

of product that would come out into the store.

And when we narrow it down to what we want

to produce, we go through a whole process of working with our vendors

overseas, working with fit models that are specifically

designed with dimensions to be able to represent your buying customer.

And I remember there was, and it's so present in my mind.

So I was a sweater designer.

I designed a lot of twin sets for women who are working.

And this particular twin set was a July delivery piece, and it was white.

It was made of a synthetic knit material.

And I'm going to try my best to describe this.

It was like cutting at the shoulders.

And then if you see this neckline that I

have here, it was crochet all the way around.

And then there was a cardigan that went on top of that match.

And I remember I

spent, along with many of my colleagues, we'd sit three hours

weekly in these fittings where the fit model tries things on, and

we'd have a discussion about how someone would use this product or wear this.

And this was a very controversial twin set because

we have a target person who's going to where you expect would wear this to work.

And the question was, what happens to get her bra strap shows?

It was like, well, it's see through here.

It's like cut in here.

And everyone's like, Well, she's going to wear the card again.

So it doesn't matter.

They'd be like, No, she'd wear a strapless ball.

And then people would say, well, no, no one wears a strapless bra.

And I ended up over a two week period with this

particular skew talking about this hypothetical woman's bra strap for hours.

And I remember

being in my apartment sitting back and I'd be like, This is an important problem.

But this is not the problem that I

actually want to be solving is a bra strap.

Hypothetical issue.

What's so ironic about this and funny is

at the time I was living in New York, and you do that thing where you spend $700

to build some dry walls so someone can live in the dining room.

That was her living situation.

I was in my room, my doors closed.

One of my roommates who was worked

for judge out in New Jersey during her clerkship, she knocks on my door.

She's like, Hey, Christine, I have a question.

I need your advice on something.

I open the door and she goes, Do you think it matters that my bra strap's showing?

S he's wearing the thing.

T his is a year later because it had taken time to hit that.

I just looked at her and I was like, You

have no idea how long I've talked about this.

Did she know you designed that one? No, I don't.

Think she did. I mean, she knew it was from...

But she didn't know.

That started my journey of like, I know I don't want to be doing this, but

I don't know what I want to do. And so I did all sorts of...

I studied for, I don't remember, my GRE.

I thought I might want to be an architect.

And I was like, Well, that probably

presents the same set of issues that I'm probably having today.

And I ended up taking my GMAT and

I went to business school with no idea what I wanted.

To do.

No real business training.

And so you're in an environment where

you have a bunch of people who have been investment bankers and management

consultants and navigate their way around Excel spreadsheet with just the keyboard.

And my experience with Excel had been

like making perfectly square boxes, like making a list.

That was it.

And so that was a real eye opener for me in terms of the skills that I

probably needed to build to likely make some type of change.

I thought maybe I'd get back into the

merchandising side of the apparel industry.

And what ended up happening is I ended up

falling really in love with health care marketing, which sounds

bananas because it is literally the complete opposite in so many ways.

One of the first roles that I took... So a couple of things.

I graduated from from business school in

2009, which was the first year out of the Great Recession.

So here I am, a former fashion designer with debt and no real skills

trying to find a job that I could work in. couldn't really describe.

So some hustle in there.

I took a bunch of either unpaid

internships along the way and fell into health care marketing from there.

And I don't want to say the rest is history.

That was a journey from there.

But that was a pretty critical point for me in terms of finding meaning in my work.

Solving the problem that I love solving.

And interestingly enough, I think applying a lot of what I learned in the previous

part of my career, which again, I believe to be really instrumental to my

personal and professional growth into where I am today.

What drew you to health care?

So a couple of things.

A lot of my family are in health care.

My brother's a surgeon.

Brendan, you remember Jason, my brother?

I do. my brother's a surgeon here at UW, and my father was a surgeon.

So a lot of medical folk in the family, and I

always found it really fascinating, just the practice of it and the meaning of it.

As I described in the apparel industry,

when you develop a product, it's probably months now, but at the time, it was like a

year to bring a collection out to market and contrast that with...

My first few roles were in medical devices where you have one.

Product.

It takes you 7 to 10 years to bring this thing to market, and the regulatory

environment in which you get to operate is like this big as a marketer.

And that to me, like, weirdly, I found just like the most amazing challenge.

What can you do with this tiny box

with this time frame that you have, again, 7 to 10 years, maybe if you're lucky, 5.

And I just found the challenge of that totally invigorating.

And to be able to see and to talk to folks.

Very similar to I used to live on the

subway when I lived in New York, to be able to see people wearing something that

I know I had a hand in. and then just wondering what got them to do it.

And in my early health check career, I spent a lot of time

with patients themselves to understand what

is it they would want from a product, what would get them to use

an early company I worked for, worked on a wearable ventilation system for people

with COPD, which is a progressive disease, it's not curable.

These are people in stage three or four.

Of a really debilitating condition.

And being able to say, what would get you to use this outside

of your house and walk around in a way where you wouldn't feel ashamed, where you

would feel comfortable, where it would be easy for you to use?

And that type of usability, which is practical but also really emotional

in the same way that picking something out for my stores and

deciding to pull that out of your closet every day is.

There was a real connectivity there for me.

On that.

There's a real depth of looking at their LinkedIn profiles.

That was when you were at breathe and you were doing product marketing.

Product marketing, does that just not give you the opportunity to expand what

marketing is traditionally considered to be?

You're in at every single phase of development from sizing the market to

doing the work that you were just talking about, talking with folks.

How did that layer on early on in your career?

I'm super curious.

Product marketing in this part two of my career has been foundational and

really the real bias towards it, and primarily

because you're sitting at the intersection, as you

put it, of both creation and communication, which is how do we

influence and bring an organization along to really represent what clients

need, and then how do we communicate that back out to make sure that people

know that this thing is available and that they want to buy it.

And I accidentally

fell into this like, I found it was primarily because in business...

So in business school,

business schools today, I think, have you working in small groups all the time.

And my role in business school was to make the PowerPoint always.

That was my one skill.

And so that translated actually pretty well into the workplace because as I got

into product marketing roles, a lot of what you do is actually communication

through slides and being able to tell that story in that way.

And so that was, I'm going to say, it was a total fluke because it was.

But that happened purely, I would say, by happenstance in a

lucky accident of just having played that role both

academically and then transferring that practice skill into my day to day life.

And really being in the early days, both at Reeve but especially at a company

called Cast Light Health, which is still based in the Bay Area.

When I joined that company, it's about 60 people.

And one of my jobs to be done was to create and work in partnership with our

sales team to make sure that they could express what it is that we had, which was

this ability for employees to go and shop for health care in a price oriented way,

which sadly blows people's mind then and still does today.

But nevertheless, getting into that practice of connecting a buyer and a

consumer need and that communication of that format.

It was a lot of that early product marketing work.

And over time, you build enough expertise in both your product and your customer.

Really, the business of what it means to

bring this product to market, it was quite translatable, I think, into

further parts of my career, certainly a bit now at Headspace.

Product makreting, I think, is the in particular within health tech and

technology companies is the basis of connecting great ideas to business value.

Well, Brendan, I know you've got a

question, but I just have to say, you know you're talking to a skilled

product marketer, somebody with a deep foundation when they use jobs to be done.

I'm like, there you go.

That is brilliant. I love it.

Yeah.

Here's the question, Christine, before we go further.

People know you're a former student of mine.

Now, it should be known that

I don't think I ever taught you because you were too smart.

You were not in my classes, which is this is a bonus for her.

This definitely speaks highly of you, Christine.

But going back to high school before

college, were some of these things percolating in

your mind, or what were you thinking back then?

Did you have any idea?

Gosh, that's so...

I mean, in theory, I was like, Great,

it'd be great to be a part of a brand.

But I had no concept of what it meant to really work in this type of environment.

And again, from a family standpoint, I was surrounded.

My dad was a surgeon and a physician.

And so we had a family business.

So that's really all I know.

And I just had no real

practical or even really adjacent to experience of what any of this

means, which we can talk about maybe some of the impacts down the line of that.

But I think more than anything, I really had no idea what I wanted to do.

And I went into college, just very frankly, I applied, I remember, early

decision to college with the hope that they would just accept

me and that show of I will take this role if you take me

would be enough for them to say, Yes, we'll take you.

So that was vastly simplified.

And also, I don't want to say I cut myself short, but I just didn't know.

I knew that I loved textiles

and art and doing this thing, and that I just fell into it.

And I say that from a place of enormous

privilege to be able to say, Well, if it doesn't work out, it doesn't work out.

All those things.

You have to recognize that that's a key part of this.

But I had no idea. I had no idea.

It's just no idea.

Yeah, that's totally fair.

Clearly, we'll talk more about

it, I've had a ton of success and we haven't talked to each other for

years and I get a real sense of confidence.

Did you have that back in school?

Because I remember you being a very good

student, more quiet, and you followed rules.

Is that fair? As far as you know, I followed the rules.

Please don't. I was the Dean for a few years.

The less I know, the better.

Although I think the statute of limitations has passed.

But have you always felt confident? And no?

Yeah, you're. Shaking your head.

Oh, my gosh, no.

It really has been only with it, I would

say, specifically the last 10 years that you re.

By nature, I am relatively introverted,

and I get very nervous public speaking. I don't love it.

I am just not someone who loves to be on stage.

I'll put it that way.

But I learned a lot, I would say.

So a couple of things, I think you're absolutely right.

And I would say through college and certainly through my early years of work

before I went to business school, very, very quiet.

Not someone who would advocate for myself, not someone who would raise your hand with

a new perspective or new idea, just not that person.

And business school was a real wake up call because we would have these...

So what they do is they have a lot of the

big consulting firms or big CPG companies as students are starting to graduate or

look for internships, they bring them on campus and they do these networking

sessions, which was the most terrifying thing in the world.

I hated it.

I didn't wear suit.

I mean, just the whole thing just sucked big time.

I

had the opportunity, but I'd never really been forced

into building that skill of making connections with people that you

know in a way where it might have a business outcome or that

your job might be at stake or whatever it might be.

And so that

was very difficult for me, especially as I mentioned, it was around the 2007 to 2009

time period when the job market was really not great.

And so not only do you have someone who's

like, no marketable skills, but also doesn't talk.

And that becomes tough.

And I think what I learned over time, certainly observing a lot of my fellow

classmates at Kellogg who had been in these environments,

whether they'd been like agency ad agency folks, whether they'd been

investment working is they really learned how to ask questions.

And when you get down to it, I think a lot of my quietness comes from

a lack of conviction of the thing that I'm going to say being right.

Is that this thing I'm going to say, Be right and I'm going to say be right?

Am I going to look stupid? And I think the reality is the best people

that I observe would always ask a clarifying

question, would never apologize for asking that question, and used

whatever the output was of listening to whatever the response

was to inform was a really well rounded

either response or output or project or whatever it might be.

And I guess I learned a lot from there were very specific folks

I remember through my business school career, which is like fabulous at this.

Something that we might want to talk about coming is failures.

But I do think that a lot of when I think about

small failures, medium failures, and bigger failures are just this

anxiety around not being right or doing something wrong.

And sometimes you're just never going to know until you make a mistake either.

And you have to be okay.

With well, that's where all the good stuff comes.

You get that feedback, you're like, oh, okay.

Maybe I go this direction instead of that direction.

The other thing I love is...

When you're okay with knowing that being publicly wrong can sometimes be okay.

It's really freeing.

But isn't that also cultural, too?

Depending on the company that you're at, if the leadership is setting the bar that,

hey, it's okay to make mistakes, this is how we're going to learn and grow.

Was that part of the early companies that you were with?

How did you gravitate towards that after you left business school?

Yeah, it's such a good question.

There's two cultural components for me personally.

One, which is my upbringing.

I'm Chinese by background. I was born here in the States.

My parents are both from Taiwan.

I grew up in a very conservative upbringing of education

as the most important thing that you can do, and your test scores matter.

It's very binary.

And this comes from those of us who know folks who have integrated even recently.

The pressures are very different in that culture and in society.

Particularly in the East Asian countries.

And that translated into my upbringing but doesn't actually translate into work.

Meaning

what I found oftentimes, and I remember early on my career, a lot of my

frustrations were like, I know I'm the best at this.

I know I'm so good at this, but why can I

not either get ahead or why am I not getting promoted?

Why? Why?

Why? Why?

Why? Why?

Why?

Without ever saying anything about it or asking the question or getting feedback.

And I remember when I quit my job at Ann Taylor,

I'd been there for about two years and it was a wonderful experience on the whole.

But I'd become really frustrated because I hadn't been promoted and I was

watching people around me getting promoted.

So I quit, found another role.

And on my exit interview, I chatted with her name is Sherry Hershawne.

I have to forward this to her after this because it's always stuck with me.

But she was our executive director of design and she called me and

she goes, So are you quitting for more money?

Is it because of promotion?

I'm like, Yes, honestly, it's all of those things.

And she just looked at me and she was like, Well, did you ever ask for them?

I said, Well, no.

She goes, all right, well, if you don't ask, I'm definitely not going to get it.

And I remember walking into that conversation like, oh, that was so mean.

But it really stuck with me.

And to this day, I don't know if I've

actually told her the story since because we've been in touch periodically.

And the years past, but that always stuck with me.

It's just never...

If you don't ask, right?

And even if you don't feel that confident

in asking, or what are the questions you can ask leading up to that question?

I've never done the discovery around me to do that.

So of course, you're going to feel a little anxious about asking for promotion

if you're not taking those steps to get there.

One

of the things that I certainly saw with myself and I see even, especially with

women on my team or those that I mentor is that shift from building hard skills

to soft skills and soft skills really being the unlocker,

if you desire, not everyone does, to be at a certain level within their career.

It is instrumental to where you want to go because

it means that you can get work done with other people.

It means you can build relationships.

It means that you can have context in everything that you're doing.

But in that shift, I would say, is a really hard one.

I found that myself, even in the second part of my career, and certainly I see

that with a lot of, especially, I would say, women today.

How did you cultivate that for yourself personally?

Practice? Honestly, it really comes down to just

trying things over and over in smaller settings and in bigger settings.

I've been lucky.

So, so fortunate, certainly within the last 10 years of my career, to have people

who believed in me probably more than I did

myself and really pushed me to be out in front,

really gave me, maybe sometimes unsolicited feedback

in a way that I thought was actually quite healthy for me.

And so from that standpoint, I would say I had a lot of people.

Supporting me and rooting for me along the way in ways that I maybe didn't even need.

That's something that I reflect on quite a

bit in my role now and in the years out of that context that I can help provide from

just experience of having people had that done for me.

Then taking those opportunities and not

shying away from them is that second step that I had to take,

and I think all of us have to take when people make that investment in you.

I love it. Talk about Fitbit.

So you, in 2014, moved over to Fitbit.

Was that right around when Fitbit came to market or had it been around earlier?

I can't remember. It had been around.

It was just becoming the thing that everybody was getting for Christmas.

And for me, it was a really, what I felt was a pivotable time for me

personally in my career because I was getting back to what I felt was

an exciting consumer brand, but within the context of the things that I had started

to build a career and not what was good at.

And at the time, I had been brought in

to help grow the B2B side of their business from a marketing perspective.

So they had a thriving consumer business.

And what they had found, not so different from headspace, is that companies were

calling them up and saying, Hey, I want to buy a thousand of these for my employees.

What can we do?

And so taking the signal, I think they made a

great investment in bringing in teams and people and leaders, including me,

to be able to help build what today under the Google umbrella

is Fitbit Health Solutions, of which some dear friends of mine still do that.

So that was instrumental in being able to, I think, tie those two pieces together.

Something that can, of my background, something that

can feel hicky to marketers, which is health

care. Health care, yes, health care is very messy.

It's also

important, instrumental what we do, and how we live and thrive as a society.

And then there's a consumer brand that people love.

And I was fortunate enough to be able to

work at a company that was stellar at that, right?

And be able to help

propel at least that side of the business through, I think, were some really

incredible tailwinds that had been built there.

And it's an experience certainly that I've taken with me in my role.

At Headspace today.

I mean, what a transformational product that was.

For me personally, it was the thing that...

First off, I had never been obsessed with steps.

Then I became obsessed with steps. Okay.

And then I got in a little circle and I started competing with people.

I'm like, Oh, I'm going to beat that person today.

There's no way they're going to beat me.

But what it ultimately unlocked for me is

the concept of I'm more productive when I'm moving.

I think clearer when I'm talking to people.

That was just transformational stuff.

And if I looked at it personally, would I draw a line to that, to health care?

Probably not in the moment, but now, absolutely.

What a cool opportunity.

Was that the first chance that you had to manage large teams?

Or were you managing before then?

That was my first opportunity to manage a

larger, I would say, multi disciplinary team.

So I came in in a marketing generalist role.

So they were like, We need a marketer doing these things.

And I said, I think I can do that.

And so I came in and part of my experience, certainly

at Cass Light, which at the time that I was there...

So just to describe this really quickly so

you could understand the transformation of these companies in both cases with Cass

Light and with Fitbit, I had been with them

half of my time as a private company and half of it as a public company.

And so that transformation that you go

through in terms of product, in terms of process, in terms of

culture, all of those things is a pretty monumental thing to witness.

So I left Cass Light, having just been a part of that transformation as a company.

And I think with Fitbit.

I was prepared and ready to take those learnings and

certainly be able to quickly identify, if you have job interview questions, when you

come in your first 90 things, what are the first three things you're going to get?

I knew what the first three things that I wanted to get done were.

I was probably right.

I thought I was right.

And a lot of it was product marketing that's a bias.

The second was to find and finagle our way to at least

experiment with getting a little bit more of.

A scalable demand generation ad gen.

And then the third, interesting, probably the least important of those three at the

time, was to build a brand that could be relevant within the healthcare space to

what is a pretty conservative buying audience, i.

E. A health plan or health system.

Because in that case, as we found, and I

still find today, an amazing consumer brand can be a little bit of a

double edged sword within those circumstances.

So it really came down to in my lived

experience of having observed the set, cast, light, done some of it myself, what

are the first three things that I would do?

And I had, again, just an incredible set of people around me and above me who

believed in that and who helped me invest in that.

And it's just an incredible experience.

How did managing a large team feel at first?

I'm so curious how that works for folks.

Every time we do have one

of these interviews, we talk about the first time that they manage large teams.

And it's just interesting to see how people remember that time.

It's almost so jarring that you don't

realize how jarring it is until after you're done doing it.

Honestly, it was day one.

It was just me.

And in nine months, it was 20 people.

You almost don't have time to think too hard about it.

You just have to respond.

Which in many cases can be the downfall of a team if you're not very deliberate

also about how you build and invest and pace against the business as well.

And we're seeing a lot of this today, certainly within the tech environment.

Of growth at all costs.

And a lot of that comes down to your investment and talent and people.

And while I don't think that

I had ever necessarily thought about it in that way, you were always trying to get

ahead of what you thought would be happening versus...

And that's what I wouldn't say a failure, but a learning from my perspective

is like, Well, if I hired this person, then I can get this thing done.

So we'll justify this team or this budget, and then we'll do it versus saying, What

are the three small ways that I can show that this actually scales?

So that I will build a team, so that I will have the program budget, so that I

will go create this enormous go to market strategy and slow the roll on that.

So with that, I would say

certainly I learned a lot about better ways to scale teams.

Because ultimately, when people feel that

they can be successful in a role, when they're really clear about what they're

going after, when they're excited about what they're going after, and

the end in mind is very clear for them, you can build a great team.

But if you're operating in an environment where you're like, Oh, let's try this.

Let's do this.

And we think we're going to do this thing, but we're not sure.

It's really jarring.

I am someone whose eyes are always bigger than my stomach.

Anything that I've learned, certainly in that role, is slow the roll a little bit.

That's my bias.

As I think about building teams and certainly my next level leadership

always looking for folks who can check me on that.

Is this someone who

is more cautious, more skeptical, maybe, than I can be, and who would be unafraid

to tell me that they either think I'm wrong or could be.

Doing it differently? I completely agree.

Getting checked is a gift.

But having folks feel like they can check can sometimes be challenging.

How do you nurture that?

It's such a good question.

I think you have to model the behavior first and foremost.

Oftentimes, well, I'll do is actually

call out in a positive way, someone, Hey, so and so brought this to my attention.

I need to think about it.

I'm so glad they did.

Thank you.

And doing that publicly, especially now, and folks

everywhere right now are really struggling with balancing work life, we're all

sitting at home and have no real social interaction with people.

And it's a generally tough time right now.

And so people can...

We are not able to build relationships

in that same way that create a sense of psychological safety as automatically

as we would if we would be in an in person environment.

So you have to expressly and explicitly build those relationships as well as

call out and really reward people for questioning bias, for

challenging the status quo, and recognizing that, and we may not always

take the suggestion, but let's recognize the merits of why this came up, why

it may not happen, or why we may save it for the future.

I think when people see that over and over again.

It's quite helpful.

Go ahead, Brandon. Sorry, Christine.

So when you had mentioned

back when you were designing and as you would potentially

move up the ladder, so to speak, you would get away from designing.

Have you found that the same in marketing as you've gone up the ladder?

Have you let go of stuff or had to let go of stuff that you miss?

Such a good question.

I have, but I think for sure.

I think it's different because

I really loved the aspect of being a creator and design

and product marketing, for what it's worth is not the same.

I actually find that the problem

or the things that I get to roll up my sleeves and dig into are just

sometimes bigger problems, or they're just problems at a different scale.

And so I don't while I miss things here and there, I generally

feel that it's just a different version of the same thing at a different level.

So that's where I found peace with that for sure.

You

transitioned in 2018 to Ginger and really curious to hear about that experience.

But when you think back on that Fitbit experience, what were

some of the leadership lessons that you took from that time?

Yeah. I get a lot of those...

One that I can describe is really just this need to be

deliberate and thoughtful about how we grow teams, grow people, grow business.

And certainly, I think there are some things that I probably would have

experimented with or done differently that had an impact on both the business and the

people in a way that I think I could have been more deliberate

about events that we threw, investments that we made.

All that stuff.

A lot of it, I feel like my learning,

again, it just comes from observing other people.

My

last manager that I had at Fitbit, who is a woman named Amy McDonnell,

and she now leads Health Solutions under the Google umbrella.

She's an incredible leader.

And at the time, this was pre... Oh, my God.

I can't think of the hashtag, but the whole Harvey Weinstein.

Me too. Thank you.

This is pre Me Too.

But there's this bubbling element of like, can women be...

Sheryl Sandberg's book had just come up.

It's like, can you be successful without being an asshole at work?

And one of the things that I have learned and continue to learn from

Amy through our observation as we had a nickname for her, which is the Delvember.

Because she was

so pleasant, she's so nice, she's so great, she's so thoughtful.

And then she knows how to get it done.

She's built the relationships to do this.

She's trusted by the organization around her.

And to me, it's like, you can be kind, you can be thoughtful,

but you can also be really clear about what needs to happen.

And I think she was just a master at doing that and someone that I learn

from and have continued to learn from, time and time again.

So that's one.

The third lesson has come to more in a macro view, and I would say is still a set

of lessons that I'm continuing to learn today is how to function in a multi sided

market, which is you have certainly within our health care system, a

lot of people who consume a service or a product but don't actually pay for it.

And so you have differential incentives, a lot of people to make happy.

And so I think it was

a really interesting experience in terms of how to balance, I think, the tensions

of what is a B2B2D business in health care, which is quite complex.

So a lot of my lessons come out of how you structure teams, how

you organize them in such a way where you can really capitalize the most on

what is an amazing brand in the case of Fitbit, but also

the technological prowess and expertise of having all this data at hand and what you

could do with that to empower people, consumers, and businesses.

And take. That with me, too.

I hadn't even thought about the amount of data.

Oh, my gosh.

It must have been a man. Yeah. So you've got these lessons that you've learned.

Now, this was the first time you've been a CMO,

so you're moving over to the CMO role at Ginger.

Talk about that because it's been a...

The whole journey all the way to Headspace.

I'm super curious about all of it.

I'd been at Fitbit for some time.

We'd been public for about two years.

One of the last things that I did before I left was I worked on the acquisition

that they did of a small company called Twine, which was based in Boston.

And as with public companies, when you do a merger, you have a really small team

that can be working on it, and you generally have to move fast, and there are

very few people who are what we call under the tent.

And I remember going through that it was probably like a

month long process of how we would communicate or how we

would get this together with the small team.

And I remember feeling more invigorated than I had in years.

I was like, oh, my gosh, I love this.

We can move so fast.

There's not a ton of process that you can or have to go through because

it's just seven people who are working on this.

And it really solidified for me as I looked for that next role.

The challenge I was looking for next was to go back to an earlier stage company.

Again, CathLite was about 60 people when I joined.

Fitbit was around 200 when I joined.

I think CathLite, when I left was about 500.

Fitbit was 1,500.

And so I started interviewing for roles.

I'm coming up on five years having been in this version of a role.

And I remember I talked to this small

company called at the time, it was called Ginger.

Io. So Ginger.

Io.

And I'd gotten outreach from their, at the time, CEO and some other

folks to come and talk to us about this role.

I was like, I know what this company does. I went to the website.

I was like, I still don't know what they do.

But I continued.

In every conversation that I had, I learned a little bit something more.

And so I went

from, Yeah, interesting, great investors, really smart people here.

I still don't know what they do to over

the course of literally six months taking on progressive conversations.

In every conversation I'd learn something new.

I'd be like, Oh, my God.

Why does nobody know this? And I got to the end of it.

I was like, Oh, my gosh. You know what they need?

They need a marketer, which is why we were talking.

And I can actually do that.

As a marketer, one

of the greatest gifts you can be given is a product that people love and that works.

And in this case, they seem to have this

in spades in a way that just no one was yet communicating.

And so I took a leap of faith and took the role.

The company had actually been around for about seven years already and had gone

through multiple pivot and to find the right product market fit.

And this was the beginning of the journey that certainly we've been on now.

And at the time, we were doing less than a million in ARR.

So it's really early.

We had a couple of big clients

and we were really building the plane and flying it at the same time for sure.

My paycheck was written by hand.

It was a big change.

It was a big change.

But

it speaks to really just the passion of people and what you can get done when you

have a very mighty small group of folks who care deeply about what you're doing.

And at the time, the first product was this text based coaching product.

We had five coaches at the time.

We didn't offer therapy or psychiatry

because that's a whole regulatory process that you have to go through.

And at the time, talk space was just becoming a thing.

But people weren't doing telehealth.

You were being like, okay, I'm going to get on a Zoom and talk to my doctor.

You were like, that's so weird.

What would anybody be able to do to me? They only knew.

For me on the. Camera, if they only knew.

Yeah, exactly.

When I tell people, we did do that, so you were

like, Talk with someone about your feelings on a text?

Who is this person?

And so fast forward now, we've been through this confluence of a pandemic, a

mental health crisis, not unrelated economic uncertainty.

It's amazing to see, I think, the

truly global cultural transformation in terms of

how this category is viewed, the importance of it, people's willingness

to engage in that conversation and to do something about it in a way that I

certainly couldn't have predicted when I took the role early on at Ginger.

But I like to think that we were one of

many companies who were taking charge and giving people the tools and resources to

realize that this was something that was very important to them.

And Headspace, of course, which was

founded actually around the same time line as Ginger, which really democratized this

concept that people really thought of something as monks

in the mountains doing and brought it really to Earth for people in a way that

was practical and understandable and fun and delightful.

And again, we merged about, at this point, about a year and a

half ago, so just about a third of my journey at the time at Ginger.

And it's pretty amazing to watch the

transformation of certainly Ginger, the legacy company, but

our companies as a whole over the last year and a half.

So I'm super curious about the merger because that's bringing...

How big were the two companies, personal allies at the time?

I think Headspace was about 250 to 300 folks.

Ginger was about 500.

And that's primarily because

many of the staff are licensed clinicians and behavioral health

coaches that are on staff to be able to help serve our members.

The corporate side was a little bit smaller.

We are today around 1100 people.

Big organization. Yeah, it's a big organization.

How similar were the cultures?

Or were they different?

And if they were, how did you mesh

everything together so that people felt like they belonged?

I'll go out and say it's the absolute hardest part of...

Any merger, I'm sure, as you've heard,

even in the best of industrial logic does not make a merger easy.

That's what it comes down to it.

Very similar in terms of mission

orientation and of passion, I would

say, and that you can't replace that.

And so that's been amazing, I think, to

witness people coming together in this way.

Differences were...

Ginger was a San Francisco based company,

very much like a Silicon Valley tech company.

Headspace based in Santa Monica, lots of

incredible talent, streaming, entertainment.

And so you can imagine just like in that sense, quite different in terms

of people's backgrounds, points of view, work that they're doing.

And then if you imagine, what company can you think of where you have

people who produce ME award winning content and also have therapists.

That's really the range of folks that we

have in the company with just a range of both professional lived experience.

And so while the cultures

and I think the ethos behind the cultures are very similar, I think, again, jobs

should be done, but the work is quite different.

And being able to communicate in a way that everybody understands about where

we're going in terms of our strategy, where we want to be as a company.

Our vision means different things to

different people just given how diverse I think our.

Workforce is.

What were some of the things that you did as you started to work on the merger?

It always comes back to values, always, always people and values.

I think it is for certain that there will be areas

of tension, areas of change where we add one process that we do this.

This other team has not. So do we continue to just

ignore that these two things are really different and continue to do them

differently, or we find a way to collaborate and do those together?

And those can be tension fueled conversations many times.

There's enormous tax on the organization when you go through a merger.

And again, if you can get back to putting humans at the center of it,

both the people that we have committed to helping around

the world as well as all of us as people ourselves.

Remembering that we did a merger in the middle of a pandemic remotely.

Wow. It's so hard to do.

It's not like you can throw a big party and everybody gets together and you

don't have the option of doing any of those things.

And so we did some things where, for example...

So one, we spent a lot of time soliciting

input from employees on developing our new set of values together.

And so we did work groups, we brought

specific cohorts together, we did surveys on this so that when we land it on our set

of values, they were co crafted by our employees and by the team.

And

that level of ownership, I think, is incredibly

important for people to feel vested that they're not being told what to do, but

this is inherently actually who we are and how we're going to operate in this way.

And I think it helped us tremendously

in terms of being able to, at the end of the day, have empathy for one another

when we need to make changes or when we need to collaborate on

something and to always in some good intent, which can be easier.

Said than done.

It's so easy to lose the human side, right?

But if you focus on that, it can make it a little bit easier for folks.

Christine, we love to cap interviews, but

first off, thank you for coming on and sharing your journey.

It's been fascinating.

Now that we've reflected and we've had

this conversation, I'm curious, if you could do it all over again, would

you walk down the same path or would you do it differently?

Totally. Totally.

I love being able to connect the dots,

and of course, it's easier to do in hindsight, but so much I think of every

part of my career in my life has helped me to

learn the things that I know today and be able to share that in these conversations

and with my team, including some of the bigger mistakes I think that I made.

It's been an incredible learning experience and it would change.

And Brendan, before you ask that last

question, we got to ask, did you meet John Legend in the Super Bowl ad?

Yeah, I did not. My team did.

It was the pandemic when we shot this.

So one person for my team was able to go. But from what I heard.

Very gracious. That's great.

Brendan, back over to you. Sorry, I just had to ask.

It's because he's from Ohio. That's why, right?

It's from Ohio.

So, Christine, where can people learn more about you?

Where do you want them?

Where do you want to send them?

Yeah, certainly for me

personally, LinkedIn is a great way to find me, get in touch with me.

I love connecting with folks

from all industry, all walks of life, I love taking those conversations.

So find me on LinkedIn and I would love to chat.

Awesome. Yeah, thanks, Christine.

This was fun for me. You're kicking ass and please continue.

It's great. It's so good to see you.

It's so good to see you. I really appreciate it.

Yeah, Christine Evans from Headspace, thanks again.

This was awesome.

Thank you.

Thanks for listening to this episode of the Leadership Backstory.

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Peter Barron, and Brendan Shnider host the Leadership Backstory.