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Each week, Revenue Operations expert Rosalyn Santa Elena shines the spotlight on founders, CEO's and Revenue Leaders from hyper-growth companies and dives deep into the strategies they implement to drive growth and share their learnings through the process.
Rosalyn brings you the most inspirational stories from revenue generators, innovators and disruptors, as well as Revenue Leaders in sales, marketing, and, of course, operations.
Let's unpack everything that optimizes and powers the revenue engine with this brand-new podcast from Growth Forum https://www.growthforum.io
Rosalyn Santa Elena: Welcome
to the Revenue Engine Podcast.
I'm your host, Rosalyn Santa Elena,
and I am thrilled to bring you the
most inspirational stories from
revenue generators, innovators and
disruptors, revenue leaders in sales and
marketing and of course, in operations.
Together we will unpack everything
that optimizes and powers the revenue
engine Growth Forum production.
Are you ready?
Let's get to it.
The role of marketing and driving
revenue has changed significantly.
With the more complex go-to-market
motions, the more demanding buyer
and the volatility of the market.
Being a marketing leader requires
you to be data-driven, focused
on operational excellence and
being 100% in lockstep with sales.
In this episode of the Revenue Engine
Podcast, Jessica Gilmartin, the Chief
Marketing Officer at Calendly, shares
how to be a successful marketing
leader and gives her advice for cutting
through the noise marketing for both
product-led and sales-led go to market
motions and aligning with sales.
She also shares how she
navigated and elevated.
In her career, despite often
being the only woman in the room
and what she does today to ensure
others have the same opportunity.
So excited to be here today with
Jessica Gilmartin, the Chief
Marketing Officer at Calendly.
For anyone not familiar with Cal Calendly,
although I really can't imagine anyone
listening to this podcast wouldn't be.
Calendly is really the scheduling
automation platform that helps
businesses, close deals, build
relationships, and grow faster.
So welcome Jessica, and thank
you so much for joining me.
I am so excited to just share your story
and really learn more about your journey.
Jessica Gilmartin: Thank you, Rosalyn.
It's great to be here.
Rosalyn Santa Elena: Thank you.
Well, let's talk a little
bit about that journey.
Maybe prior to your current
role, um, you've held so many
different leadership roles.
I saw you were at Asana and
Honor and Lighthouse AI and
Google and just so many others.
Um, do you mind sharing maybe more about
your journey and, um, maybe some of
those key milestones that, you know, have
kind of led you to where you are today?
Yes, absolutely.
I,
Jessica Gilmartin: I potentially have the
weirdest journey ever to c m O of a B2B
software company, but I think all, all of
them have been great learning experiences.
So I started as an investment
baker for four years.
What I learned there was a lot
of grit and a lot of resilience,
um, and a lot of powering through
very, very difficult situations.
So I, as difficult as it was, I, I'm
really grateful for that experience.
Um, and then ended up pivoting to
marketing after business school and, you
know, went, went to a couple different
companies and then moved to the Bay Area
and started a chain of yogurt stores.
Which was probably the
weirdest one of them all.
Um, but it, it totally
made sense at the time.
And I think what I learned from
that is, um, just what it's
like to be an entrepreneur.
And I've really taken that
entrepreneurial spirit with me
absolutely everywhere I've gone.
And I think that has
served me incredibly well.
And that's something that I look for
in everybody that works for me is that
owner mentality and that spirit of
agility and, um, just really focused on.
Speed and, um, and, and reacting
quickly to every situation.
So I did that and sold it, and then ended
up stumbling into tech marketing and
kind of have done that that ever since.
And I, I'd say the last really
pivotal experience for me was at a
company called Piazza, where I joined.
I thought a CMO.
Um, but what, what?
I actually joined as our first head of
sales and, uh, my, my day one, my CEO said
to me, okay, you're gonna go out and sell.
And I was like, but I'm not a salesperson.
And she said, well, I need
you to be a salesperson.
So I spent two years selling, and
I think, I can't imagine a better
experience for a marketer than
to, than to sell and have a quota.
And understand what it's like to talk
to customers and try to close them.
And I think it's made me a dramatically
better marketer having done that.
Rosalyn Santa Elena: Oh, I love that.
Talk about resilience, right?
Being thrown into a role
like, well, guess what?
You're gonna be doing this.
And especially, it's not, I mean, sales
definitely is not something for everybody.
So I think that's amazing and that's
really, really great experience too.
Um, and I did know about
the yogurt thing actually.
I, I know I acted a little bit surprised,
but actually I did know about that one.
I was looking at your background,
so I'm happy you shared.
That, um, you know, you joined
Calendly this year, right?
As the Chief Marketing officer,
and it sounds like you actually are
doing marketing this time around.
Yeah.
But, you know, but what, what
interested you in the company and
what brought you to the company?
Jessica Gilmartin: Yes.
Thank God we have an
amazing head of sales.
Nobody's asking me to be
head of sales at Calendly.
Um, so I mean, the number one thing
I think for, for any marketer, the
number one thing that that is the,
the most important thing is to
market a product that you love and
that you personally get value from.
And so there's, there's nothing better
than being able to sell a product that
you really believe in and that provides
value to, to its customers and its users.
And obviously Calendly is that way.
Uh, and you know, everywhere I
go, no matter where I go, when
I tell people that I'm a work
at Calendly, I immediately hear.
How it's impacted their lives, how
they use it, how much they love it.
And that's a, that's a wonderful feeling
to know that everything that you're doing
is actually making people's lives better.
It's easier, it's helping them make money.
It's helping them find candidates.
It's helping them grow their business.
Yes.
I mean, it's just, it's something
that is, is um, really personal for
me to be able to do that, but also do
it at a company that has tremendous
scale, that has a tremendous brand
and that also has huge potential.
You know, we, we are, I, I really
feel, um, so passionately that
we're just getting started.
You know, e even though we
have done so much, there's so
much opportunity and there's.
There's still a big story
to tell and there's still a
big product vision to fill.
And so the combination of having
that product market fit, having
that scale, but having a ton of
opportunities is, is my sweet spot.
That's what I love and that's
what gets me motivated.
That's awesome.
Rosalyn Santa Elena: Yeah, and I
definitely have a story to share around
how it's changed my business for sure.
I mean, I am, I'm a user.
I'm a, you know, a proud and happy, um,
User for sure, for my business as well.
So definitely maybe after the
call I can share that with you.
But, um,
Jessica Gilmartin: thank you.
I love it.
Rosalyn Santa Elena: Yeah.
You know, I think, you know, scheduling
automation or I guess maybe making it
more importantly, making it easy, right?
For those potential buyers to meet
with your business is so critical.
I think we, you know, we as buyers, right?
We, we wanna be able to schedule
and meet with the right people at
the right time, you know, as the
really the leader in the space.
Like what have you seen in the
market, maybe in terms of trends or
maybe how has it evolved and, you
know, where do you see it going?
Jessica Gilmartin: Absolutely.
And, and when to, our founder
started it many years ago.
He, he was really the pioneer.
No one had thought of this.
He was a salesperson.
That was frustrated at trying to do the
back and forth ping ponging of emails.
Yeah.
And so he created this link and
it was this brilliant, incredibly
sophisticated, intuitive, easy
thing, um, that immediately took off.
And, and obviously what's happened
over time is that, you know, lots
of people have created links, um,
and, and we're still the then the
number one, uh, in the market.
But what we've realized is that
the, the needs of our customers
are just much more sophisticated.
And of course their, their
asked are more sophisticated.
And so, The, the big thing that we
are, are working on, and the big thing
that we've created is opportunities
to really serve mm-hmm our customers
with different use cases and with
their more sophisticated needs.
So, you know, if, if you're a salesperson,
um, and you are trying to schedule a
meeting, one-on-one meeting with a,
with a customer or prospect, now you
might want to bring in your manager
and you might wanna bring in your
sales engineer, and you might wanna
bring in your solution specialist
and your customer service support.
All of a sudden that becomes a very
complicated meeting to schedule.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And so
we allow you to do that.
And so that's one really big step.
I think the second, you know, big change
is how integrated different teams are.
So, you know, marketing and sales
and support used to be very siloed.
Now everybody has to work together.
And so we created this routing solution
that we launched a few months ago.
Rosalyn Santa Elena: Mm.
Jessica Gilmartin: Which is really
about how do you as marketers, Enable a
really intuitive, sophisticated system
on your website to allow leads to get
to the right support specialist or the
right salespeople, um, in a way that
will allow them to close deals faster.
And I think the final thing that we're
seeing is that, you know, uh, people
are really kind of tired of tool
proliferation and having to work in 10
or 15 different systems at the same time.
Rosalyn Santa Elena: Yes.
Jessica Gilmartin: And so how do you have.
Something, a, a product that spans
many, many systems and allows people
to work within the tools that they're
already spending their time in.
Whether that's LinkedIn,
whether that's Salesforce,
whether that's Gong or Outreach.
Um, so that they're not constantly
having to contact Switch.
So these are the things that
we spend a lot of time thinking
about and building for.
Rosalyn Santa Elena: Yeah, I love that.
Yeah, definitely tool proliferation.
When you said that, I just felt like a
little bit of, a little bit of anxiety.
But yes, definitely the more that we
can, you know, help our, especially our
sellers, but everybody, any user, right?
Being able to stay in the same
platform and do multiple things, right?
Address multiple use cases, and some
of those challenges in one place
is gonna not only drive efficiency,
but adoption and just better
synergies and better productivity.
So, Definitely.
Jessica Gilmartin: Yeah.
I, I sometimes feel like if you opened
up our heads these days, you would
just see a little ping pong ball that's
just going back and forth because we
spend so much time context switching.
Rosalyn Santa Elena: Yes.
Jessica Gilmartin: And it just, it,
and it really kills productivity
and, and sometimes I just feel
exhausted at the end of the day
with all of the context switching.
So the, the more that we can
do to just create opportunities
for people to stay in a flow
Rosalyn Santa Elena: mm-hmm.
Jessica Gilmartin: Um, I think the better.
Rosalyn Santa Elena: Yeah.
Yeah.
100%.
I definitely agree with that.
Um, maybe along the same lines, I think
about, It's getting harder and harder.
Right.
To kind of cut through that noise and
reach prospects where they want to be met.
Right.
I know as a buyer, you know, as a
consumer, as a buyer, I'm expecting Right.
It's, I have, I'm overloaded
with information kind of
talking about that context.
Switching.
Right.
It's over overloaded with information.
So, you know, I guess what do you
see organizations maybe doing right?
And then maybe some of those things
that they're doing wrong when it comes
to cutting through that noise Right.
And getting to the right
people at the right time.
Jessica Gilmartin: Yeah, I, I
think about this a lot, especially
from the B2B side in two ways.
So one is the outbound and one's inbound.
Rosalyn Santa Elena: Yep.
Jessica Gilmartin: So I think when I,
when I started my career in marketing,
I think you could still have.
A pretty robust and, um,
effective outbound motion
Rosalyn Santa Elena: mm-hmm.
Jessica Gilmartin: With just having SDRs
that are just pounding people all day.
You know, we, that worked for us.
Rosalyn Santa Elena: Yeah.
Jessica Gilmartin: Uh, I don't
think that works anymore, at
least from what I can see.
Rosalyn Santa Elena: Yeah.
Jessica Gilmartin: And I
think it is because there's
just so much noise out there.
So when I think about effective outbound.
I think our job as marketers and
is to work really closely with
salespeople to just have amazing data.
And so when I think about, you
know, how do we give our sales team
really great data to know who are
the right people to target at the
right time, and that is through, you
know, really robust product data.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: Really
good intense signals.
Bringing anything that you can together
so that our sales team has a good
understanding of which of the accounts and
the people that they should reach out to.
So I think fundamentally it is just
moving away from the spray and pray
approach of, Hey, I'm just going to
email lots of people every day and hope
someone responds to, I'm going to email
a very small number of people, but I'm
gonna do it with a lot of great data
and intent and a lot of personalization.
Rosalyn Santa Elena: Yeah.
Jessica Gilmartin: That's kind of on the
outbound side and on the inbound side,
you know, our job as marketers is to.
Bring people into the funnel, which I, and
at a, at a, I say a pretty broad level.
So our job is to really kind
of, um, make sure that we have a
very broad message that goes out
to as many people as possible.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And then, then
when they come to our site, our
job is to figure out how to create
a really personalized experience
for them so that they understand.
Why, you know, our
product is right for them.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And make sure that
they get to the right person as quickly
as they possibly can, and that they have
a really great pre-sales experience.
That sounds easy and logical, unbelievably
difficult, and it's probably where I spend
the vast majority of my time right now.
Rosalyn Santa Elena: Yeah.
Yeah, definitely.
Definitely.
Especially when you're being.
You know, when you're being, uh,
just inundated with information
from all different areas.
Right.
Even, even if we go on to the webs,
different websites, we can see so much
information, but getting to the right
information, meeting with the right
people is just so important and within
a, you know, reasonable amount of time.
Jessica Gilmartin: Yeah.
Especially cause most prospects
send 10, 15 seconds on your website.
Rosalyn Santa Elena: Exactly.
Jessica Gilmartin: And they spend,
they spend 15 seconds engaging
with your ad if you're lucky.
So you have 30 seconds to make
sure that they understand.
What your product does and
why it's valuable for them.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And what's the
right action they should take?
That's not easy.
Rosalyn Santa Elena: Not easy at all.
Definitely.
So I guess maybe talking through that, I
mean, I think that, you know, all of us
are looking to drive more revenue, right?
And I think one of those ways,
especially if they're only spending
15 seconds on your website, right?
Learning about that and kind of leveraging
that product led growth strategy right,
is a great way to engage new users.
Um, you know, if and
when it's right, right.
For your product.
Um, but it's super complicated as well,
especially from a marketing perspective.
So how do you see sort of the marketing
role different in maybe a PLG led
motion versus a sales led motion?
And then what do you think other,
you know, marketers or other
CMOs should really be thinking
about when they have both?
Jessica Gilmartin: Yeah, and, and I,
the, the PLG motion was pretty new to me,
so my whole previous career was really.
B2B marketing and, and sort of more
enterprise, top down marketing.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And then
Asano is really where I learned
about the PLG motion and.
I really underestimated the fundamental
difference between PLG and slg.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And I had to almost
relearn marketing when I was at Asana.
And the great thing is that when it
came to Calendly, it was incredibly
similar and I was able to take a lot
of those learnings and really help
apply it to, to um, to Calendly.
So there's, man, I can go on.
We could, we could spend literally
five hours talking about this,
so I'll try to, I'll try.
Keep it short.
Um, so I'd say one of the, the big
differences between being a, a CMO
of SLG versus PLG motion is that,
With a, with a PLG motion, the CMO
is really actually at the epicenter
of, a lot of these are really in
incre, really strategic decisions
that are happening across the company.
So I have to think not only about
my, the marketing that I'm doing to
influence sales, which is kind of
what I used to do, but I have to think
about what is our product experience?
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: What is our
customer support experience?
What's our activation?
What's our monetization,
what's our retention?
How do we marry the, um, the leads that
are coming in from the product to sales?
Rosalyn Santa Elena: Mm.
Jessica Gilmartin: You know,
how do I support the expansion
business on the sales side?
How do I get really good product
data, um, to sales so that they
have these good intent datas
Rosalyn Santa Elena: mm-hmm.
Jessica Gilmartin: Signals?
How do I think about the, um, trade offs
between people signing up for our product
and people becoming leads so that they can
talk to sales and what's more valuable?
I can go on and on,
but just the complexity
Rosalyn Santa Elena: Yeah.
Jessica Gilmartin: Is at least
a hundred times more with a PLG
motion than with an SLG motion.
And I think that's why I love it, because
you really have to think about the,
all the incredibly difficult strategic
decisions that are happening with
product and sales and CS and finance
in a way that you don't if you are
in a more traditional S L G motion.
Rosalyn Santa Elena: Yeah.
Yeah.
I definitely think, you
know, I think about.
All the areas of revenue, but especially
in the marketing world, at least my
experience has been, you know, I've
worked for several companies that do have
both, um, both a product led, sort of a
self-serve motion, a freemium product,
you know, some type of product led motion.
And then I'll have a
traditional sales led motion.
And I've seen sort of on the marketing
end, just some of that complexity
and some of the change in mind shift.
Right.
Especially if you are a marketing.
Leader who hasn't worked in
that, um, that type of model.
So that's super helpful.
Thank you.
Jessica Gilmartin: Yeah.
One thing also that I, that I, is, that
I did, that I underestimated how hard
this was to make the change is that
in a S L G model, you typically have a
very clear persona that you're marketing
Rosalyn Santa Elena: Yes.
Jessica Gilmartin: And selling to.
And it's, it, it's pretty
easy and straightforward.
You know, when I, when I.
When I was at Wildfire, we
sold to social media marketers.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And
directors of marketing.
So you knew exactly who to target, you
knew exactly the message to share all the
materials, all the conferences to go to.
It was very straightforward.
When I was at Piazza, we sold to
recruiting and it was the same thing.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: When you have a PLG
business, You're just kind of trying
to beat the bushes and you're trying
to get as many birds to fly into the
net as possible, and so you may end up
with 15, 20 different types of people
Rosalyn Santa Elena: mm-hmm.
Jessica Gilmartin: That engage
with your product and sign up.
And so you can't market and sell to
15 to 20 different types of people.
And so you have to make a lot of
really hard decisions and trade-offs.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: About, you know,
who is going to be your persona.
You can't have more than three or four.
Right.
And who's, you know, is and, and
how are you going to segment it?
Are you going to segment by.
Use case.
Are you gonna segment by function?
Are you going to segment by level?
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And then how do
you, when they, when they, when you do
advertising, when you do conferences,
when they come to your website, when
you provide sales materials, when
you segment your sales team, how do
you make sure that you are, you know,
segmenting by those appropriate personas?
You have the right use cases and
the language for each of them.
Um, and you can speak to
them without sacrificing the
other parts of your business.
So that, that really is where a lot
of this extra complexity comes to.
Rosalyn Santa Elena: Yeah.
Yeah.
That's great.
That's a great point.
Thank you.
Um, you know, one of the topics I guess
that comes up frequently, and I know I'm
doing a lot of context switching right
now too, cause I wa I have so much that
I wanna ask you and learn from you.
Um, but I think that, you know,
maybe shifting a little bit, cuz
one of the topics that comes up
really frequently in my work is
to how to drive better alignment.
Right between sales and marketing, um,
you know, and because you've done the
sales role, you've done the marketing
role, you know, you're, you're probably
really good at driving that cuz you
have that empathy and understanding.
But you know, maybe what has worked
for you right, to have better
alignment and synergies with sales.
And do you have any
advice for other people?
Jessica Gilmartin: This is probably
the question I get asked the
most, which I find really funny
because I find it really easy Yeah.
To have alignment.
And I think it's, it's so interesting
that it, it is such a hot topic.
And so number one is,
is having empathy Yeah.
For sales.
Um, and, and I make sure that
with my team, I don't allow
any negativity towards sales.
So, you know, one thing that I hear
all the time is marketers complaining
that sales doesn't work their leads.
Sales doesn't do this,
sales doesn't do that.
And my perspective, you know, that I have
a few things that I share with my team.
Number one is, you know, if, if you,
um, don't have to worry about feeding
your family because you didn't make
your quota, then you cannot complain.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: You know,
we get paid whether or not we
hit our numbers, they don't.
So let's have a deep level of empathy
for the fact that they are trying
to, you know, feed their family.
Um, the second thing that I share is that,
Salespeople are really smart entrepreneurs
that run their own business, and they
are trying to figure out the easiest and
most efficient way to hit their number.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And if they're
not working our leads and if they're
not, uh, supporting the programs
that we are giving them, it means
that we are not doing our job.
It means that they, they are telling us.
Implicitly that they
don't value our programs.
And so we need to either change
our programs or we need to change
the way that we're messaging to
sales so that they see value.
So it's on us.
Um, so that's, that's number one.
Uh, the second thing is we have
to speak the same language, so we
can't be talking about webinar.
Um, uh, attendees for leads.
Sales does not care about that.
They care about the
dollars in their pocket.
So we, they, they're talking
about revenue pipeline.
We need to talk about revenue pipeline,
and we need to show how what we're doing
is driving revenue and pipeline for them.
Uh, and then the third thing is we
need to create our plans together.
Rosalyn Santa Elena: Yes.
Jessica Gilmartin: So, you know, I,
I have so many times seen where a
marketing team will put together a plan.
And then they'll just tell the sales
team what they're doing and then
they're surprised and angry when
the sales team doesn't follow along.
I'm like, well, if someone just
came to you and told you how to do
your job, you'd be pretty upset.
And so, you know, we, what, what we do
on my team is we create our calendar,
um, our proposed activities and our
strategy, we share it with the sales team.
We ask for their feedback.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And once they
have given their feedback, and
we agree on the plan, And that is
our shared accountability plan.
Rosalyn Santa Elena: Yep.
Jessica Gilmartin: So we are accountable
for delivering those programs and
they're accountable for supporting them
because they've said they're valuable.
So if they've said, yes, we
think events are valuable, then
I'm gonna hold them accountable
for following up on event leads.
And so I think it's that
mutual accountability and
communications is really important.
Rosalyn Santa Elena: Yeah.
Yeah.
Speaking all my language,
um, my background is all on
the revenue operations side.
You're speaking my language alignment.
And you know what's funny is that
I actually think sometimes it
is, I wonder why it's so complex,
because as you pointed out,
it's really fundamentals, right?
It's the fundamental things of
good communication, empathy,
you know, driving alignment,
making sure people buy in, right?
And that mutually agreed plan, and
that goes for goals and language
and you know, the extra actual
plan that you're gonna execute.
You know, it's just driving
that alignment, making
sure everybody's on board.
Um, but it is definitely,
Jessica Gilmartin: yeah, it's so easy.
It's so easy to point fingers and
it's so tempting to point fingers and
especially when marketing and sales
are so inextricably linked and we
all, we each depend on each other.
And so it's very easy to say, well, I,
I made these great programs, but you
didn't follow up with the leads And
sales says, well, I followed up with
the leads, but they were terrible.
And that's, that's not helpful to anybody.
And so, you know, I think it, it
really is about understanding,
being curious, asking why.
Uh, and, and trying to get
to the, the heart of what's
working and what's not working.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And recognizing
that everybody is trying to do the same
thing and trying to do the right thing.
Rosalyn Santa Elena: Yeah.
Oh, you're speaking my language.
I feel like we rehearse
this ahead of time.
Being curious, asking why, you know,
getting in the same boat a lot of times
is just like, you know, everybody in the
same boat instead of everyone row, you
know, in their own separate little boats.
It's so important.
Awesome.
I love that.
Um, so let's shift gears
again a little bit.
You know, and I think that, you
know, at this point, you know, I'm,
at some point I'm really hoping
that this is not even a topic.
It's not relevant to discuss, but.
I think unfortunately in today's
world, we're still seeing revenue as
primarily still more male dominated.
I think it's changing, but it is still
primarily, and I think especially as
you look at executive leadership roles,
you also see less female leaders.
You know, as a rev ops leader, for me,
you know, there's been many times where
I'm the only woman in the room as well.
So, you know, as a woman in a
C-level, you know, revenue role at a
technology company, um, what advice
do you have maybe for other women
who are looking to, you know, elevate
their career and maybe continue
to move up that, you know, ladder?
Jessica Gilmartin: Well, I can tell
you, having started my career in
investment banking, I am very familiar
with male dominated workplaces.
Rosalyn Santa Elena: Yes.
Jessica Gilmartin: Um, I think
there was 90% men and 10% women.
And, uh, and, and I would say that
there was a lot of, there was a
lot of trauma there, to be honest.
There's a lot of experiences there that
really impacted me and took me a long
time to sort of unwind in my psyche.
So I am, I am deeply understanding
of this issue, uh, and still work
working through some of that.
Uh, so I'd say, you know, I think
one, one of the things that I think
a lot about and, and I think I've
learned myself having made a lot of
these mistakes is, is you have to be
confident and you have to be direct.
Yes.
And you have to figure out ways.
To be confident, you have to ferre
out ways to be direct, even if
it feels really uncomfortable.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And I think, you know,
it's, it is one of those things of like,
you've gotta fake it till you make it.
Right.
And, and I think it's, it is so hard
for women to be, in particular, to be
in environments where they don't feel
a hundred percent confident and they
don't feel like they belong in the room.
And I think just giving yourself the
permission to fake that confidence
and eventually you will be confident.
Um, I say that the other thing that I
think a lot about, and I, I tried, I
think earlier in my career to mirror
a lot of the sort of the, the patterns
and the communication and the behaviors
of the, of the men that I worked with.
And it didn't feel right to me,
but I tried because I thought that
that was the right thing to do.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: And so when I became
me and when I gave myself permission to.
Be softer and be kinder, um, and
be more human and be more female.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: That actually
is when my career took off and that
was when I was more successful.
So I think you can learn.
From the best of what other people,
what, what you're seeing from
other people, but don't feel like
you have to be them and don't feel
like you have to be just like them.
Rosalyn Santa Elena: Yeah.
I love that advice.
That's really good advice.
I love that.
Um, yeah, I definitely
think that's great advice.
I have to kind of soak that in
a little bit, but definitely
thank you for sharing that.
I appreciate that.
Jessica Gilmartin: I'm curious,
what do, what do you think?
What are some things that you've done?
Rosalyn Santa Elena: Yeah,
I absolutely think so.
I'm the mirroring piece.
I, I don't know, you probably saw me
kind of nodding my head and smiling
because yes, I do think that earlier in
my career definitely felt that way as
well because there wasn't anyone in the
room, you know, sort of look like me
or, you know, just different, I think.
And so you try to sort of fit in, but then
you realize at some point in your career
it's like, look, I'm, I'm, that's not me.
That's not my style.
And then figuring out what works for,
you, know, what works for you and how you.
Feel comfortable so that you can be
confident and then you can actually,
you know, excel in your career.
Um, but yeah, definitely can,
definitely resonates with me as well.
Yeah.
Um, I think the other thing that I,
you know, a lot of times when I get
asked that question, um, and this goes
along with sort of that confidence
and being comfortable with yourself
is also getting kind of that being
okay with being uncomfortable, right?
You talked about kind of
fake it till you make it.
But I also think it's like, it's
okay to be uncomfortable because
that's really where you grow, right?
That's, that's, I think that's
the big growth zone is when you
are in that uncomfortable zone.
So I wish I, you know, I guess that's
one of the things that I probably wish
I did more of when I, earlier in my
career, which just take more risks
and put myself in more of those, you
know, what might be perceived as an
uncomfortable situation, um, versus.
You know, kind of sitting back and
kind of letting others take the lead.
Jessica Gilmartin: Yeah.
And, and I think that, you know, it's
one of the really interesting things
when I was an investment banker and
I would go into a room and there
would literally be 30 men and me.
Rosalyn Santa Elena: Yep.
Jessica Gilmartin: Is I would immediately
go and find a chair in the corner.
Rosalyn Santa Elena: Yes.
Jessica Gilmartin: And I would sit there
and it was just the thing that I did.
And I remember when I
worked at Dell and it was.
There were a lot of men there too.
It was, it was more men than women.
And I would do the same thing.
And I remember there being people
that said, no, come sit at the table.
Literally they told me to
have a seat at the table.
Rosalyn Santa Elena: Yeah.
Jessica Gilmartin: And, and
that, that meant a lot to me.
That meant a lot to have somebody
said, no, you, you belong here.
You deserve to be here
and come up and sit here.
And that's something that
I try to do a lot now.
Whether, whether literally
or metaphorically, Is how do
you, is is leaving space for
other women or, or anybody else
Rosalyn Santa Elena: mm-hmm.
Jessica Gilmartin: That feels
uncomfortable or that feels different
or, or, um, you know, it, it seems like
they are, they want to participate, but
they something that holding them back
Rosalyn Santa Elena: Yeah.
Jessica Gilmartin: Is like, how do
you help them get a seat at the table?
Rosalyn Santa Elena: Yeah.
Yeah.
I love that, that, um, you know,
as I think about the Revenue
Engine and then this podcast, I.
Always hope that others will be
able to learn, you know, how to
accelerate revenue growth, right?
Empower that revenue engine.
Um, maybe if there was like one piece
of advice, right, one thing that you
would give to any revenue leader or maybe
another CMO, you know, kinda that one
thing that makes all the difference when
it comes to revenue, what would that be?
Jessica Gilmartin: This is gonna be
the least sexy answer that you've
ever heard, but I actually believe it.
It's really building a
great infrastructure.
Um, and a great base,
Rosalyn Santa Elena: oh, you're
speaking my language again.
Jessica Gilmartin: I know that maybe this
is the most sexy thing you've ever heard,
but, you know, we, we, as marketers,
we wanna do all the great things.
We wanna do the super, we wanna
do the Super Bowl commercials, we
wanna do the billboard campaigns.
We wanna have millions
of dollars in ad spend.
We wanna have the, the great messaging.
But you, you, if you don't have the
underlying processes, the system,
the data, the accountability, um,
you, you will not be able to make
it successful because you cannot
figure out if it's working or not.
Rosalyn Santa Elena: Yep.
Jessica Gilmartin: I think that
that's just so important in this
day and age is that you can't just.
Um, build something or launch something
or spend something and then continue
to have free reign if you can't
demonstrate why or, or why it didn't work.
Rosalyn Santa Elena: Right.
Jessica Gilmartin: Um, and so it is
all the nuts and bolts of the o of
the plumbing and the data and the, um,
alignment that you have to do in order to.
Get the opportunity to
do the sexy, fun stuff.
Rosalyn Santa Elena: Yep.
I love that.
Oh my gosh.
You're like, so speaking my language,
I feel like, like I'm sponsoring.
I'm sponsoring your guest appearance, like
alignment and plumbing and infrastructure.
You're just speaking my language.
I love it.
Love it.
Jessica Gilmartin: Yeah.
Rosalyn Santa Elena: Thank you so
much for joining me, Jessica, but as.
As we wrap up before I let you
go, I always love, you know, to
ask two things of all my guests.
So one, what is that one thing
about you that maybe others
might be surprised to learn?
I know we touched on the yogurt
piece already, but maybe, maybe
there might be something else.
And two, you know, what is the
one thing that you really want
everyone to know about you?
Jessica Gilmartin: So, probably the thing
that others would be surprised to learn
is that the, between the first and my
second year at business school, I was a.
Semi-professional poker player.
Rosalyn Santa Elena: Oh, nice.
Jessica Gilmartin: Yes.
Rosalyn Santa Elena: Wow.
Jessica Gilmartin: I haven't played in
many years, but that was really fun.
Um, and, uh, and I, and I learned
a lot talk again, talking about
spending a lot of time with, with men.
It was, it was me and a lot of
men and I think they were always
surprised when I beat them.
Rosalyn Santa Elena: Yeah.
Jessica Gilmartin: So that was fun.
Rosalyn Santa Elena: Awesome.
Jessica Gilmartin: I love that.
Yes.
And then probably the, the thing that I
would want everybody to know about me,
and, and maybe, I think this goes back
to what we talked about before about
what it's like to, to try to be yourself.
Rosalyn Santa Elena: Mm-hmm.
Jessica Gilmartin: Um, is that I think you
can be really kind and you can be really
thoughtful and empathetic and be a great
leader while also being really direct
Rosalyn Santa Elena: mm-hmm.
Jessica Gilmartin: And being
results oriented and holding
people to, to high standards.
So I, I try to do both and I believe
that the kindest thing you can do
is to create an environment where
people are doing their best work.
And they know exactly where they stand.
So that's, that's kind of something
that I have learned over time is
how to balance those two things.
Rosalyn Santa Elena: Yeah.
Oh, I love it.
I love it.
That's exactly, almost just so many words
and so many thoughts that you're sharing
just really, really resonate with me.
Um, so definitely thank you so
much for joining me, Jessica.
I really appreciate you sharing so
many great insights, really great
advice, and just learning from you.
It's been amazing.
Thank you.
Jessica Gilmartin: I've, I've loved it.
Thank you so much.
Rosalyn Santa Elena: Thank you.