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August 22, 2025 19 mins
Ashley's career in radio has evolved over the last 17 years when it comes to the positions she's held - with her most recent position as of almost three years ago - running the most listened to country radio station in Florida as the Director of Programming and Brand Strategy for US103.5 & iHeartTampa.

In this position, Ashley works with all of the record labels out of Nashville when it comes to learning about new artists, new songs, new projects & introducing them to the Tampa market. That's where Sarah Headley comes in. Sarah's "street title" amongst the industry is a "record rep" for Big Loud - but the official title is "Director of Promotion" - promoting, what, you may ask? Music. Artists. Sarah travels her region sharing the latest music from Morgan Wallen, Miranda Lambert, HARDY, ERNEST, Lauren Alaina, Ashley Cooke - and SO many more incredibly talented artists who are signed to the Big Loud record label based in Nashville.
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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome back to another episode of Sunnyside. This is so
exciting because Sarah, you're literally one of the first guests.

Speaker 2 (00:07):
I'm honored, Like, I'm so excited to be here.

Speaker 3 (00:10):
Well.

Speaker 1 (00:11):
I tried to do a lot of the episodes at first,
kind of solo because I didn't want to have to
depend on guests all the time. But I thought, oh
my gosh, Sarah, you're going to be in town because
you live in Nashville, and when you were going to
be in town, I'm like, she's somebody I would want
to have on the podcast. Let's see if we can
make this happen in the timeframe what we have. And
I'm so glad you were down for it.

Speaker 2 (00:30):
Obviously, I'm excited that you are having me on. I
listened to the first episode the other day after we
talked to him, like, this will be fun.

Speaker 3 (00:37):
Oh good.

Speaker 1 (00:38):
Well, I think a lot of people that have listened
or follow me on social media over the years have
known my job in radio, in country radio, and they've
gotten to see a lot of the really cool things
that I've gotten to do and be a part of.
And you have been a part of so many of
those things because they involve your artists. So that being said,
I want to shut up because I think people would
love to hear what your job is.

Speaker 3 (00:59):
Like, what it even is, and how you even got
into it.

Speaker 2 (01:02):
Yeah, first off, I never knew this was a job.
So technically, I guess my job is called the director
of Radio Promotion for the Southeast. So my job is
getting our artist songs played as much as humanly possible
on the radio to go number one, which is super fun.
And that involves, you know, traveling a lot and seeing
these songs being played in arenas and stadiums and all

(01:26):
of that. So getting to see like how it affects
country music fans in real life and talking to people
like you on a weekly basis to get it done.
So it's super fun. And I never knew this was
a career path, but here I am.

Speaker 1 (01:40):
I know, And that's what I've told my followers and
listeners before, Like I never wanted to work in radio.
I didn't know this job even existed. So going back
to you being a rep specifically for honestly some of
the if not the biggest artist in our format. We
can say Morgan Wallen, Yeah, we're not going to go
down the rabbit hole of details of anything, because that
could be a whole nother podcast. Yeah, just in general,

(02:01):
if your experiences and things you've gotten to do. But
everyone from Morgan Walland to Earnest to Ashley Cook to
Lauren Elena, I mean you your roster of artists is
so different on artists experience, their success, and so the
fact that all of those artists are people that you
work with, Well you just explain a little bit about
why you even have to come into markets and meet

(02:23):
with radio stations.

Speaker 2 (02:24):
Yeah, well, I feel like, like you said, they're all
on very different levels in terms of where their career is,
and especially these newer artists, it's hard to break through sometimes,
so uh, coming to station visits and even bringing them
with me so that they can form those relationships. You know,
some of these people those relationships six years down the road,

(02:47):
like their life looks a lot different than it did
in that first initial meeting when I came to Tampa,
you know what I'm saying, Like, I remember when we
met with Ashley Will was this like two years ago, Yes,
two years ago, out getting coffee by the water. That
was so much fun. And that was before I mean,
that was before she ever had her first number one.

Speaker 3 (03:06):
That's true.

Speaker 1 (03:06):
We were at the Getaway and they have there's a
little coffee place or the Patrona cafe. Yeah, shout out
in Saint Pete. But Ashley Cook, we were sitting there
just as Your Place was about to be released on
the radio that went number one for her.

Speaker 3 (03:19):
Yeah.

Speaker 2 (03:19):
No, It's so fun to watch that sort of stuff
happen and see it see it grow, like hearing that
song and seeing even your artist reactions like hear their
song on the radio for the first time. It's so exciting.
I don't know, And I grew up listening to country
radio and artists like this, and so now being a
part of it and getting to spread you know, their
music with people and and all of these markets. It's

(03:42):
just super fun. And I never knew that there was
like this back end to it. Okay, you kind of
like when you're listening to the radio, sometimes you think
that it just it just magically happens, But there's so
much work that goes into it.

Speaker 3 (03:52):
And it's so true.

Speaker 1 (03:53):
And I'm glad you brought that up because that's something
I've never publicly talked about and explained. Like people will
be like, why do you guys play this song and
why is this song played so much? It's like that
really has a play into artist's songs. What are people
liking right now? And obviously then you go and crossover
totally into the other world where you've got the streaming platforms,
the Spotify's, the Amazon Music's where your artists and that's

(04:16):
a whole other world whether they have a ment success.

Speaker 2 (04:19):
And it's crazy and this is above me too, but
like we look at those numbers, like across any platform
and see how things are reacting. So that's that kind
of drives, especially where I am. We look at the
data to see what we should be bringing to people,
like what's gonna work, what's gonna react?

Speaker 1 (04:36):
Yeah, And I think it's funny and I'm glad that
we're talking about this because so much of our social
media pages, like even on yours, when people see you
at your artist show and you traveling, like it's all
the highlight reel.

Speaker 3 (04:46):
It's all the cool stuff that we get to do.

Speaker 1 (04:48):
But I don't think people realize that we're actually looking
at data.

Speaker 2 (04:50):
But it's there are so many facets of our jobs.
And it's so funny because I was talking to my
mom yesterday, and she works at the hospital in our
local hometown, and so she sees everyone. Okay, so she'll
be like, oh, I ran into so and so and
they just said that they love watching your Instagram and
all this stuff. I'm like, that's so fun. But like
you guys, you know, it is a grind. There's a

(05:13):
lot more that goes into it than just what you
see on social media, for sure.

Speaker 1 (05:17):
And you and I are alike in the fact that
I don't think we ever want to complain because we're
really so grateful. But like we were talking right before
we started recording this podcast, like you're only going to
be home for or even like a couple months ago,
you were home like once the entire month.

Speaker 2 (05:32):
Almost, Yeah, Like I think I'm home five days this month.
But that is like how lucky am I to be
in that position? You know? And I know everyone I've
seen this on social media a lot lately, but it's
like I don't have to I get to yeah, And
I think it's about the framework of that, like I
get to be here today. I'm in Florida three times
in like a week and a half, but I get

(05:53):
to do that, and I get to see people. You know,
it's fun. So yeah, it's an exciting time. It's a
busy time, but we're very thankful to be here.

Speaker 1 (06:02):
And it helps too because we've formed a friendship over
the years, You and I. Yeah, and it helps when
you're able to do that in the industry that you
work in, where you find colleagues or people that you're like, Okay,
they are coming in for business, but there's also a
respect and a relationship. We literally swam with manatees.

Speaker 2 (06:20):
We got up at like four or five am to
go drive two and a half hours to swim with
manates I forgot that we got up at early. It
was so early, but it was so much fun. And
that's that's one of the things that I love about
this job, is like you get to make so many
memories like that that like why, like how is that
even a thing? But we did it and it was
fun and I don't know, you never know where it's

(06:43):
going to lead you.

Speaker 1 (06:43):
It's true, And I feel like this is such a
great segue into what we were talking about. And I
was like, We've got to talk about this on a
podcast because Sarah, obviously you've just talked about like how
much you travel, and it's a lot of times it's
your weekends, it's nights, there's concerts, the's events, it's a
lot of great stuff. But it's like when does anyone
screw he's in their vacations in personal time. Yeah, and
you were telling me you just had a huge trip

(07:04):
to Europe and it was like your first major trip
to Europe recently.

Speaker 2 (07:07):
Yeah. So I just got my passport in the past
few years. One of my best friends in the whole world,
she lives in London. She grew up between like all
the places, and so she convinced me to get my passport,
like right before COVID, I feel like, and then COVID
hit of course. So we've been planning this girl's trip
with all of my girlfriends from college. We used to

(07:27):
do it every year. Now we do it every few
years where we all come together. We all live everywhere,
so like Boston, San Francisco, Charlotte, Miami, London, and we
all find a place and meet there. And so this
year we decided to meet in France.

Speaker 3 (07:43):
Casual casual.

Speaker 2 (07:45):
Yeah, And so we started in Paris for a weekend,
which I had never been to before. Was me neither
The only place I had been was London and that
was in December. So I have never been anywhere cool
really until then. And so we we spent some days
in Paris and then we got a big airbnb in
the south of France and like this super cute little

(08:07):
town that was like you could just walk down to
the town every day and get like.

Speaker 1 (08:11):
Bread or like whatever. I don't know, we would never
do here in the US. I walk down to the
corner and get bread.

Speaker 2 (08:17):
No, no, no, I like in the mornings, I would
walk down and get like a croissant and coffee and
just sit by the water. It was. It was so nice.
I loved it.

Speaker 1 (08:26):
But we were talking yes about and this is another
area where we're both like we've had very career similar
career paths where you have a lot of you know,
early success and I think we can call it success
when you were at an early age and you find
yourself in a career that you have a lot of
freedoms independently, like you get to pick where you go

(08:47):
on vacation. Right now, you're not married, no kids, You're
able to do all these things. So you get used
to a certain level of privacy and comfort and at
this Airbnb.

Speaker 3 (08:57):
You guys, you were sharing a room.

Speaker 2 (08:58):
Yeah, let me preface us by saying, I love my friends.
I'm not opposed to sharing rooms you guys. But that
being said, you know, I live by myself. I travel
a lot for work. I think I took like one
hundred and forty flights last year. So like I'm in
a hotel room by myself a lot. Okay, So going
on vacation and sharing a room, that's a different experience,

(09:20):
you know. And I love I love my friends so much.
But we're also in our early thirties now, so you know,
everyone is in different life stages. I've got friends who
are married with children, and then I've got friends who
are single like me, And I think we're kind of
in that like in between limbozone where like the single
friends get lumped together. But we're also like we're we're

(09:43):
thirty two years old.

Speaker 1 (09:44):
Right, and I know, and you're almost like, hey, like
I'm not I'm not the scum of the earth just
because I'm single without kids. I remember a lot of
times people will and not like that you're being treated badly.

Speaker 3 (09:57):
Yeah, almost just like oh you don't need.

Speaker 1 (09:58):
The nice room because yeah, which I get yes, of
course the families with.

Speaker 2 (10:02):
Kids, familiesued to have more space. They need more space,
but it does get a little sticky sometimes this went. Look,
I was not stuck on a pull out couch, so
you know there have been those times. I'm not we
have surpassed that level, but you know, we're all used
to having our alone time. And I think in order
and I my friends will tell you I did. I
did say something this trip. I think the rose got

(10:24):
to me a little bit at one point and I
was like, you guys, we need to have a discussion,
like moving forward. I think that we all need separate bedrooms,
like we all. I think that that is a fair assessment.

Speaker 1 (10:37):
And you know, you know what's funny is Sarah was
telling me the story on the phone last week and
I was like, oh my gosh, that's literally this whole
situation is why I did not just go on vacation
with my husband and bonus son, because they were going
to his buddy's lake house.

Speaker 3 (10:51):
And I was so excited.

Speaker 1 (10:52):
Because I originally was going to go, and then I realized.
I asked him, I'm like, wait, does everyone have their
own room? And he was like ooh ooh, and I'm like, wait,
is this like an air mattress situation? Like I'm two,
I'm thirty seven. My back hurts, yes, sometimes, like I'm
not not on an air MAT's not ideal, no, And
I felt I felt bad at first cause I also
didn't want to seem like Diva.

Speaker 3 (11:13):
E, like oh sorry, any of my own space.

Speaker 1 (11:16):
But it definitely was more so not an age where
I'm used to my own space.

Speaker 2 (11:20):
I was afraid of sounding Diva E too, And honestly
I might have a little bit because at that point
it was a rose. We were in the south of France.
It had to be done. But I find and I
found on this trip, I'm like, I need to recharge,
and I need like I need to go back to
my room and just watch tiktoks for a little bit
and just have silent time, you know, in order for
me to be the best version of myself. I know that.

(11:43):
I know that now, and like three days it's fine,
but like a week and a half, I'm like, then
it's you know, yeah, yeah.

Speaker 3 (11:49):
You get to that point, I think too.

Speaker 1 (11:51):
Again, you're used to traveling, being in your own hotel room,
being able to escape Irish exits. Yeah, yeah, yeah, and
even they can be that your best friends in the
world and you love them to death, it doesn't matter,
like totally. My husband TJ's aunt and uncle live up
in Virginia in an area called Meadows of Dan and
it is the cutest little country town. There is nothing there.

(12:13):
You have to drive into town to go to another
little super cute town called Floyd, Virginia. And they were
so hospitable, but I was so out of my element
inside their home. And then I feel like you always
have like a pressure of you're in someone else's home. Yep,
so you kind of have to do what they want
to do.

Speaker 2 (12:31):
See, that's the thing. I think all of us also
are at a point where we do everything in our
own way, you know, so like when you're sharing a
bathroom or a bedroom, like the way that I might
organize my stuff, which by the way, is not organized
because I am a hurricane are everywhere? I kind of yeah,
like I it's a little bit everywhere. You guys, I'm sorry,

(12:54):
it just is what it is. But you know, if
you share a room with someone who's not like that,
then that could really put them on edge. And you
know what, I'm sorry, but that's the way I am.

Speaker 1 (13:03):
You probably never noticed it much really until you got
into a room where everyone else's stuff was like neat
and tidy.

Speaker 2 (13:09):
Yeah, yeah, I mean I do. If I'm somewhere for
an extended period of time. Now, I do sometimes try
to hang up my things, you know, to make it
feel a little bit put together. Yes, but that's not
the norm because normally I'm somewhere for like a night.

Speaker 1 (13:21):
So I was just gonna ask you that, because I
come to Nashville like three or four times a year
for different meetings, and that's the most I travel for
work specifically, like for work work.

Speaker 3 (13:31):
Yeah, and when I get there, do you do this?

Speaker 1 (13:34):
I take all the stuff out that I'm gonna wear,
and I do hang it up specifically for those events.
But like if I'm on vacation, my stuff's wadded up
in my suitca.

Speaker 2 (13:41):
So same same. I'm throwing things around, just digging in there.
I'm like, I know that that black tank top is
in here somewhere. Okay, this happened to me. I packed
these exact black linen pants and I'm wearing right now. Okay,
I packed them. I thought I packed them. I looked
everywhere all the whole France trip couldn't find them, and
I'm like, well, I have to search. I have to

(14:01):
buy new black linen pants. I went in every h
and M, every Zara trying to find linen pants long
enough to fit my body because I'm six feet tall.

Speaker 3 (14:09):
As you say, Sarah's tall. We need to paint those yes,
six feet? Are you six fun?

Speaker 2 (14:13):
Yeah, okay, so it's very hard for me to find pants.
So imagine how distraught I am that my black linen
pants are not there. I finally find some that are fine,
whatever I buy them. I get home. My black linen
pants were in my bag the entire time, but they
were at the bottom and the bottom of my bag
is black, and so when I went to Linerck, yeah
it looks like the liner. I was so upset.

Speaker 3 (14:35):
That's frustrating, especially because you wanted to wear them.

Speaker 2 (14:36):
Yeah. I wanted to wear them so badly, and they
were there the whole time.

Speaker 3 (14:40):
And maybe that's like, okay, maybe I should unpack my bag.

Speaker 2 (14:42):
Yeah, I need to be better about that. But still
I do my bag honestly. At home, sometimes my suitcase
is kind of half packed at all times.

Speaker 1 (14:51):
No kidding, you were literally, I mean you just told
me that you were at home for like a night
this week before you flew back down here to Florida.

Speaker 3 (14:57):
Yeah, so do you even do laundry? Do you even wait?
Or do wait until all of your trips are gone.

Speaker 2 (15:01):
I've been doing so much laundry lately. It's like I'm
home for a night, I'm going to do a couple
of loads and then I'm going to hang them up
and they'll be they'll be good to go when I
come back, you know. But my toiletries and everything are
mainly just always together because they always they always have
to be ready.

Speaker 3 (15:15):
Yeah, They're just in your two go bag all the time.

Speaker 1 (15:17):
Yeah. So when you leave here, like like, let's talk
about go back to your job a little bit before
we say goodbye, because we actually have to do business.
When you leave here, you will go visit other radio
stations literally, whether it's in Florida, Georgia, the Carolinas, and
as far as shows like just kind of tell us
what the rest of your year looks like.

Speaker 2 (15:38):
Uh, the rest of the year is pretty busy. So
I've got I've got some big tours uh this fall,
which is super exciting. I've got double booked dates galore
in the fall. So then in that instance, I'm like,
I've got to have coverage you guys, because i can't
be in two places at once. But I'll be hitting
a lot of a lot of the Southeast and just

(16:00):
on the road a lot.

Speaker 1 (16:02):
You've been NonStop though since you got out, Like I
kind of like to put this out there because I've
really started this podcast about like especially women finding their confidence. Yeah,
in career, and I know you and I we both
still have things to learn.

Speaker 3 (16:15):
We're still learning.

Speaker 1 (16:16):
I think everybody, no matter who you are, even if
you're a president at a company, like still learning things.
But any young women out there music industry are not
that are kind of entering the career field now, especially
this generation. Like do you have any advice or like
the hustle it took for you to get to where
you are?

Speaker 2 (16:33):
Yeah, I so, like I said before, like I didn't
realize that this is a career path I was going
to take. But what I did for four years was
network my frickin' butt off, and I did everything. I
would take a week off from work to go be
a temporary media staff worker at CMA Fest and work
the CMA Awards and like I would take solo trips
to Nashville just to like grab coffee and drinks with

(16:55):
whoever would talk to me. I was messaging everyone and
their mom on link. It was NonStop, So like, just
put yourself out there because you never know who might
help you. I met someone. I ended up landing a
gig and doing social media for a festival in Charlotte,
and I met a radio rep backstage, and honestly, meeting
her is what led me to where I am now.

(17:17):
But I never would have known that.

Speaker 3 (17:18):
Yeah, so you wouldn't have known the job even existed exactly.

Speaker 2 (17:21):
I had no idea until I met her.

Speaker 1 (17:23):
I love that because that's so many people's path because
I had mentioned like I had no idea what I
wanted to do in college.

Speaker 3 (17:29):
I just wouldn't have got a degree. But I didn't know.

Speaker 1 (17:31):
I never was the type that wanted to be a
nurse or a teacher. I didn't have any specific field.
But not until I started working in our field was
I like, oh, that's a job.

Speaker 3 (17:40):
That's a job.

Speaker 1 (17:41):
So I love that you put yourself out there and
knocked on doors.

Speaker 2 (17:45):
No matter what, you have to be willing to put
yourself out there. And do things that other people don't
want to do because I what I ran into is
everyone that I was applying for jobs against they went
to Belmont, they did music business. I already had the
internships and had all the connections that I didn't have,
So I had to work twice as hard to even

(18:06):
get my foot in the door anywhere. So that's one
thing that I really want to hit home for people,
is like it's you don't have to have the experience
there to get into it. I think you just have
to have the passion. And that's that's what I encourage
everyone to do. I want to talk to more people
even at like you and c my alma mater, because
no one ever told me that was a job. I
was going to be a journalist, and no one told

(18:28):
me music was an option. It is an option. You
just got to go after.

Speaker 3 (18:31):
It, no kidding.

Speaker 1 (18:32):
And then you'll learn about all the different things you
can do exactly by networking.

Speaker 3 (18:35):
Yep, well, I'm so glad.

Speaker 1 (18:37):
One of my very first guests, Sarah Hadley, do you
want people.

Speaker 3 (18:39):
To follow you on instagramure follow your travels?

Speaker 2 (18:41):
And what?

Speaker 3 (18:42):
Sure?

Speaker 2 (18:42):
I mean? You can? It's at s Headley on Instagram.
Or Shedley Shedley however that way. Yeah, my friends make
fun of me for that one. But I'm there on
Instagram and I'm gallivanting all over the Southeast all the time.

Speaker 3 (18:57):
I love it.

Speaker 2 (18:58):
Well, thank you, thank you for having us.

Speaker 1 (19:00):
We love that people are getting a little glimpse behind
the curtain of the music industry here. So that's another
episode of Sunnyside. Make sure you're following us at Sunnyside
with Ashley on Instagram.
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