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July 11, 2024 56 mins

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When you think of your career journey, does it look anything like you thought it would 5, 10, even 20 years ago? 

Get ready to be inspired by the remarkable journey of Jenn Southan, Senior Director of Customer Support at Olo, in her podcast debut. Jenn takes us through her transformative five-year tenure at Olo, marked by navigating the tumultuous waters of a global pandemic, the excitement of a company going public, and the complexities of multiple acquisitions. Discover how she transitioned from outsourced support to leading an internal team, all while offering invaluable advice on setting non-negotiables, establishing boundaries, overcoming imposter syndrome, and embracing career pivots.

Jenn's story is a testament to resilience and reinvention, as she shares her experiences of taking significant time off to raise her children and then re-entering the workforce with TeamSnap. From growing the support team at TeamSnap to facing unexpected layoffs and rebounding with a role at Olo, Jenn's journey is filled with lessons on respecting new roles, drawing motivation from colleagues, and rebuilding passion in the face of adversity. Her narrative emphasizes the importance of a balanced approach to career growth and the power of glowing recommendations from peers to reignite one's professional drive.

But the inspiration doesn't stop there. We explore how Olo's intentional hiring practices and support for internal mobility foster a thriving and adaptable workplace culture. Learn how encouraging shadowing, cross-departmental projects, and career coaching can reduce imposter syndrome and boost employee satisfaction. Jenn's story highlights the significance of confident female leadership and the societal challenges women face, all while embracing the "Ownership Era" of her career. As we wrap up, we leave you with a call to action to take bold steps in your own career journey, ensuring you're always moving toward personal and professional greatness. 

Don't miss this transformative conversation with Jenn Southan—it's bound to leave you motivated and ready to make great things happen.

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“Change will not come if we wait for some other person, or if we wait for some other time. We are the ones we’ve been waiting for. We are the change that we seek.”
- Barack Obama

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Jenn Southan (00:00):
And I still remember and I think this is
where just a lot of myphilosophy came from you sign,
they call it a corporate creed,which sounds very like fancy,
but it is this thing, and yousigned it and you framed it and
they put it on your office wall.
But the very first thing wasalways deliver more than the

(00:20):
customer expects.
And I still remember that andthat is heavily influenced.
You know kind of how I look atthings.

Sarah Caminiti (00:32):
How many times have you thought there has to be
a better way?
Welcome to Epochal Growth, apodcast where we invite industry
leaders and change makers whothought that very thing and
realized that, yeah, a betterway to lead or to grow or to
build does exist.

(00:53):
And once they trustedthemselves enough to discover
what's possible, they createdthe foundation for a new era
that's revolutionizing thelandscape of success, for a new
era that's revolutionizing thelandscape of success.
The word Epochal refers to thesevery moments in time, because
when you commit to being better,the impact will last for

(01:19):
generations to come.
I'm your host Sarah Caminiti .
Join me to uncover practicalinsights and strategies that
will empower you to be thechange that you seek.
This is Epochal Growth.
I'm so happy that you're here.

(01:52):
Hello listeners, welcome toEpochal Growth.
This is an episode with a lot offirsts.
This is not only our guest,Jenn Southen's first time
appearing on a podcast.
This is also the first timethat I am publishing the podcast
all by myself.
Up until Su pport Driven, hasbeen kind enough to be
publishing the podcast for me,and I have been feeling brave
and have decided to take overthat piece myself, and it was

(02:16):
perfect timing, becausesometimes the universe brings
you the right people at theright time in more ways than one
, and that's exactly whathappened with Priscilla at
Buzzsprout.
She's the head of customersupport there and I am so
thankful for her.
I am so thankful for everyoneover at the Buzzsprout team for
helping me get set up.
Priscilla also has a fantasticpodcast.

(02:39):
It's called Happy to Help.
It's a customer support podcastwith incredible content and I
definitely recommend.
You won't be disappointed.
This isn't even an ad.
I just love celebrating greatpeople doing great things, and
that is Priscilla and her teamover at Buzzsprout.
So I'm so grateful for you guys.
Thank you for everything.
We have an exciting road ahead.

(03:11):
Speaking of Buzzsprout, you cannow find Epochal Growth pretty
much anywhere you could possiblyimagine.
I'm talking Podcast Index, I'mtalking iHeartRadio, amazon
Music TuneIn, podcast Addict.
The list goes on and on.
So stream Epochal Growthwherever it is that you like to
stream podcasts.
Make sure you're following thepodcast.
Sometimes I may even sneak in abonus episode, and the best way

(03:34):
to be notified is if you'refollowing the podcast.
And if you haven't subscribedto YouTube, please do.
I'm putting some great clips inthere, so when you don't have
the time to listen to a fullepisode and you just need a
reminder of what's Jenn possible.
Go to the Epochal GrowthYouTube page and find those
snippets from the incredibleleaders that have shared their

(03:56):
stories with Epochal Growth.
For today's episode, I want youlisteners to think about what
you thought your career wasgoing to look like.
I'm talking.
Think about what you thoughtyour career was going to look
like when you were 20 years oldand how, when you were 25, what

(04:17):
you thought success was going tolook like changed, and when you
were 30 and 35, and so on andso on.
And when you were 30 and 35,and so on and so on.
Some key takeaways from thisepisode will be identifying what
your non-negotiables are, howto set those boundaries,
navigating imposter syndrome andembracing a career pivot.

(04:37):
I've gotten to know Jen throughthe Voices Carry women's group.
I've always admired how shearticulates her experience with
so much respect and honesty.
It tells you a lot about whoshe is as a leader and why it's
no surprise she's as successfulas she is.
Let's jump into episode 11 ofEpochal Growth Stepping Back and

(04:57):
Stepping Up.

Jenn Southan (05:13):
I'm Jenn Southan.
I'm the Senior Director ofCustomer Support at Olo.
Olo is a restaurant techcompany that is a platform for
many of the major brands thatyou know and love to utilize for
online ordering.
I actually today is myfive-year, as we call it,
oliversary, so I have been withthe company for five years,
thank you, and I just recentlytook over the support team from

(05:34):
my previous manager, who hadbeen at the company for 17 years
Wow and she is on a sabbatical,living her best life For her
well-deserved after 17 years.

Sarah Caminiti (05:47):
Yeah, absolutely Well.
Congratulations to you.
What an awesome period ofcareer transition and just
excitement for you.

Jenn Southan (06:00):
Yeah, it's been a great ride.
In the time that I've been here, we've experienced COVID, which
, in the restaurant industry,was a bit of a roller coaster.
Wow, the company went public.
We have acquired a couple ofother companies, so it's been
nothing if not exciting, yeah.

Sarah Caminiti (06:22):
What a ride you've been on within that
five-year period.

Jenn Southan (06:27):
Yeah, absolutely, not to mention that support had
been outsourced and I was, Ibelieve, the second class of
people that they hired in tohelp with standing it up
internally, with standing it upinternally, so that has also
been super fun.

Sarah Caminiti (06:55):
Yeah, that's.
That is a very interesting likeintro into this space,
especially after what you'veshared with me about your career
journey.
What an interesting space toenter.
From that regard too, I don'tknow if you want to give a
little bit of an overview ofwhat brought you to Olo and how
things were in the past, butyou've had a really cool career

(07:15):
trajectory.

Jenn Southan (07:17):
Yeah, absolutely.
It's been nothing short of aride, for sure.
It's been nothing short of aride for sure.
I had decided to stay home withmy kids for a while, so I took
a step out of the workforce forabout eight or nine years and so
when I went back into theworkforce, I started working for
this company called Team Snap.

(07:38):
They are a youth sports teammanagement and I was the first
person they hired outside oftheir founding team to do
support.
It was a great setup for me.
I was working remote.
They were based out of Boulder,colorado, and worked with them
to grow the team to about 25.

(08:01):
Unfortunately, at that point Igot laid off, went to work for
another like super small startupand that one did not work out
so well.
We just had kind of differingvisions, if you will.
But upon leaving there I justrealized how burnt out I was

(08:22):
between you working for astartup and growing that team
and then kind of moving rightinto this other startup.
And you know, everyone knowskind of startup life is a little
crazy.
There aren't traditional workhours, typically, and things
like that.
So I was.
It was quite a ride.

(08:42):
When I decided to leave thesecond startup, I took a couple
months off before evenconsidering looking for another
job Good and then decided I justwanted to go back to being an
individual contributor.
As I told my soon-to-be bossduring our interview, I said I

(09:04):
just want to come to work, do agood job and, at the end of the
day, close my laptop right, notbe on call, not have all the
pressure and responsibility.
And thankfully she took me atmy word and hired me into this
IC role, and I think she did itwith an eye towards the future,

(09:25):
knowing that the team was goingto grow, and so it was a really
great experience working for herand getting my passion for the
job back.
I really enjoyed kind ofgetting my hands dirty again.
I really enjoyed kind ofgetting my hands dirty again and
really just kind of getting toknow the product.

(09:54):
Olo itself is a prettycomplicated product, so it was a
great kind of trajectory for mewithin the company and through
kind of her demonstration ofwork-life balance and what that
could really look like, I wasable to just get excited about
leading a team again, and sowithin Olo I moved into like a
tier two more technical role.
Prior to staying home I hadworked in more technical roles

(10:19):
software development, thingslike that.
Oh, wow, okay.
And then I moved into aleadership role, helped build
out all of our tier two teamsthe way they are now which are
focused on products.

Sarah Caminiti (10:38):
And yeah, here I am now, because your work
history before you joined OLOwas so perfectly connected to
what was needed in OLO.
But the cool thing that yougave them was I want to build
this as an IC instead of as aleader, which is a totally

(11:05):
different approach, and I canonly imagine what opportunities
presented themselves by lookingat things from that lens and
structuring things from thatlens rather than from like an
overarching space.
Did you know when you wereentering into this role that you

(11:30):
were going to have theopportunity to shape things and
influence things as much as youhave?

Jenn Southan (11:38):
No, I had no idea.
Like I literally was, like Ijust want to be in IC, I want to
do a good job.
I knew that I would bring someexperience to the table.
So my boss that hired me onshout out to Maureen.
She had not worked in customersupport before.

(12:00):
She had hired a manager thathad, and so she had to lean on.
But I knew that I would bringsome you know experiences that
maybe neither of them had.
At the same time, I was alsovery cognizant of the fact, and

(12:23):
probably overly so, that I likenot to step on toes or, um, the
one habit to break was I was soused to making the decisions,
yeah, that it was hard not tojust like make decisions in the
moment.
But, um, again, it just goesback to kind of being cognizant
of what my role was and andbeing respectful of those that

(12:49):
were in those roles and, and Ithink it it worked out well, I
have to say, over the years.
You know, I think Maureen wouldsay she learned as much from me
as I did from her.

Sarah Caminiti (13:15):
So it was.
It was really a greatpartnership and worked out
really well over to buildingsomething and still being laid
off, which I'm sure that musthave been an incredible shift in
perspective of what it actuallymeans to work for a company.

Jenn Southan (13:35):
Yeah, that was the first time I had experienced
that and kind of the way it allwent down was a bit of a shock
too.
They had announced somecompany-wide layoffs, like the
Friday before, and I was notpart of that.
I was supposed to go to anevent.
There was some miscommunication.

(13:56):
I ended up not going.
Apparently they didn't includeme in that because the CEO
wanted to tell me himself.
I had reported to him for anumber of years and so whereas I
thought shoo, you know I madeit through that wasn't the case,
and so in the end I'm glad Ididn't see him face to face when

(14:18):
he told me, because it wasupsetting and unexpected.
But you know, ultimately,ultimately it turned out for the
best.
So you know, no hard feelings.

Sarah Caminiti (14:31):
No hard feelings , no, I know, but I'm sure it
was a journey to get to thatplace, especially knowing what
you did.
Like you, you built it and thatis a huge win for you and
something that I hope that youallow yourself to be very proud
of and acknowledge what it wasthat you accomplished, Because

(14:54):
not very many people can saythat they do that, especially to
scale it the way that you didthat's.
That's not an easy task.

Jenn Southan (15:01):
Yeah, it was.
It was a great team.
And if I'm ever like feeling alittle down on myself or having
that, you know, impostersyndrome, when I left TeamSnap,
a lot of my colleagues wrotesome really glowing
recommendations for me onLinkedIn and so I go back and I

(15:22):
read those and I'm like onLinkedIn.
And so I go back and I readthose and I'm like, okay, yeah,
I got this.
Like I can do this.
We had a really great group ofpeople that work there.
We still stay in touch.
We have a Slack channel orSlack group that we're all still
in, so it was a uniqueexperience.
It was a really great companyto work for and, yeah, I'm very

(15:43):
proud of the team that I'vebuilt, seeing some of the people
that are still there and whatthey're doing, seeing people
that have moved on to othercompanies and what they're doing
there.
Like you know, when Jenn youcan see someone else succeed and
realize that you had like asmall part in that, it's pretty
satisfying for sure.

Sarah Caminiti (16:02):
Definitely, definitely.
I think that's one of the bestpieces of being in our industry,
of being a customer focusedprofessional, where our goal is
to help others be successful,and how that translates to
leadership and connects, andyou're able to see, not just a

(16:26):
this is an email that happened,someone was really happy and it
was great.
No, you get to see, like, thetrue personal impact that your
approach to connect with themgives them, and that's not
surprising from what I know ofyou, jen, that you had that kind
of an impact on your team thereand they continue to, just, you

(16:48):
know, support you and praiseyou for that.

Jenn Southan (16:51):
Yeah, thank you, I appreciate it.
I've always kind of lived bythe mantra, you know, do unto
others as like, give people thesupport that you would want to
receive.
Um, and ultimately, you know,yes, we have a job to do, but

(17:12):
we're all human and you don'tleave that humanity at the door
when you come to work, um, so ifyou're having a hard day and
it's just not working out orthings aren't going well, I want
to know that Right Cause, um it, it affects you as as a person
and a human being, and noteverybody is a hundred percent

(17:36):
every day.

Sarah Caminiti (17:38):
No, no they're not supposed to be, because that
wouldn't be uh, wouldn't be anyfun.
My North Star is the goldenrule.
It is how I handle support,exactly the way you described it
.
It's how I lead my teams.
It's how I mentor others.
It is how are you feeling inthis?

(18:00):
How can I put myself in yourposition?
How can I put myself in yourposition and in difficult
conversations?
That has proven to be one ofthe greatest gifts of having
that be so foundational.
Have you found that to be trueas well?

Jenn Southan (18:15):
Yeah, absolutely.
I think, particularly as youget a title, that means
something more in anorganization or is higher,
people tend to be afraid of you,and whenever anyone new joins
the team, I always tell themlike look, everybody makes

(18:35):
mistakes.
There's not going to be anyonewho doesn't.
There's not going to be anymonth, year, whatever where you
don't make one and it's okay.
All I ask is that you one takeownership of it.
Like accept the fact that youdid it, um, and learn from it.

(18:57):
That I mean that that's reallyit.
Like make it right if you can.
If If not, we'll figure it out,but just learn from it.
Like just don't keep making thesame mistake and that's it.
And that really has kind ofserved me pretty well, in that
people are not afraid to saylike oh, hey, I think I might

(19:20):
have screwed up here.
And then you sit down and youhave that conversation of like
okay, what happened?
What do we need to do to fix itand what do we do so it doesn't
happen again?

Sarah Caminiti (19:32):
Yes, yes, that is the biggest opportunity for a
shift in the relationship ofsomeone that is in a leadership
position and anyone, even ifthey're not on their team
directly.
If you can create a spacesomething that I always ask
anyone that I'm working with,whether in my company.

(19:54):
I mean, I even asked my husbandit's, why did you choose to do
it this way?
And it takes a little while forpeople to understand the
sincerity behind it, regardlessof how explicitly I tell them I
really am coming at this right.
But it takes the ownership outof it, like that guilt piece out

(20:19):
of it, and it puts it into theprocesses and improvement, and I
love that.
That is exactly what you do foryour teams, because you reduce
the chance of so much just issueand fires to put out, because

(20:40):
people aren't afraid to say thisis what I did, this is how I
went about doing it, because ofX, y, z, and now let's take this
as a chance to reevaluate.

Jenn Southan (20:53):
Yeah, absolutely.
Is it just a trainingopportunity?
Is it an opportunity to updatedocumentation because something
wasn't you know, something hadchanged, or whatever the case
may be, it's.
I mean, I don't think I've everrun into a case where someone
has done something maliciously.
So you know, I don't know whypeople often get treated as if

(21:18):
it was the case.
It's, yeah, again, just aboutlike kind of owning up to it,
accepting the responsibility.
I am a big believer inaccepting responsibility, but
beyond that, like okay, what dowe need to do now?
Let's learn from it, let's moveon.

Sarah Caminiti (21:36):
Yes, yes, it is so much faster, so much less
painful.
And I'm an overthinker myselfand if I let things sit, I stew
and it becomes a way bigger dealthan it ever needed to be.
And if you create that kind ofa foundation, then you can have

(21:58):
those conversations immediatelywithout some ominous.
We need to have a talk in threedays about something, maybe,
kind of.
I won't tell you what it is.

Jenn Southan (22:10):
I'm also a big believer in immediate feedback,
right, Like why wait three daysBecause that's just going to
give someone anxiety and puttingmy neuroses on full display.
I have anxiety, I am anoverthinker.
If there's a worst casescenario, I've got five of them
in my head and so it's like ifsomething happened, it's like,

(22:33):
hey, can we check real quick,you know, and just be like, hey,
this is what I noticed, youknow, and kind of take the
conversation from there and notmake it a big deal.
I think when it becomes thislike scheduled, you know, formal
conversation and there aretimes for that, for sure, Sure,

(22:55):
but just kind of everydayfeedback is not one of them.

Sarah Caminiti (23:00):
No, no, it's.
I mean, you are definitely akindred spirit and I'm so happy
that the folks that listen tothis podcast will be able to
hear your approach tocommunication and the reason why
it can be this way and why it'sso helpful to talk about these

(23:22):
things and say that it's okay todo it this way and it does work
, and you are definitely proofto that.
So I'm so glad that you broughtthat up.

Jenn Southan (23:33):
Yeah, thanks, thank you, it has served me well
.

Sarah Caminiti (23:38):
And I do wonder.
So, when you joined OLO and youcame into a space where you
weren't the leader, you weren'tthe one that was finding these
mistakes and having theseconversations how was the
dynamic with you and your bossand the rest of the folks in the

(23:58):
department?

Jenn Southan (24:00):
You know I've been very fortunate that it was
always really good.
Um, we you know not to brag,but I am we hire some amazing
people here at Olo and they'reall very like conscientious
people, always wanting toimprove.
That's what I look for whenhiring people, more so than like

(24:25):
technical skills necessarily,unless something specific is
needed, necessarily unlesssomething specific is needed.
And I think we all just cameinto it knowing we were building
a team and that we had theopportunity to do something
special.
There were some people on theteam that came in with like

(24:45):
certain skills, like with a POSsystem, because we work with
restaurants and that's needed.
There was someone else who hadbeen a leader and had a lot of
Zendesk experience.
She now leads our support andCX ops stuff, and so it was just
really really collaborative andthankfully, you know, maureen

(25:11):
and the other gal who was amanager on the team, like they
didn't have egos, they knew theydidn't know it all and so they
were willing to listen and youknow kind of factor that into

(25:35):
decisions they were making.

Sarah Caminiti (25:38):
It sounds like you created a space that was
true to your values, true toyour experience, but you had
support in such a great way fromyour, who understood the power
of everything and beingintentional in how you hire is
one of the most important thingsthat you can do.

(26:00):
Especially, I feel in supportbecause there is such a higher
rate for turnover and it is aspecial type of person that
enjoys this work for a longperiod of time.
What was it in the hiring at Olothat was different than the

(26:23):
hiring at the other places thatyou worked?

Jenn Southan (26:28):
Honestly, I don't know that it was terribly
different from when I worked atTeamSTOP.
I used a lot of the samephilosophies there and was very
fortunate we've been veryfortunate at Olo as well to not
have I don't want to say wehaven't had a lot of turnover at
Olo.
We have.
However, it's been almostentirely internal moves.

Sarah Caminiti (26:52):
Oh, that's a turnover then.

Jenn Southan (26:59):
Yeah, it's turnover on our team, but they
moved on to other positions andthat's kind of another way that
we lead is by understanding whatpeople's career goals are and
helping them get there get there.
But honestly, I think in bothplaces the companies had such a
good reputation of being a greatplace to work that it made it
easy to hire good people.

(27:20):
And I think reputation onlytakes you so far.
But being able to speak to themabout, like, how we we deal
with feedback or how we helppeople move in their career, or
how we help people get you knowtraining opportunities or

(27:42):
whatever the case may be, that,I think, demonstrates that we
are invested in them as a personand not just as a number or a
you know seat to fill, if youwill.

Sarah Caminiti (27:58):
Yeah, it's a different mindset and it
translates into how eachindividual contributor, each
member of your team, startstheir day.
It's a foundational piecestarts their day.
It's a foundational piece and Ilove hearing that this is
happening where you are and thatyou've been able to continue to
foster that as you've growninto the leadership role that

(28:19):
you've recently moved into.

Jenn Southan (28:22):
Yeah, thanks, it has been great.
I mean, I'm just thinking backin my head of all the people
that have kind of moved throughour support team.
I had, of all the people thathave kind of moved through our
support team and it's excitingLike we had people move not just
into like more technical roles,like our developer engineering
team, but also into CSM rolesand deployment managers.

(28:43):
We had one person no, I'm sorry, two people move into like our
people ops team and so just lotsof different opportunities that
came because we listened towhat they wanted to do and
didn't get territorial aboutthem.

(29:04):
Right, because you can eithersupport someone in what they
want to do and help them growwithin your company, or you
cannot and they will leave yourcompany, correct?

Sarah Caminiti (29:19):
Yeah, that is a perfect way to articulate it,
and it is something that youdon't see actually happening
happening, and sometimes it'sbecause it's not possible, maybe
because it's a small startupand they don't have the
resources for movement or thosesort of training situations.
But what do you have at Olothat allows these sorts of paths

(29:48):
to be explored?
Is that what it's always beenfor everyone on the team?

Jenn Southan (29:54):
I think so.
Most of the opportunities arethings that come up internally
and working with other teammembers.
You know, if you want to becomea deployment manager at Ola,
which means you're workingdirectly with these brands,
helping them get up and running,there's not really a training
class you can go to for that.
What I encourage people to dois go talk to people on those

(30:18):
teams, spend a few hours half aday, maybe a couple of different
times shadowing them.
Look and understand what the jobreally is.
Don't just make the leapthinking that's what you want if
you don't know what it is yet.
And then if you do that and youenjoy it, then let's talk about

(30:40):
it.
And maybe it's taking on aproject or two or working with
them or sitting in on kickoffcalls.
Whatever the case may be, it'sjust helping them, like, get
their feet wet, show that theydo really have an interest there
and that they're capable ofdoing the job.
Then when a job opportunitycomes up, it's almost a no

(31:02):
brainer, right.
They know the company, theyknow the product, the other team
knows what they're getting inan employee and it it really
just is an easy, easy sell, ifyou will.
It's not even a sell, no, it'strue, and it also I'm.

Sarah Caminiti (31:21):
I feel like that would eliminate a lot of the
imposter syndrome that wouldprevent someone from moving
forward with pursuing it,because you've given them space
to explore.

Jenn Southan (31:33):
Yeah, I would hope so, as someone who still
regularly experiences impostersyndrome.
I don't think it ever goes away, but I mean I would hope so.
And even I remember having aconversation a few months ago
with one of the managers of oneof my tier two teams and he was

(31:55):
considering applying for thisproduct role or product manager
role, and I was like OK, great.
I was like are you really sure?
Like that's what you want to do?
Do you know what the day?
And he was like no, and I said,well, why don't you like look
into it a little bit?
Like I'm happy to support you,but like if you take this other

(32:19):
job opening, you can't just sayoh I'm sorry, it's not what I
thought it was, and come back.
And he did, it ended up notworking out and and he, I think,
is happier where he is now.
But you know, same thing appliedis what I've told other people,

(32:39):
though.
Like, if you still want to lookinto it, like let's find a way
to get you involved.
There are ways to do that.
That, you know, yes, is sometime away from your day to day,
but you know we'll makeallowances, we'll, you know,
make it happen, and but he seemsto be happy where he is now, so

(33:00):
that's all good, yeah, no, thatis good.

Sarah Caminiti (33:02):
And the grass is always greener is something
that everybody experiences fromtime to time, and in the support
industry at least.
For when I began in this space,it was sold as this is your
introduction to the company andyou're not supposed to stay here
.
And then, with the startupworld happening and support

(33:27):
becoming an actual career with aplace in the greater ecosystem
of impact within the company,things shifted a little and it
wasn't as easy to admit that youwere curious about something
else and you wanted to learnabout something else.

(33:49):
Because you committed to beingin support and finding that even
like ebb and flow of.
I want to support you, but Ialso want to support you to stay
here If this is what makessense for you.
That's new.
That's not something thatreally exists very, very often,

(34:10):
and I love hearing that not onlyis it something that's working,
obviously, but it's somethingthat you're committed to as a
company and growing it andlearning from it as you go.

Jenn Southan (34:27):
A lot of it came from just my own career path.
Right, I kind of alluded to itearlier, but I have a degree in
information systems.
So when I came out of college Iwas doing IT support and then
moved.
I worked for a governmentcontracting firm, because I live
in the DC area and everybodyworked for a government
contractor at some point.

(34:47):
And so I moved on to a projectat one point where we did
everything.
We did the requirementsgathering, the software
development, the maintenance,the testing, the deployment,
support, like soup to nuts.
We did it all and it wasprobably the best experience I
could have had because I saw somany different aspects of it and

(35:11):
I moved roles even within thatteam.
I started out doing like justdeployment and training and then
I picked up some of thesoftware skills.
Then we did like a wholerewrite and I was on that
software development team andthen I ran the support team and
it was just a lot that I wasable to try in a very short

(35:33):
period of time.
It was after that project thatI decided to stay home with my
kids for a bit and take a stepback out of the workforce.
And then I found the role withTeamSnap, which was for a
customer support specialist, andwas able to step into that.

(35:55):
But you know, having gonethrough kind of so many
iterations myself, I understandlike, just because you make a
decision today, two years fromtoday, you're not the same
person.
Decision today, two years fromtoday, you're not the same
person and so expecting you tohave the exact same wants and

(36:16):
needs is unreasonable.
We do ask people to stay in therole for a year, which seems
very reasonable, yeah, and thenbeyond that you know it.
That's when we started havingthe conversations about what
else they might want to do, ifanything, some of our folks have

(36:38):
chosen to move into leadershipand have taken on like manager
or associate director roles.
Some want no part of leadership, and that's okay too.
We've created roles for themthat are, you know, allow them
to kind of keep growing in theirtechnical skills and seniority.
It just it's ever evolving, andthat's one of the things that I

(37:00):
really love about OLO.
They've been around for a verylong time.
I think it's 19 years now.
Oh and yeah, we just wentpublic in 2021.
Is that right?
Yes, 2021.
And so we've had to make thischange to a public company.

(37:25):
But we still have a lot ofthese like startup mentalities
where you know, try, things failfast, right, and and it's okay
if things don't work out.
So it's been a really uniqueposition to have that.
You know, we certainly havesome other, some things that are

(37:46):
more structured now becausethey have to be, but, um, you
know, generally it's still verymuch the same kind of um, core
values and and philosophy, sinceI've been here five years now
no, that says a lot.

Sarah Caminiti (38:05):
It's I.
It's interesting that you weresaying how you're allowed to
feel and try things and thatstartup mentality hasn't really
changed, because this issomething that I've noticed has
come up a few times inconversations I had in places
where people feel like they areable to lead the way that they
want to lead because of theenvironment around them and the

(38:27):
culture around them ofexperimentation, because there's
only so much that you can dowhen you are the leader of of a
company I mean out of a company,of of a department to create
the space that you want tocreate for your team.
If the company lives a verydifferent world, that bubble

(38:48):
it's, it's not it's not going tostay intact for too long and
the longevity that happens whenthey create that kind of a space
as part of the culture anddon't lose it as they grow and
make that not only somethingthat like actually happens, but
they make it known that this is,this is something that's
important for a reason andthey're going to do what they

(39:11):
need to do to to continue it asbest they can.
Um is not talked about enoughhow important it is to create
that kind of a space.
Coming from the consultingworld, where you have a very set
path of what is needed and youhave that feeling of you don't

(39:35):
actually work for the companyyou know they brought you on as
a consultant.
How has that translated withthe failure and the
experimentation that that yousee in these startup
environments?

Jenn Southan (39:48):
Again, I think I was like really lucky with the
companies that I've worked for.
So I was employee number 77when I joined this company out
of college, so it was also stillvery startup-y, right.
It was um.
We got a lot of contracts underlike small business association

(40:09):
and things like that Um, and soI feel like it was not as much
of a bureaucracy as it as itcould have been Um, and even
though we had contracts with um,these government agencies, we

(40:31):
still always felt like we werepart of the company.
And I still remember and I thinkthis is where just a lot of my
philosophy came from you signed,they called it a corporate
creed would sound very likefancy, but it is this thing and
you signed it and you framed itand they put it on your office

(40:52):
wall.
But the very first thing wasalways deliver more than the
customer expects and I stillremember that and that is
heavily influenced.
You know kind of how I look atthings I, so my husband works as
a government contractor still,okay, and we have conversations

(41:16):
a lot and I'm just like, wow, Iam so glad Jen Like I don't
still get in that environmentbecause I think, as lucky as I
was, things have changed and youknow everywhere you go, money
is tighter.
Getting money for fundingwhether it be like private
equity, from the government,whatever the case may be is

(41:39):
getting harder and harder, and Ithink having to work within
those constraints is I would notfare well these days
constraints, I would not farewell these days.

Sarah Caminiti (41:55):
No, I hear you, I definitely hear you, and
looking at your career and thechoices that you've made in your
career, it's obvious that youhave made it so.
Part of just every decisionthat you make is rooted in your
values, your companies that youchoose.
You're not only drawn to thembecause of their values, even if

(42:16):
you don't know that they'rethose values, but then they're
also drawn to you because ofyour values and the match that
that has.
And you've been lucky, yes, infinding places that has allowed
you to operate the way that youshould be operating.
But you, jen, have alsoobviously been such a bright

(42:38):
light in these places that theyknew that they had to continue
to let you be who you and findways to enhance that and spread
that.
Um, because it's very easy,especially when companies are
growing, to say they are doingone thing and do the exact

(43:01):
opposite, even if they werewonderful in the very beginning.
And you are evidence that therelationships that you build,
the just like empowerment ofthis is right and it works, and
staying true to that but thenalso allowing yourself to leave

(43:22):
and giving yourself permissionto say this is not the right fit
is testament to who you are asa person and the kind of impact
I'm sure you are having on theother people that that you work
with, especially women, becauseyou are an important person to
have in this world and I'm gladyou're in leadership because

(43:44):
what you're doing tricklesaround and people thank you.

Jenn Southan (43:48):
Thank you so much.
That was very sweet.
I really appreciate that.
I think you know, particularlyin like the support driven group
there are so many strongleaders in support.
When I was working at TeamSTEPPI kind of waxed and waned with

(44:14):
my participation there, but itwas so wonderful to find a
community that has a lot of thesame values and beliefs.
Personally, coming to work aswho I am, it's easy, Like it's
just easier.
Like if I had to put on thislike persona to come to work,
like who wants to do that?

(44:36):
Unless you're an actor and I'mnot.
No, um, so it just yeah, like,oh, who am I supposed to be
today?
no, this is not me, um and andthis, like I talk to my team
members and lead team meetingslike this too, sometimes I have
this like ditzy blonde momentand I'm just like, oh sorry,

(44:59):
like brain fart it happened.
I don't think we can sit there.
And you know, when people puton this like uber professional,
professional front, like they'reperfect and things like that's
not real and that's not me andyeah, that's too much work.

Sarah Caminiti (45:22):
It is a lot of work.
It's a lot of work.
It's exhausting, I'm sure, andyou've been able to solidify
yourself as just owning who youare and seeing.
I mean, this is just it and I'mgoing to do my work well and
I'm going to treat people kindlyand we'll talk about it if

(45:43):
there's a problem, but you allowyourself to be the adult.
I think is what it really comesdown to.
If you approach things in a waythat is even keeled and direct
and there's no personal maliceor any sort of vendetta behind
it, intentional or not, you showother people, whether they're

(46:07):
on your team or not, that thisis how you should approach these
situations.
This is how we're able to growtogether in these situations.

Jenn Southan (46:18):
Yeah, yeah, absolutely.
And I think one thing that Iparticipated in with OLO last
year that helped me growtremendously was a program they
had it's actually called Growand we had like this online

(46:42):
learning platform that we couldutilize.
They got us a career coach forlike six months and we also had
like a group meetup andexercises and stuff.
And I think for me, the reallygreat thing about that program
was not like this is how youshould be a manager, and it

(47:05):
wasn't like black and white,this is how we do management at
Olo.
It was like here's some of theprinciples we live by and you
know, um, let's talk about howthat works for you and how like
you do that.
And then even the career coachwas so helpful because it's

(47:30):
someone that is truly like,impartial and you're able to
talk through and bounce ideasoff of like.
I had not utilized one beforethat and did not realize how
invaluable they are, and so Iwas really appreciative that
they kind of put the investmentinto a program like that.

(47:52):
We're actually trying to getthem to do it for leaders
earlier in their career, sobefore they become like, because
originally it was like forassociate director level and
above, and then they opened itto managers.
We would like to see it evenlike people that want to become
managers, or very early in theirmanager career.

(48:15):
So we'll see TBD on how they'redoing it this year.
That's very cool.
That's very cool.

Sarah Caminiti (48:22):
Is that what shifted your like?
Because you didn't want to dothis, you didn't want to lead,
you didn't want to be in thisposition.
And now look at you you're asenior director.
What was?
I know that your manager, yourboss, really gave you the space
to to explore this, coming backinto a leadership role, but what

(48:46):
was it in the journey that kindof let you do this?

Jenn Southan (48:52):
Honestly.
So that was really what kind ofgave me the confidence to say
yes, like I want to take overthe team when you leave and kind
of take on this new role.
I got back into leadership.
It was probably like seriouslyback into leadership.

(49:13):
About two and a half years agoso about halfway into my journey
, I had started up one of thetier two support teams.
So I was kind of leaning moreinto my technical skills and
enjoying that and, honestly, Imyself had considered taking on

(49:35):
or applying for a product role.
I have always had a keeninterest in like, where the
customer and the product meet.
Um, that's one of the things I'msuper passionate about is like
voice the customer from supportand getting information back to
the product team.
But, um, so I I had applied forthis product position.

(49:59):
I ended up not getting it, butit was really a blessing in
disguise because as thatposition evolved I realized like
I did not take my own advice,like I hadn't really looked at
like the day to day of it andall of that.
But what it did make me realizeis that I really still enjoyed

(50:23):
support and I still reallyenjoyed kind of building teams
in.
However that looked, whether itbe like just the team I was on
that kind of expanded to tiertwo as a whole and building out
new teams there and building outnew teams there, and now we're

(50:45):
kind of at this inflection pointwith the full support team in
that, you know, we'reintroducing some like AI tooling
and automations and some otherproduct enhancements to make
things more self-service, and sothe team is also kind of at
this inflection point.
So I'm excited to kind of helpthem build and grow and change

(51:06):
through this process.

Sarah Caminiti (51:08):
so what an exciting time for you.
And, uh, your career hasbrought you to this point.
I mean, you were supposed toget back into this space and
pull.
You're pulling everything fromevery job that you've had, and
I'm sure even that time that youwere with your kids.
I mean, you learn a lot aboutleadership when you're working

(51:28):
with small child.
But, yeah, like it all hasbrought you to this new space,
which brings me to the finalquestion of what era are you in
now, or what era are you movinginto?

Jenn Southan (51:48):
I think, if I had to label it anything, I think I
am moving into what I would calllike my ownership era and it's
where, like, I'm comfortablewith myself, I am comfortable
with my skills and I'mcomfortable with where the team

(52:09):
needs to go next and I'm excitedabout it Great news I love this
era for you.
Yeah, me too, like it should bea whole Taylor Swift album all
on its own.

Sarah Caminiti (52:24):
It really should , I will listen to it if it is,
but I'm glad that you were ableto start this era talk on your
very first podcast, which isanother.
I mean this is a transition to.
I mean you're kind of inyourself and you know what
you're capable of, and I thinkthat other women especially who

(52:47):
have found themselves in asimilar career path between
burnout and leave and startingin something totally different
and being able to experiment andmove forward with staying true
to yourself the whole timethat's inspiring and I'm so
happy that you were able toshare that.

Jenn Southan (53:09):
Thanks, yeah, I think you know, as women we Jenn
are often led to believe that weshouldn't act confident and we
shouldn't I don't, I don't wantto like say the word because I
don't think it's that, I don'tthink that is what it is right.

(53:29):
But I think when you have aconfident woman, they often come
across, as you know, sometimesbrash or something like that.
So women oftentimes try to makethemselves smaller.
I was very fortunate.
My dad never raised me that way.
You know.
He always believed in and toldme I could do anything.

(53:51):
I put my mind to confidentlystep up and be like, no, like, I
know this.
It's a good place to be forsure, and hopefully someone will
hear it and it'll resonate withthem.
They ever want to chat.

(54:12):
I'm always happy to chat and besomeone's cheerleader and happy
.

Sarah Caminiti (54:18):
Yeah, well, good , I'm so happy for you, jen, and
I think that this is a journeythat will resonate with a lot of
people and people will want totalk about it, and I'm so happy
that you allowed yourself thisspace to connect with me and you
gave me your time and yourcandor and honesty, and I'm just

(54:39):
very grateful for you.
So thank you.

Jenn Southan (54:42):
Yeah, thank you, I am grateful for you as well.
I always enjoy any conversation.
I'm a Jenn of where you'rethere.
Oh, thank you, I appreciate theinvitation and, yeah, always
here.
If you want to chat more,awesome, I will definitely take
you up on that.
Definitely take you up on thatJenn

Sarah Caminiti (55:10):
I told you you never would have realized this
was her first time on a podcast.
Thank you, jen, so much fortrusting me with this special,
special episode.
Thank you, listeners, forspending time with us and being
so open to change.
Hopefully you feel inspired orempowered after listening to the

(55:30):
incredible leaders like Jenthat have gifted me with their
time on this show.
Thank you again to Buzzsprout.
Also, thank you to Elevate CXfor letting me bounce ideas off
of all of the folks in thatcommunity.
If you haven't picked up yourtickets to the event in Denver,
don't wait.
September is coming soon.
Also, if you're looking for anoption closer to you, if you're
not in the United States andyou're in Europe or you're in

(55:52):
the UK, I will be heading toLondon on November 8th for the
Elevate CX event there and Iwould love to see you.
Feel free to reach out to me orto Sarah Hatter if you have
questions about that event.
We can't wait around to seechange happen when you feel it

(56:15):
in yourself that a better wayexists.
You owe it to yourself and tothose around you to try, because
great things happen when you do.
Thank you again for spendingtime with me.
Thank you to Jen for trustingme.
Have a great day and I'll seeyou soon.
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