Building and Scaling Customer Success Teams: A Startup’s Playbook | The Pair Program Ep53

In this episode, we sit down with Romaine Buck, VP of Customer Success at Articulate, and Toni Ann Careccio, Chief Customer Officer at PortPro, to explore the evolving role of Customer Success (CS) in startups and beyond. Both Romaine and Toni bring a wealth of experience in building and scaling CS teams that drive real value for customers and businesses alike.

They discuss:

• The impact of Customer Success: How CS helps companies uncover the “why” behind customer needs
• Key differences between customer success and customer service teams, and why this newer discipline has become essential in tech
• The role that CS teams play, including managing renewals, upselling, and building strong customer relationships
• Fostering a culture of continuous learning and adaptability within CS teams
• Where Romaine and Toni see this field heading for startups and beyond

If you’re scaling a startup, leading a CS team, or just curious about how Customer Success drives business impact, this episode is packed with actionable insights and strategies.

About Romaine Buck: Romaine is the VP of Customer Success at Articulate - an e-learning software company for creating workplace training. Before Articulate, Romaine was the Director of CS at Sprout Social and led CS for the central region of LinkedIn’s Sales Solutions product. Romaine transitioned into Customer Success after a sales career at LinkedIn and Monster.com. Prior to saas, Romaine also had careers in property management and journalism.

About Toni Ann Careccio: Toni is the Chief Customer Officer and Board Member at PortPro, a technology company with deep expertise in the global drayage industry. She has built an expert team of drayage and customer success experts to ensure that PortPro’s clients are taken care of from the minute they join the company by carefully listening to their needs and addressing their concerns. Before her role at PortPro, Toni worked as an Associate at Edison Partners where she was responsible for sourcing and evaluating investment opportunities in the Enterprise Solutions sector. Prior to this she co-founded and served as Chief Operating Officer for Axle Technologies, a robust ELD and Fleet Management Solution for trucking companies in the US and Mexico.

Welcome to The Pair Program from hatchpad, the podcast that gives you

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a front row seat to candid conversations

with tech leaders from the startup world.

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I'm your host, Tim Winkler,

the creator of hatchpad.

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And I'm your other host, Mike Gruen.

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Join us each episode as we bring

together two guests to dissect topics

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at the intersection of technology,

startups, and career growth.

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Welcome back to The

Pair Program, everyone.

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Tim Winkler here with Mike Gruen.

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Mike, um, Halloween is, is right around

the corner and, uh, Google just recently

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released their top trending costumes that

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So they've got any character

from Beetlejuice, any

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character from Inside Out 2.

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Ray Gunn, the Australian break

dancer from the Olympics with

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the green and yellow tracksuit.

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That seems legit.

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Pop star Sabrina Carpenter, uh,

who I'm sure you and I, I don't,

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I have no idea who that is.

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Um, and then Wolverine and

Deadpool for a duo costume.

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So of those options, you

know, what are you going with?

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Beetlejuice

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Mike Gruen: all day.

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There's so little doubt.

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And see, I mean, yeah, Beetlejuice.

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Yeah.

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Have you seen the movie?

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Not the I saw the original one.

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Yeah, I saw the original.

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I haven't seen the new one.

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Tim Winkler: Oh, OK.

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Well, the new one's

supposed to be pretty good.

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I'm sure I was hoping you were going

to go with the the duo costume.

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You'll be Wolverine.

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I'll be Deadpool.

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Oh, yeah.

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Missed opportunity.

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I just a little collab.

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Yeah.

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Now I'd totally be down next.

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I think we both have to dress up

because I think we'll have one

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right, right around Halloween.

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Sounds good.

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Um, what about you ladies?

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What are you going with any, any,

any of those that jump out to you?

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Romaine Buck: That was quality for sure.

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I would also do, I think

something Beetlejuice related.

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And I did see the second movie as well.

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And it is Hilarious.

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It is so good.

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There are a couple scenes in there

that I was just laughing out loud.

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So unexpected kind of fun.

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I'm going to see,

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Tim Winkler: I'm always

just annoyed by critics.

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Like everybody just wants to

give bad reviews these days.

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I feel like, and so like everybody bashes

it, but you know, Tim Burton's a genius

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and you kind of know what you're getting

with anything he puts out, you know?

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So I

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Toni Ann Careccio: mean, I'm a review snob

and I think talking to two CS people here,

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I think we're both very much into reviews.

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Tim Winkler: I'm a big review person,

but I, I just know that like, there's

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a lot of negative, like the more, the

more reviews that are usually going

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to be negative are going to be the

ones that people want to check out.

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Well, that's because that's what

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Mike Gruen: people click on.

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So that's the problem.

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Yeah.

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That gets reversed against clicks.

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And that's, that's,

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Romaine Buck: it seems like all the

people that are doing reviews now

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are people you've never heard of from

a publication you've never heard of

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from a thing you've never heard of.

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Right.

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Is it some dude in his basement?

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Just two dudes on some podcast somewhere.

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Tim Winkler: Yeah.

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I actually think it's just a bot.

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I don't even think it's a real person.

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It's just a bot out there.

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Yeah, just stirring something up.

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Alright, well, we'll have a follow up

episode about reviews here at some point.

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But let's give the listeners a little Q&

A on what today's episode is all about.

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Today we're going to be talking all about

customer success teams, um, specifically

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building and scaling customer success

teams and kind of growing startup

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environments and how that might differ

from larger organizations as well.

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Uh, so in true program fashion, we, we

do have two excellent guests joining

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us to approach the conversation

from a few different perspectives.

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Our first game, uh, first guest, Romaine

Buck has experienced transforming

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customer service teams into.

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Customer success teams at companies

like Articulate and LinkedIn.

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She's currently the vice president

of customer success at Articulate, a

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workplace training software company

that provides online training courses.

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And we have Tony Pizzano, a

repeat kind of startup founder

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and currently the chief customer

officer at PortPro, a startup that's

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building a transportation management

software for the trucking industry.

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Uh, important to note that Tony built

out Port Pro's customer support and

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customer success teams, which I'm sure

we'll expand on in our discussion.

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So Romain and Tony, thank you both

for joining us on the pair program.

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Romaine Buck: Thanks

so much for having us.

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Awesome.

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Tim Winkler: All right.

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Now, before we dive in, uh,

we do, uh, kick things off

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with our pair me up segment.

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So here's where we'll all go

around the room and spit ball a

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complimentary pairing of your choice.

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Mike, you kind of lead us off what,

uh, what your Pairing for today.

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Yeah.

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So mine's

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Mike Gruen: a little on the weaker side.

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Uh, but over the weekend, you

got to set the expectations

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low, uh, over the weekend.

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Uh, I, my son and I were down in DC,

uh, looking at, uh, colleges and on

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the tour on the college tour, I was

reminded of how much free stuff is in DC.

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So that's my pairing is the

DC, this DC and free stuff.

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You have access to all these museums.

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Um, the Smithsonian

and so on and so forth.

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There's all of these great things in DC

and resources, um, that really put it like

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as a top notch city from that perspective.

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And you sort of think about New York city.

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It's like, you know, you want to go

to a museum that's going to, you know,

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you have to give a pretty big donation.

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So, um, DC and, and, and free

stuff, um, DC free stuff.

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Tim Winkler: Sometimes it

doesn't feel like that.

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No, definitely not.

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Mike Gruen: And not all museums are free.

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Uh, but yeah, true.

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But the Smithsonian

does, but there you go,

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Tim Winkler: I will say I'm a huge fan of

the fact like a lot of those museums are

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free because it just encourages you to

go and kind of learn something new and,

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um, something I kind of slack on when

I get, get my family, my daughter out

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there a little bit, uh, she's a little

young, but when, when she gets a little

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bit older out there to To experience it.

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And you're right, save some, save

some money, uh, while you're doing it.

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Yep.

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But you'll probably pay

for it in parking though.

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No, well, no, you, I mean,

you take the, take the,

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Romaine Buck: take the train.

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We're all paying for it in

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Mike Gruen: taxes, so it's just pay

for it in your tax dollars at work.

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So you might as well take advantage of it.

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Okay.

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All right.

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Do DC and free stuff.

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There you go.

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Tim Winkler: Um, I'm gonna

queue up my . Hold on here.

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Oh, there's props.

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I love it.

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Got a prop leaning.

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I got prop for this one.

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Alright.

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Um, I'm gonna go with this is.

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Kind of difficult now.

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Um, I'm going to go with

island life and pirate parties.

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So my family and I, we've been

living the last month on a small

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island off the coast of Georgia.

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It's called Tybee Island.

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And, you know, it's for us, you

know, we're not just vacation.

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We're working, we're living in a, in

a, in a different destination, but, uh,

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you know, fortunate to be able to do so.

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But, yeah.

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Very different environment than

the high speed lifestyle from

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back home in Northern Virginia.

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And so we, uh, every, every year,

apparently this, this island,

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they host something, uh, in

October called pirate festival.

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And I'll just say that this entire

island goes all in for this pirate fest.

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And it's pretty amazing to

see, but they've got a parade.

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They've got, uh, something called

the Buccaneers ball that they

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kick off with from like Thursday

to Sunday where they name like a

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pirate King and a pirate queen.

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And everyone's dressed head to

toe and like legit pirate garb.

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So of course we had to wrangle

together like costumes and participate.

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And, uh, it was just a really

interesting, amazing time.

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Uh, to the point where I think we're

going to try to make it an annual

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tradition and come back out here.

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Toni Ann Careccio: Uh,

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Tim Winkler: you know what, I, there's

so many things on the agenda that we

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only kind of made it to a few things.

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A treasure hunt sounds.

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Pretty obvious.

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I know there's a lot of bar crawls.

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It's a big drinking,

uh, island, apparently.

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And I think, you know, that's

kind of the pirate way is,

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Romaine: uh,

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Tim Winkler: you know, roll

around, you know, uh, it's kind of

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open, open container policy too.

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So everybody's just

kind of bouncing around.

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Um, but yeah, that's, that's

going to be it for me.

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I'm going to go with the

island life and pirate parties.

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And I recommend anybody, Check

out, uh, Tybee Island if you're out

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here for third weekend in October.

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Romaine Buck: I love that.

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If, if you're pirate people, you

have to try out Disney Cruises

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because they have Pirate Night every

time you go on a Disney Cruise.

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And every, same thing,

everyone is in full garb.

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Oh, that's fun.

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And they have like all

kinds of fun activities.

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It's a good time.

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And if, and I did my first

Disney Cruise two years ago and

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it was, Around Halloween time.

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So that's awesome.

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Dooms everywhere, which was fantastic.

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Not only were all the characters

in costume, but all of the

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adults and the little people.

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And it was a ton of fun.

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And I don't even have kids.

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And I was

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Tim Winkler: just going to ask.

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That's so fun.

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Did they tell you in advance?

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So like, you know, to go and

get your pirate garb in advance?

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Romaine Buck: Yes.

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They tell you in advance.

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Okay.

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That's, that's cool.

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There's all always pirate night.

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And then if you're a slacker like me, you

can also, they pass out like bandanas.

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So at the very least you have a bandana

nice to hook you up for for pirate night.

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Yeah.

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Tim Winkler: All right.

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Well, I'll have to remember that.

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'cause, uh, now that we have a a,

a young child, it'll, you know, we

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can, we can go on the Disney cruise.

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Well, you said you went,

you went out there as well.

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I mean, I imagine it's just,

uh, pretty much parties for

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adults, kids, everything, huh?

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Romaine Buck: Absolutely.

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And what I also really loved about

it is they have areas for kids.

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So you can take your kids

to like the kiddie daycare,

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depending on what age they are.

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And then you, there were so many

adults that I met who were like,

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I don't know where my kids are.

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They're at the imagineering thing.

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I haven't seen them since.

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Yeah.

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And the parents were,

you know, having a blast.

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So it's a good time and you

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Tim Winkler: don't have to drive home

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Romaine Buck: and you don't

have to do anything you

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Tim Winkler: Awesome.

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All right.

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Some good recs for the listeners.

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Um, let's pass it over to our guests,

uh, for their intros and pairings.

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Um, Romain, maybe just a quick

intro from you and your pairing.

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Romaine Buck: Yeah.

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I'm Romain Buck.

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I'm the vice president of customer

success here at Articulate.

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I've been here about four years

and prior to Articulate, I was

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the director of customer success.

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at sprout social, which was a social

media management, um, software company.

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And prior to that, I was at LinkedIn,

uh, and spent seven years there.

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And that's really where I moved

into customer success from sales.

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So I'd been in sales

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And then there came that point

in time where I was like, Hmm,

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what else do I want to do here?

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And I realized that the thing that

I loved most about selling was.

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Helping customers have that aha moment

and make those connections and helping

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them be successful, which became

customer success and haven't looked back.

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It's been fantastic.

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And I would say my pairing,

which is fresh from a week out

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in the Western part of the state.

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And I live in South Dakota now it would

be road trips and good tunes because

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driving five and a half hours through.

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The planes that are South Dakota.

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You need good music to keep you going.

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So I would say it'll make or

break your road trip for sure.

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Tim Winkler: Uh, it's spot on.

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Yeah, we did a road trip cross country

and we, we, uh, went from Chicago to South

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Dakota and that's a long, A long road of

nothing, uh, a lot of, uh, like solar, you

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know, uh, wind turbine farms and whatnot.

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Uh, what's, what's your playlist,

what, what kind of music are you

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jamming out to on the road trip?

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Romaine Buck: Anything

that you can sing along to.

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So that goes from pop music to

nineties hip hop to just good

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old fashioned, like, yeah.

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80s tunes as well.

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I love it.

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And I know that road trip from Chicago to

South Dakota because I made it many times.

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I moved here from South Dakota,

from Chicago about five years ago.

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Four years ago now and, um,

was building a house here.

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So I was driving back and forth and

that is eight hours of not good times.

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A lot of music.

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Yeah.

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Windows

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Tim Winkler: down, music,

stay, staying awake.

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I mean, that's, that's pretty key.

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Romaine Buck: Awesome.

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Tim Winkler: I dig it.

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That's a great pairing.

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Um, uh, Tony, how about yourself?

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Quick intro and your pairing.

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Toni Ann Careccio: Yeah, so, um, I'm Tony.

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I am the chief customer officer

at Port Pro, which is an operating

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system for the dry age industry.

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Drayage just means the type of

trucking where you're transporting

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containers in and out of the ports

and the rail, the rail yards.

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Um, I lead our customer success team.

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I also lead our marketing.

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And I have a pretty, I would

say, nonlinear career path.

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I grew up with a family business

in trucking, but, you know, went

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to college as a dance major.

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And then I worked on Wall Street

for 4 years on a trading desk.

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And then after that, I started my

1st, um, I co founded my 1st tech

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company called Axel, which was

a software company in trucking.

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And then I, after that company was

acquired, I joined a venture capital

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firm where I was investing in supply

chain and logistics tech companies.

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And then I kind of rekindled with

my cousin who is the co founder of

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Axel with me and we started PortPro.

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And, um, yeah, I've done everything in

the company from leading our sales team

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to, Oh, wow, we have a lot of sales.

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How do we implement the software, right?

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To kind of overseeing our

onboarding and then our support.

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And now I'm really happy to be in

customer success and marketing.

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I would say for my pairing.

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I am really into mindset and wellness.

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And so one of my favorite

activities is hot yoga.

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So I'm pairing like

saunas with, with yoga.

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And it's one of my, one

of my favorite activities.

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Tim Winkler: Intense.

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One of the most intense, intense

workouts I've ever done was, I

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felt like I was dying, honestly.

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Yeah.

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I'm not a yoga.

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Romaine: I do not want to.

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I'm

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Tim Winkler: just kidding.

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Toni Ann Careccio: Yeah, basically.

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Yeah.

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Tim Winkler: But, you know, you, you,

you walk away from it and you feel

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Toni Ann Careccio: like a million, a

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Tim Winkler: million bucks.

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Yeah.

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Toni Ann Careccio: Yeah.

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Tim Winkler: Yeah.

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Um.

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That's great.

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I like the pairing and,

uh, your background.

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I'm really, I'm really excited to bring to

the conversation because you've, yeah, you

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mentioned it's such a diverse background.

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So you're, you're approaching

customer success from, you know,

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looking through multiple different

lenses, which is going to be a

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great addition to the conversation.

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And so I want to make the most of

our time and, um, uh, jump into it.

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So.

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Thank you.

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Uh, let's, let's, let's transition at the

heart of the discussion at this point.

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So like I mentioned, we're, we're

talking all about customer success

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teams in today's episode, and so we're

going to have each of our guests, I

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mean, they already kind of gave us a

little bit of a brief overview on, you

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know, their introduction into customer

success, but expand a little bit on

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that, um, we'll define, you know, what.

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They think customer success is and

how it differs from customer service.

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Uh, we'll explore like, when is

that right time to start building

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out a customer success team?

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Uh, how to kind of structure

and scale these teams.

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And we'll close with some thoughts

about the future of the space as well.

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So, um, Romain, let's,

let's start with you.

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You kind of gave our listeners a little

bit of a back backstory on, on your

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journey into, to customer success.

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You know, you can expand on that a little

bit more or, or just jump right into,

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you know, how you define customer success

and, you know, how that definition has

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evolved over, you know, the, your tenure

in different roles throughout your career.

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Romaine Buck: Yeah, I think it's super

interesting because customer success is

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still pretty new as, uh, A job, if you

will, when I was at LinkedIn, actually,

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um, and I took my first customer success

job, the job was called, um, solutions,

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product consultants, uh, and that was

because our director at the time didn't

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feel like we had all of the right

elements yet to call it customer success.

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And as we evolved our business

and the way we were interacting

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with customers, we kind of.

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earned the title of customer success.

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And for me, customer success

is really thinking about how to

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obviously, um, gain maximum R.

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O.

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I.

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Because that's what we always want to do.

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That's why we're here while helping

your customers reach their goals.

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And goals.

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So in order to do that, we

have to know why did they

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come to us in the first place?

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Why did they buy and articulate?

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We are a an E learning software platform.

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And 1 of the things that I talked

to my teams about all the time

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is it's overly simplistic to say

people come to articulate because

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they want to create E learning.

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Sure, they do.

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But the question is why when we understand

the why behind what's motivating

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our customers to come to us, then we

know how they're going to measure us.

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And then we know how to

help them be successful.

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And until you understand what a

customer wants to truly accomplish,

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uh, you're not going to be able

to help them be successful.

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And I love the equation that Tony,

you've probably seen this from Gainsight.

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It's CS equals CX plus CO.

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Customer success equals customer

experience plus customer outcomes.

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And that CX part, that customer

experience, that every person within an

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organization, not just the CS team is

responsible for the customer experience,

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whether it is marketing or the sales

team or the product team or the finance

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team and the support team, everybody

that your customer interacts with.

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As a hand in that customer experience,

and then you pair that with what

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are they trying to get out of this?

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What's the outcome when

you get those things right?

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Then you help your

customers be successful.

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And that is I will live and die by that.

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And I think it's super important.

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I'm very different than

customer service, which is.

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Something's gone wrong.

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Let me help you fix it.

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It's super transactional and super

reactive and something's already

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gone wrong when they're coming

to the customer service team.

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Um, customer success should be proactive.

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We should be understanding what our

customers are trying to accomplish

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and helping them get there.

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We shouldn't be waiting until something's

broken before we're reaching out

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and connecting with our customers.

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And so that's how I kind of

keep those two things different.

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Tim Winkler: I just think it's so

fascinating how it's like a fairly new

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ish department and, and, uh, you know,

kind of role or, or team, um, just for

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context for, for our listeners, cause

I want to, you know, kind of make some

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comparisons to, with Tony's, um, you know,

kind of company size and everything else

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articulate from a headcount perspective,

can you just kind of give us an idea of

417

what, where you all sit and then what's

the size of the customer success team?

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Romaine Buck: Yeah, so articulate.

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We've got just under 500 employees

right now, and we are fully remote.

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Always have been always will be.

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We've never had an office.

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So that makes it a little bit

of a unique culture as well.

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And the CS team.

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So I started 4 years ago here.

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We had 10 people on the CS team.

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And now at the end of this

year, we'll have almost 40.

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So we've really been able to grow

and scale and do some amazing things.

428

And really, part of my

journey is helping people.

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Transition this team from what

was truly 100 percent reactive to

430

being more proactive and being more

of a trusted customer advisor and

431

consultant for our customers and

getting out of that vendor box.

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Tim Winkler: Yeah, that's great.

433

Somebody once told me like a sales

hack that if you're looking to identify

434

like prospects, some really successful

companies, look for companies that

435

are hiring customer success folks

right now, because usually they're

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scaling their customers as well.

437

So it's a, uh, it's a good, a good

area to be in, you know, you're, you're

438

obviously front and center and working

closely with, with the customer.

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And, and like you mentioned,

maximizing that ROI.

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So I think it's a really, really

great, uh, you know, department, uh,

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to, to be a part of a growing company.

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Uh, Tony, let's, let's kick it to

you real quick and, you know, maybe a

443

little bit more on, on how you approach

customer success and how you, how

444

you see it and how you're, how you're

building out those teams at Port Pro.

445

Toni Ann Careccio: Yeah.

446

So just for perspective, we are about 150

employees globally, I would say about.

447

80 to 90 of those people are based

in the US and then the others we have

448

offshore offices and so 150 employees

and about 8 of those folks right

449

now are include the CS department.

450

So, to remain point, I think it's really

interesting that the term customer success

451

really just kind of became a thing.

452

Over the last, I don't know, 5 or

so years, it's really just become

453

such an important part of companies,

specifically technology companies.

454

I think, um, you know, when you look

at a lot of the studies, it shows that

455

acquiring a new customer can cost.

456

5 to 7 times more than retaining an old 1.

457

I think that, of course, depends on the

industry you work in, but it really just.

458

Makes you realize how important.

459

Retaining your customers are and so

that's my job at 4 pro is making sure,

460

um, You know, our customers are happy

that they are utilizing our system

461

and the different features within

our system, but not only utilizing

462

the features using them correctly.

463

So, making sure that they're,

um, optimizing their operations

464

with the tools that we provide.

465

Um, our team is really

involved in making sure that.

466

Our customers are, um.

467

Like I said, happy, but,

um, achieving their goals.

468

So one thing that we do really

often when we're onboarding a

469

new client is we are asking them,

hey, why did you sign up with us?

470

Right?

471

What are your goals as a company?

472

And throughout the implementation

process, the goal is really just to

473

get their system stood up, but then

it becomes the responsibility of the

474

customer success team to make sure that

we're helping them achieve those goals.

475

Thanks.

476

And measure those goals.

477

So, on every, you know, call or

quarterly business review we have

478

with our customers, we're looking at

those initial goals that they set and

479

helping them, you know, kind of evaluate

where they are since implementing our

480

software and what more needs to be

done to help them achieve those goals.

481

Um, we are really big

in product led growth.

482

The good thing, um, the cool and like

differentiating thing about us is

483

that, you know, our founding team comes

from the dry edge trucking industry.

484

So, we had a lot of experience and

expertise on what was initially going

485

to be built to help the companies.

486

Achieve their goals.

487

Um, however, as we get bigger and

bigger, it's really important that

488

we're taking our customer feedback

and then ultimately looping that

489

feedback into, you know, feature

development in our in our products.

490

And then the last thing I'll say,

Romain, you, you touched on it, but for

491

me, this might, this might be a good

segue into the next question versus

492

customer support, but customer success

is really about being, being proactive.

493

Mike Gruen: So I think the point

you touched on both of you about

494

the why is so important because,

so I think back to, I was at a

495

cybersecurity training platform company.

496

We were.

497

We had a customer success team.

498

I worked very close with them to

sort of support them and on board.

499

And we were building all these data

models to try and predict churn.

500

And one of the things that was very

interesting was that usage of the

501

product by the admins sometimes meant.

502

That they would churn and sometimes meant

that they didn't, and it was really got

503

back to the, like, why are you here?

504

Like this idea of like, oh, I

want to set it and forget it.

505

If I never have to log into this

thing, then it's working for me versus

506

other people that were like, no, I

want to be in there every day and

507

twiddling with it and playing with it.

508

And so knowing that you can't just

look at the data and look at, like,

509

are these features being used?

510

And know whether or not that's

going to be like a predictive thing.

511

I think that

512

Romaine Buck: is so

513

Mike Gruen: true.

514

Romaine Buck: That is so true.

515

Yeah.

516

Everybody's health score tells

them something different and

517

you have to understand what good

looks like for your customers.

518

And sometimes that varies by industry.

519

So when I was at LinkedIn and we were

selling, um, sales navigator as the

520

product there, and We had a health score.

521

We like to see 80 or above to indicate

that our customers were healthy, but

522

we noticed that all of our finance

customers were like in the 30s.

523

So they always were in the

red, looked horribly unhealthy.

524

And what we came to learn was

when we talked to those customers,

525

they'd say, no, it's great.

526

This is exactly what I

thought it was going to do.

527

Their uses was just always

going to be lower because of.

528

Their industry, whereas other

customers would be pushing 100.

529

So it really is understanding what

matters to your customer and then

530

measuring accordingly and never going

in thinking, well, this looks terrible.

531

Oh my gosh, you're going to churn.

532

Um, because.

533

Sometimes they're totally happy with that.

534

And

535

Mike Gruen: right, which

536

Romaine Buck: is,

537

Mike Gruen: which is funny because

I had a different experience

538

where I was the customer.

539

I remember talking to my customer

success person every, every quarter.

540

And she's like, yeah, I, you guys,

you're at the top of the list.

541

Like in terms of guys look great.

542

You're getting lots of usage.

543

And I'm like, yeah, just a reminder.

544

Uh, we're not renewing the contract.

545

Like it was like, we look

so healthy, but at the end,

546

it's just, and she's like,

I know, I know what you guys

547

are helping my numbers, right?

548

Toni Ann Careccio: That's why relationship

building is like one of the most important

549

parts of a customer success function.

550

Right.

551

Because.

552

You know, if your customer is not happy,

they're going to come to you and talk

553

to you because you've spent that time

building the relationship with them.

554

And it's really the

sentiment right that I think.

555

Is more important than just

system system usage and I think.

556

Without that relationship, you don't know

what the sentiment of the customer is.

557

Mike Gruen: And I think

that's an important thing.

558

I want to ask you guys how you build

trust because so at one, I've worked

559

at several different companies with

different customer success and one

560

company I worked at that we iterated that

our head of sales churned a little bit.

561

So there was a lot of iterations of

what customer success looked like.

562

And one of the challenges that one,

one iteration had was they had a lot of

563

quotas, they had a lot of expectation

of sales and expansions, not just.

564

Not just retention, which makes sense,

but really about expanding and and

565

it's sort of in talking to some of the

people, it sounded like it put them a

566

little bit of a conflict of interest in

terms of like, how do I gain someone's

567

trust when they know I'm just trying to

like when they think I'm just trying to

568

sell them on buying more or expanding?

569

I'm curious how you guys sort of tackle

that or what your thoughts are on that.

570

Um, do you even see that as a, as an

important part of customer success?

571

Is that sort of expanding the,

the just throwing it out there?

572

I think

573

Romaine Buck: that's such a

great question and I do see that.

574

And my team at articulate is a little

different because when I started, the

575

team not only had a retention number,

but it also had an expansion number.

576

And then as the sales team

evolved, we moved that expansion

577

number over to the sales team.

578

So now the sales team is

responsible for selling.

579

More product than we just

launched AI at articulate.

580

And so they're responsible

for selling that.

581

We're going to be launching localization

pretty soon, and they're going to

582

be responsible for selling that.

583

But if there's a partnership between

success and sales that I think sometimes

584

gets lost, sometimes gets a bad rap,

but it's also always critical because

585

you need to understand what your swim

lane is and who is building the trust.

586

Because the success team sometimes,

my success team sometimes struggles

587

with this idea of I'm not supposed

to be selling to my customer.

588

I'm supposed to be just

making sure they're happy.

589

And I'm the one that says,

wait, we're in success.

590

We are selling, we're

selling every renewal.

591

And so it's always important for us to

make sure that The relationship you have,

592

you are continuing to develop so that

that sale, that renewal is a no brainer.

593

And it's obvious and that we're uncovering

opportunities for expansion so that

594

we can intro our sales counterpart

and that they can upsell really

595

easily because the customer needs

the thing that we're talking about.

596

So it's not a smarmy kind of Sales motion.

597

And that's the fear.

598

I think that some folks have and

a lot of customer success people,

599

myself included, came from sales

and didn't want to do that anymore.

600

And so sometimes people have a fear

that they're going back into sales

601

when they're in customer success.

602

Um, and every organization is different.

603

I've been at other organizations where

CS teams didn't have a quota at all.

604

And it was really just about

health and customer retention.

605

And I've been at other

organizations where.

606

Their 100 percent was a number.

607

Uh, and so I think how you build

your team determines what those

608

swim lanes are and how you build

that trust to support that motion.

609

Toni Ann Careccio: This topic for

me, no, I was going to say this topic

610

for me is just so relevant right

now because, um, we just introduced.

611

Our CS team actually owning upsells,

so they've always owned renewals.

612

And they've owned expansions, which in our

definition is like, we charge based on the

613

number of drivers a trucking company has.

614

So, if they go from 10

drivers to 20 drivers.

615

We expand the contract size.

616

But there's really not a

lot of sales motion there.

617

It's like, you've just

increased the number of drivers.

618

So we're going to expand your contract.

619

We just introduced the idea of upselling

into different product lines and features.

620

And at first the CS team

was very hesitant about it.

621

They had this like anxiety around

sales and we really had to.

622

Um, coach them, like, don't freak out

over the quota or the number, right?

623

You have to more so look at this as an

opportunity to help your customer, right?

624

You have the relationship

with your customer.

625

You know what products

and features are using.

626

You know what they're not using.

627

You know what their goals are.

628

And so, and you know what our

product offering is, right?

629

So if they're not using certain

features, but those features

630

are going to help them better.

631

Um, you know, optimize certain areas

of their operations, which will

632

ultimately help them achieve their goals.

633

It's like view it from more that lens

than like, this is sales and I have to

634

hit this quota, you know what I mean?

635

So it's something like,

636

Tim Winkler: you know, you have an

ability to solve more of the customer's

637

problems versus the one kind of

problem that you were looking at.

638

Do you think that breakdown,

639

Mike Gruen: um, is a function of

size because that going iterations,

640

like the one, the team that I'm

thinking about was smaller, they.

641

It was the customer success

people that were very much

642

involved in those expansions.

643

But the product offering was

still something that they could

644

sort of keep in their head.

645

They didn't have to go.

646

And then as we got bigger, and

as we had more to offer, and as

647

there was, they had more customers

that they're trying to help.

648

It went, it then switched more

to what Romain was talking about,

649

where we, they were, they were in.

650

Account executives to come in and

really help on the expansions because

651

they were the product experts.

652

And there was a lot of conversations

that would happen before that.

653

You know, obviously, Hey,

this is the customer.

654

This is what they use.

655

This is what they don't use.

656

But I wonder if, is it, is there

something about the function

657

of the size of the company or

658

Toni Ann Careccio: It could be.

659

What I know is that we've done.

660

We, we, we test a lot of things, right?

661

Like we do something.

662

If it's working, we, we change

and we see how that goes.

663

And if that doesn't work, we change.

664

We see how that goes, right?

665

We try to move really fast in that regard.

666

Um, and so for a while, our sales team

and AEs owned the upsell process and.

667

I don't know.

668

I think that had its own limitations.

669

1.

670

I think that was super distracting

from the new business quotas that

671

the sales team had to have to hit.

672

Um, so I think it was distracting in that

regards to, um, like I said, the CS team.

673

I really try to make sure our success

team is building strong, meaningful

674

relationships with the customers and

really understand their goals and usage.

675

So it's like what better person to

upsell something than the person

676

that has a relationship, right?

677

And knows where the company stands as

opposed to the sales team, just trying

678

to hit this quota, randomly calling

a customer of ours when they really

679

don't know the usage or the sentiment

of the account to try to upsell them.

680

It just didn't sit right with me.

681

So we decided to make this

switch, um, fairly recently.

682

And so we'll see in the next, you

know, three months, this, this

683

quarter, how, how it actually

goes, but I'm excited about it.

684

Tim Winkler: It kind of leads me to it.

685

You know, the next, next question

I wanted to ask you all, because we

686

have a lot of founders that are, you

know, listeners that are probably in

687

the very early stages and wondering

when is that right time, right?

688

Because at the.

689

The early stages, right?

690

The founders are usually the one that are

doing most of the customer relationship.

691

Um, when, when did you see that as

the need to start scaling a team

692

telling maybe you're, you're, you're

a good one for this because you

693

know, you've been with port pro from.

694

Early on, um, you know, is there a

number that you kind of figured out

695

was like a ballpark 20, 30 customers?

696

How do you determine, uh,

when is that right time?

697

And then how, how do you determine

when is too much on one person's

698

plate to, to justify expanding?

699

This

700

Toni Ann Careccio: is a great,

this is a great question.

701

I would say, It wasn't until we hit around

702

4 million, 3.

703

5 to 4 million in ARR where we

started actually like building

704

out our customer success team.

705

Um, and then that's just scaled based

on, you know, capacity, how many

706

clients can I successfully manage,

um, without being too overwhelmed.

707

And it's like, okay, I'm too overwhelmed.

708

Okay.

709

Let's look at hiring another

customer success manager.

710

And it's kind of just grown organically.

711

But up until that point, it's been the

account manager leading the onboarding

712

and our customer support team really

managing, um, more of like the, the day to

713

day sort of questions from the customer.

714

But I would say it was

around the 3 and a half.

715

Million error mark, where we started.

716

Building out our customer success team.

717

Tim Winkler: That's fascinating.

718

Um, uh, Romaine for you, you know,

you've, you've been scaling the customer

719

success teams that articulate, you

said from 10 to, what do you say?

720

40 now or almost

721

Romaine Buck: 40.

722

Yeah.

723

Tim Winkler: So then, you know, how did

you approach it for maybe, you know,

724

this is more of like maybe looking

at mid to later stage startup growth,

725

you know, where, where did you come

in and why did they bring you in?

726

Did you come in as a VP or

did you grow into that role?

727

Romaine Buck: Yeah, I did come in as a V.

728

P.

729

And what was interesting was the customer

success team was reporting in to the V.

730

P.

731

Of marketing when I arrived.

732

And so customer success

was 100 percent reactive.

733

All of the interactions were

basically going through marketo.

734

And so there was this outbound motion

through marketo and then the C.

735

S.

736

M.

737

S.

738

Would respond to customers

through a Salesforce case queue.

739

And that's what I walked into, um, four

years ago and was like, okay, um, so

740

we're going to try some different things.

741

And it's been an interesting

journey because one, it was.

742

Uh, really getting the team to shift

and think change their perspective about

743

what customer success looks like, but

also getting the organization to think

744

about customer success differently too.

745

So being the first dedicated customer

success leader at articulate and

746

having the experience of coming from

some great organizations, I was able

747

to come in and think differently.

748

Uh, and we built segments

to define segments.

749

And so, whereas There were 10 people

who would just pull cases out of a case

750

queue and support whatever they wanted.

751

So one day a CSM is working on Microsoft

and the next day they're working

752

on Joe's body shop sort of thing.

753

And it was just because that's

what they pulled out of the queue.

754

So we created distinct books of business.

755

Every CSM had an assigned book.

756

We had a SMB, a mid market and

enterprise segment, and just really

757

kind of Started putting those

foundational elements in place on.

758

We've still been working through that.

759

I built also the customer success

enablement function as well as

760

brought in customer success operations

because these were gaps for the team.

761

The team was doing their job, but

there were skills that were missing.

762

And so it was really clear that there

was an opportunity to help the CSMs.

763

Be better.

764

C.

765

S.

766

M.

767

S.

768

And so that's where the

enablement function came to play.

769

And then operations as well.

770

Of course, every organization has a

sales ops function and sales ops was kind

771

of taking care of the customer success

team, but it's a very different ones.

772

And so it became really clear that we

needed someone whose focus was how to you.

773

Build and optimize processes for

our customer success organization.

774

How can we run that?

775

And so bringing those individuals

in as well to help us really start

776

scaling, uh, and really fine tuning

some of the great work that was already

777

happening to get us to this place.

778

And I keep telling the

team was what got us here.

779

Won't get us there.

780

I've been saying that for four

years because we're still going.

781

Um, But this idea that we have to

be agile and we have to be open to

782

learning and growing, uh, because

we don't have all the answers.

783

And Tony, I love that idea of

working really fast and iterating.

784

And so really trying to get

the team to understand change

785

is just part of the deal.

786

And as you are trying something

new, it might not work.

787

And so we're going to try something else.

788

We're not going to drag the dead weight

and keep going in the wrong direction.

789

Let's cut bait and let's go.

790

And getting folks Comfortable

with that, with that.

791

Discomfort has been a big part

of scaling this team as well.

792

So we are doing something

that we've never done before.

793

We're going to build a team in Chile,

uh, and they are going to take the

794

very long tail of our business.

795

So everything kind of sub eight K is

going to move to that team and that's.

796

What we're going to stand up by the end of

the year, that will take the team to 40.

797

So we're going to take all of

that long tail business, move

798

it over to this team in Chile.

799

We'll be partnering with some of our

sales counterparts that are here, and

800

then that will free up our mid market

segment and our enterprise segment

801

and the rest of our, uh, Larger SMB

segment to really have more of those

802

strategic customer conversations that

we want them to have is right now.

803

Bandwidth is a challenge and I'm sure

bandwidth is a challenge for everybody.

804

Uh, and so making sure that we give

them enough time to do the things

805

we want them to do is also part of.

806

We're from scaling this

organization as well.

807

Toni Ann Careccio: Yeah.

808

Outta curiosity, because you

mentioned segmenting by, um, you

809

know, SMBs, mid-market, enterprise.

810

Have you ever segmented by geography?

811

Romaine Buck: No, I've never done that.

812

Um, personally at, uh, when I was two

jobs ago at LinkedIn, we were segmented

813

by geo, but we were also segmented

by revenue and some other things.

814

So we were in the central

region, which was.

815

Minnesota all the way down to Texas.

816

And then there was east

and then there was west.

817

So everybody in the office was working

the same region, but then there were

818

other, there about 14 other data

points that we were looking at with

819

our customers to determine what.

820

Segment what team they went into as well.

821

So we're not as sophisticated and

articulate with our segmenting right now.

822

So it's really just a revenue base.

823

Um, but we're looking at ways to

get a little bit tighter because

824

there's a little bit of a misalignment

between our CS segmentation

825

and our sales segmentation.

826

And we really want to get more tightly

aligned so that we can make sure that the

827

teams are partnering even better together.

828

Tim Winkler: That's why I love, I

love, uh, the two perspectives, cause

829

I feel like, you know, there's some

ideation happening here, but also

830

like hearing how, you know, Tony,

you approach it from the early stages

831

to growth stage with your own man.

832

I think it's just a fascinating,

uh, kind of continuation of, of how

833

the role and the department evolves.

834

And I think this is just on cue with

startup world in general, right?

835

Is that.

836

You, you might've come in at a

certain stage where you're excellent.

837

You're perfect for it.

838

We see this a lot in product roles.

839

And then you go through a big growth

spurt and you hit, I mean, a big round

840

of funding, you start adding on features.

841

And maybe you aren't that, that, that,

that good PM that you, you were in that

842

earlier stage, you know, it's, it's

always, uh, something that you have

843

to, you know, adapt to, but also kind

of be open and humble, like admitting

844

that maybe you aren't the best person

for this new, you know, kind of growth

845

of the company, um, might not be as

relevant for, for CS, but we see it a

846

lot of other departments, um, I want to

847

Toni Ann Careccio: say that's

this like rich verse King theory.

848

And I think everyone

in the company, right.

849

Whether you're a CSM, whether you're

the CEO has to have that mindset where.

850

It's like, okay, just because I'm the

CEO right now, does it mean I'm the right

851

fit to be the CEO when we are doing X

amount of million dollars or more in ARR?

852

Right.

853

And I think it's important for.

854

Everyone to really have that mindset.

855

Mike Gruen: I think it's funny how

many, so just across departments,

856

mindsets, that mindset, the one of

constant change, the iteration is the

857

same in product and engineering, right?

858

Like we're constantly going to be

doing new things and you have to

859

be comfortable with that change.

860

And I still remember all the conversations

with especially more junior people

861

where they'd be like, Oh, I felt

like I just totally wasted my time.

862

It's like, no, like, Yeah, we didn't.

863

Maybe that feature didn't hit right or

whatever, but it wasn't a waste of time.

864

It would only be a waste of time.

865

If we didn't learn anything, then

it would have been a waste of time.

866

And so I think it's, it's interesting

to hear you say almost the exact same

867

things that you're dealing with with

your departments in terms of that growth

868

mindset and that constant change and

be comfortable with the discomfort.

869

Exact same things I'm saying to

engineers and product people.

870

So, um, That's startup life.

871

It's

872

Romaine Buck: startup life.

873

It's so true.

874

When some people get really comfortable

in their space that they forget that

875

we are working really hard and really

fast because we're in startup mode.

876

Articulate it's been around over 20

years, but I tell people it's like,

877

we're the, we're in startup mode

right now because the way that we

878

think about the company has completely

shifted in the last six years and

879

so it was a perpetual product for.

880

a good 15 years of that time and it's

really been the last five, six years

881

that we've been selling software.

882

So this is where all of that change

has been coming and people who've

883

been here since the beginning, not

everybody loved that direction.

884

And so some folks had to make hard

choices because the, the articulate

885

that they knew and loved was no longer

what they thought it was anymore

886

because it was growing and changing and.

887

Taking on a whole new, really

exciting, uh, experience.

888

So I love it.

889

That's why I'm here.

890

Um, but yeah, it's not for everybody.

891

Tim Winkler: Yeah.

892

I, I've got so many more questions,

but I, I know that we're coming up

893

on the hour and we want to make sure

we get to our, our final segment.

894

What's that?

895

Toni Ann Careccio: You said that flew by.

896

It did fly by.

897

Tim Winkler: I want to ask one last

one and then we'll, we'll close with

898

the, um, five second scramble segment.

899

But what, what does the future of

customer success look like for you all?

900

Cause obviously AI is top of mind, you

know, everybody's trying to figure out

901

how this is going to impact their, their

jobs or role, um, Tony, I'll start with

902

you, you know, how, how do you see the

future of customer success evolving

903

as technology is obviously evolving?

904

Toni Ann Careccio: Yeah, I'll talk about

how it's evolving kind of at our company.

905

Obviously, we're doing, we're using

AI now and, and, and, you know, the

906

goal is always going to remain to

make sure our customers are happy

907

utilizing the system optimally.

908

Everything that I've already shared.

909

But it's the relationship building piece

that I'm really focusing on right now.

910

And so, you know, I think technology

is amazing and it's great and it

911

helps us in so many different ways.

912

However, for me in particular,

I'm still servicing a very old

913

school industry trucking, right?

914

And I think that relationship part

of the equation is really important.

915

These companies don't want to

look at us as just tech providers.

916

They want to look at us as partners.

917

And so something that I'm really

making a point to do, you know, the

918

end of this year, going into the next

couple of years is actually more on

919

sites, visiting, visiting customers.

920

So our CS team is actually required.

921

To, um, travel and visit their customers

for a day or 2 out of a time and

922

shake hands and sit down and make sure

they're utilizing the system correctly.

923

And they're happy and get them some coffee

and just like, actually work on building

924

the relationship because I think it's the

relationship piece of it that ultimately

925

leads to all these other factors.

926

Upsells and expansions and renewals and

all these and all these different things.

927

So that's really going to

be my concentration over

928

the next couple of years.

929

Mike Gruen: If I can jump on that for

a second, I strongly encourage if you

930

have a product designer that they also

do some of those onsites and go with

931

them and see how the people are actually

using the product that they're designing.

932

I think it's a great, great

933

Toni Ann Careccio: advice.

934

Tim Winkler: How do you kind of

see the future of customer success?

935

Romaine Buck: Yeah, I think you touched on

it when you said AI, because everybody's

936

talking about it, but everybody has

a different idea of what it can do.

937

And one of the things that

we've been really thoughtful and

938

deliberate about is making sure

that AI isn't going to replace AI.

939

People's jobs, but will help people do

their jobs better and more efficiently.

940

And so the product that we've launched

out in the market is designed to do that.

941

But we're also thinking about how can

we use a I within our customer success

942

team to Help our team be more efficient

and help us scale because you can't

943

throw bodies at all of your problems.

944

You know, we've been had way

more accounts than we've had

945

people for the longest time.

946

And although everyone would

love to hire more, it's not.

947

Realistic to hire your way out

of those sorts of situations.

948

So thinking about using technology

like AI to help the team work more

949

effectively and at a more broader scale

is something that's top of mind for me.

950

And we've been looking at some different

software opportunities to really try

951

to figure out what makes the most sense

for us, something that will, uh, surface

952

insights, uh, about our customers.

953

From all of the different places that

it lives and bringing it together into a

954

centralized location so that the team can

save time and having to go from Looker

955

to Salesforce to outreach to all of the

places and just have it all be there.

956

So I think The teams that are able

to leverage technology to help really

957

synthesize all of the data that's required

to ensure an awesome customer experience

958

are the ones that are really going to be

leaps and bounds ahead as we go forward.

959

Tim Winkler: Uh, it's a great, uh,

great point to kind of close on.

960

I think that was a, a fun

conversation, super educational.

961

I know I learned a ton about, uh,

customer success and, um, you know, we

962

might have, we're going to need to have

a follow up on this because there's a

963

lot of questions I left on the table too.

964

But I want to, I want to try to, to,

to get this last segment knocked out.

965

It's a fun one.

966

It's called the five second scramble.

967

Uh, we're going to rattle off a

couple of quick hit questions.

968

Try to answer within five

seconds, uh, if you can.

969

And, uh, Mike, you lead us off, um,

with Romaine and then I'll get Tony.

970

Sounds

971

Mike Gruen: great.

972

And I'll try to be quick.

973

Ready?

974

Here we go.

975

Uh, explain articulate as

if you were a five year old.

976

Romaine Buck: Uh, it helps, uh, people

build trainings so people can work.

977

Mike Gruen: What's your

favorite company value there?

978

Romaine Buck: Oh, wow.

979

Um, we're all works in progress.

980

Mike Gruen: Oh, I like it.

981

Uh, what's one customer success metric

that you check every day, every morning?

982

Romaine Buck: It is turn,

983

Mike Gruen: uh, what type of

person thrives that articulate

984

Romaine Buck: someone who's

comfortable with change, but

985

also has a really good heart.

986

Mike Gruen: Nice.

987

Uh, what's the best piece of

advice you've ever been given?

988

Romaine Buck: Be vulnerable.

989

It's okay to not know all the answers.

990

Mike Gruen: That's a good one.

991

Uh, what's something you did as a, did as

a child that you still enjoy doing today?

992

Romaine: Oh gosh.

993

Romaine Buck: Um, Oh, going to the beach.

994

I love doing that.

995

I grew up in Miami, and so that was always

a ton of fun, and I love a good beach.

996

Romaine: Pirate Festival

997

Mike Gruen: Um, so this is my, this

is my personal favorite question.

998

Uh, what's the largest land animal you

think you could take in a street fight?

999

Uh,

00:50:30,460 --> 00:50:31,530

Romaine Buck: hopefully a kitten.

00:50:31,530 --> 00:50:32,720

Nice.

00:50:32,720 --> 00:50:35,100

Romaine: Not just

00:50:35,100 --> 00:50:36,289

Mike Gruen: a

00:50:36,370 --> 00:50:36,740

Romaine Buck: cat,

00:50:36,740 --> 00:50:36,859

Mike Gruen: a kitten.

00:50:36,860 --> 00:50:38,320

A kitten, right.

00:50:39,030 --> 00:50:39,370

Love it.

00:50:40,150 --> 00:50:40,730

Romaine Buck: A kitten.

00:50:41,850 --> 00:50:44,220

If you have cats, you

know they're ferocious.

00:50:44,220 --> 00:50:44,840

That's true.

00:50:44,840 --> 00:50:49,720

Mike Gruen: Um, uh, what's something

you hate doing but are really good at?

00:50:51,605 --> 00:50:53,165

Romaine Buck: Oh, um,

00:50:58,115 --> 00:51:01,315

I think I, I hate public speaking,

but I'm pretty good at it.

00:51:01,405 --> 00:51:01,835

Nice.

00:51:02,315 --> 00:51:05,315

Mike Gruen: Um, what's a, uh,

that's a good one to be good at.

00:51:05,645 --> 00:51:05,885

And.

00:51:06,975 --> 00:51:13,975

Even whether you love it or hate

it, what's a charity or a corporate

00:51:13,975 --> 00:51:15,645

philanthropy that's near and dear to you,

00:51:17,625 --> 00:51:18,765

Romaine Buck: the junior league.

00:51:18,775 --> 00:51:23,165

So, I've been a part of that here

in South Dakota for the last few

00:51:23,165 --> 00:51:26,335

years, and it really is about

empowering women to empower their

00:51:26,335 --> 00:51:28,565

communities through different.

00:51:28,805 --> 00:51:29,955

Philanthropic works.

00:51:29,965 --> 00:51:32,495

And so I love that it gives

leadership skills to younger

00:51:32,495 --> 00:51:36,215

women, um, but also helps the

community in different ways as well.

00:51:36,255 --> 00:51:36,415

Nice.

00:51:36,675 --> 00:51:39,735

Mike Gruen: And last one, if you

could live in any fictional universe,

00:51:39,815 --> 00:51:41,085

uh, what universe would it be?

00:51:41,195 --> 00:51:42,525

Book, movie, doesn't matter.

00:51:42,895 --> 00:51:46,095

Romaine Buck: Oh, gosh, that's a good one.

00:51:47,495 --> 00:51:48,505

Holy moly.

00:51:49,245 --> 00:51:54,135

Um, I'm going to go with, I would, I

think it would be a ton of fun to live

00:51:54,155 --> 00:51:59,175

in the Marvel comic universe because

there's just so much going on, maybe

00:51:59,175 --> 00:52:00,705

in Wakanda or something like that.

00:52:01,015 --> 00:52:02,495

I think provided you're a superhero,

00:52:02,495 --> 00:52:03,605

Mike Gruen: if you're

one of the other people,

00:52:03,605 --> 00:52:04,696

Romaine Buck: not so

00:52:04,696 --> 00:52:05,242

Mike Gruen: good.

00:52:05,242 --> 00:52:06,334

Fair point.

00:52:06,334 --> 00:52:06,880

I

00:52:06,880 --> 00:52:11,793

Romaine Buck: mean, is that

not obvious that I would have

00:52:11,793 --> 00:52:12,338

Mike Gruen: superpowers?

00:52:12,338 --> 00:52:13,430

Romaine Buck: For sure.

00:52:13,430 --> 00:52:16,159

In the Marvel comic universe.

00:52:17,660 --> 00:52:18,030

Mike Gruen: Awesome.

00:52:18,060 --> 00:52:18,670

Well, thank you.

00:52:19,110 --> 00:52:19,550

Well done.

00:52:20,300 --> 00:52:21,150

Romaine Buck: Thank you.

00:52:21,210 --> 00:52:22,000

So fun.

00:52:22,350 --> 00:52:22,900

Tim Winkler: Great answers.

00:52:22,940 --> 00:52:23,180

Tony.

00:52:23,180 --> 00:52:23,390

You got a lot

00:52:25,590 --> 00:52:26,400

to live up to here.

00:52:26,440 --> 00:52:27,600

All right, we're going to jump in.

00:52:27,600 --> 00:52:30,300

So pitch PortPro to me as

if I was a five year old.

00:52:31,490 --> 00:52:37,830

Toni Ann Careccio: PortPro is a

technology company for trucking companies.

00:52:39,210 --> 00:52:41,230

Tim Winkler: Describe

the culture at PortPro.

00:52:41,990 --> 00:52:43,160

Toni Ann Careccio: I would say.

00:52:43,560 --> 00:52:51,200

Very family kind of oriented

entrepreneurial, um.

00:52:51,750 --> 00:52:53,540

Growth kind of mindset.

00:52:54,830 --> 00:52:57,840

Tim Winkler: What kind of

technologist thrives at port pro?

00:52:59,180 --> 00:53:02,710

Toni Ann Careccio: I would say

similar to what I just said people

00:53:02,710 --> 00:53:09,890

that are entrepreneurial minded that

can Have the mindset of rolling up

00:53:09,890 --> 00:53:12,450

their sleeves and just executing

00:53:14,270 --> 00:53:16,110

Tim Winkler: what kind of

roles are you hiring for?

00:53:17,520 --> 00:53:22,570

Toni Ann Careccio: Primarily right

now sales and offshore engineering um,

00:53:22,580 --> 00:53:27,415

however, we're going to be You Opening

00:53:29,435 --> 00:53:31,245

Tim Winkler: Describe

your morning routine.

00:53:33,005 --> 00:53:40,425

Toni Ann Careccio: Well, um, I would

say I wake up, I go to a, well, you

00:53:40,425 --> 00:53:43,695

know, do all the things, brush my

teeth, all, all, all that stuff.

00:53:43,755 --> 00:53:46,475

And then I have a personal trainer.

00:53:46,485 --> 00:53:48,915

So I think it's really important to.

00:53:49,455 --> 00:53:53,585

Fit that into my schedule because

it just really helps me, um,

00:53:53,675 --> 00:53:56,325

have good start to the day.

00:53:56,685 --> 00:54:00,865

And then I love coming home and

having showering, having my cup of

00:54:00,865 --> 00:54:05,635

coffee, and then I pretty much just

sit at my, sit at my computer all day.

00:54:07,095 --> 00:54:09,075

Tim Winkler: What uh, what's

your favorite app on your phone?

00:54:10,515 --> 00:54:11,055

Toni Ann Careccio: Ooh, Instagram.

00:54:12,555 --> 00:54:12,915

Tim Winkler: Okay.

00:54:12,925 --> 00:54:17,315

I think a lot of folks would agree

to, um, what's a charity or corporate

00:54:17,315 --> 00:54:18,565

philanthropy that's near and dear to you?

00:54:18,565 --> 00:54:18,605

Instagram.

00:54:19,915 --> 00:54:22,325

Toni Ann Careccio: Um, you know,

there's not a particular charity

00:54:22,335 --> 00:54:23,885

that I'm involved in right now.

00:54:23,895 --> 00:54:30,425

However, I do try to, um, always donate

when there's something, when there's

00:54:30,425 --> 00:54:34,105

a cause, um, that maybe a friend

or family member comes to me with.

00:54:34,695 --> 00:54:35,115

Tim Winkler: Nice.

00:54:35,485 --> 00:54:37,925

Do you get to have dinner with

any celebrity past or present?

00:54:37,955 --> 00:54:38,815

Who would it be with?

00:54:42,355 --> 00:54:44,535

Toni Ann Careccio: That's

so tough to pick one.

00:54:45,065 --> 00:54:46,775

Um, I would say.

00:54:48,740 --> 00:54:51,580

Maybe Elon Musk

00:54:53,590 --> 00:54:57,570

Tim Winkler: had that answer before to

an interesting, uh, interesting human,

00:54:57,570 --> 00:55:01,869

Romaine: very

00:55:02,150 --> 00:55:02,840

Romaine Buck: diplomatic.

00:55:03,410 --> 00:55:03,450

Toni Ann Careccio: What's

00:55:03,490 --> 00:55:06,650

Tim Winkler: the, uh, what's the worst

fashion trend that you've ever followed?

00:55:07,220 --> 00:55:08,050

Toni Ann Careccio: Oh, my God.

00:55:08,200 --> 00:55:14,590

Um, God, there's so many, maybe like.

00:55:15,810 --> 00:55:18,420

I don't know, like low cut

jeans that I don't know.

00:55:18,420 --> 00:55:20,225

Last

00:55:20,225 --> 00:55:22,029

Tim Winkler: one.

00:55:22,410 --> 00:55:24,530

What was your dream job as a kid?

00:55:26,300 --> 00:55:31,470

Toni Ann Careccio: It was to be a

backup dancer for big artists like

00:55:31,490 --> 00:55:33,550

Britney Spears or Spice Girls.

00:55:34,860 --> 00:55:35,400

Tim Winkler: Love that.

00:55:35,780 --> 00:55:36,090

Toni Ann Careccio: Yeah.

00:55:36,090 --> 00:55:36,440

Tim Winkler: All right.

00:55:36,785 --> 00:55:38,925

Uh, we're going to wrap on that note.

00:55:38,935 --> 00:55:41,965

Thank you both so much for, for

joining us and sharing your, your

00:55:41,965 --> 00:55:45,285

journeys with us and educating us on

the critical role of customer success.

00:55:45,695 --> 00:55:48,035

Uh, thank you for hanging

with us on the pod.

00:55:48,035 --> 00:55:48,345

Thanks

00:55:48,345 --> 00:55:49,274

Toni Ann Careccio: for having us.

00:55:49,275 --> 00:55:50,485

Thanks so much for having us.