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

Tim Winkler: 00:00:05

Welcome to The Pair Program from hatchpad, the podcast that gives you a front row seat to candid conversations with tech leaders from the startup world. I'm your host, Tim Winkler, the creator of hatchpad. And I'm your other host, Mike Gruen. Join us each episode as we bring together two guests to dissect topics at the intersection of technology, startups, and career growth. Welcome back to The Pair Program, everyone. Tim Winkler here with Mike Gruen. Mike, um, Halloween is, is right around the corner and, uh, Google just recently released their top trending costumes that are being searched for Halloween in 2024. So they've got any character from Beetlejuice, any character from Inside Out 2. Ray Gunn, the Australian break dancer from the Olympics with the green and yellow tracksuit. That seems legit. Pop star Sabrina Carpenter, uh, who I'm sure you and I, I don't, I have no idea who that is. Um, and then Wolverine and Deadpool for a duo costume. So of those options, you know, what are you going with? Beetlejuice

Mike Gruen: 00:01:14

all day. There's so little doubt. And see, I mean, yeah, Beetlejuice. Yeah. Have you seen the movie? Not the I saw the original one. Yeah, I saw the original. I haven't seen the new one.

Tim Winkler: 00:01:25

Oh, OK. Well, the new one's supposed to be pretty good. I'm sure I was hoping you were going to go with the the duo costume. You'll be Wolverine. I'll be Deadpool. Oh, yeah. Missed opportunity. I just a little collab. Yeah. Now I'd totally be down next. I think we both have to dress up because I think we'll have one right, right around Halloween. Sounds good. Um, what about you ladies? What are you going with any, any, any of those that jump out to you?

Romaine Buck: 00:01:54

That was quality for sure. I would also do, I think something Beetlejuice related. And I did see the second movie as well. And it is Hilarious. It is so good. There are a couple scenes in there that I was just laughing out loud. So unexpected kind of fun. I'm going to see,

Tim Winkler: 00:02:11

I'm always just annoyed by critics. Like everybody just wants to give bad reviews these days. I feel like, and so like everybody bashes it, but you know, Tim Burton's a genius and you kind of know what you're getting with anything he puts out, you know? So I

Toni Ann Careccio: 00:02:24

mean, I'm a review snob and I think talking to two CS people here, I think we're both very much into reviews.

Tim Winkler: 00:02:34

I'm a big review person, but I, I just know that like, there's a lot of negative, like the more, the more reviews that are usually going to be negative are going to be the ones that people want to check out. Well, that's because that's what

Mike Gruen: 00:02:45

people click on. So that's the problem. Yeah. That gets reversed against clicks. And that's, that's,

Romaine Buck: 00:02:51

it seems like all the people that are doing reviews now are people you've never heard of from a publication you've never heard of from a thing you've never heard of. Right. Is it some dude in his basement? Just two dudes on some podcast somewhere.

Tim Winkler: 00:03:04

Yeah. I actually think it's just a bot. I don't even think it's a real person. It's just a bot out there. Yeah, just stirring something up. Alright, well, we'll have a follow up episode about reviews here at some point. But let's give the listeners a little Q& A on what today's episode is all about. Today we're going to be talking all about customer success teams, um, specifically building and scaling customer success teams and kind of growing startup environments and how that might differ from larger organizations as well. Uh, so in true program fashion, we, we do have two excellent guests joining us to approach the conversation from a few different perspectives. Our first game, uh, first guest, Romaine Buck has experienced transforming customer service teams into. Customer success teams at companies like Articulate and LinkedIn. She's currently the vice president of customer success at Articulate, a workplace training software company that provides online training courses. And we have Tony Pizzano, a repeat kind of startup founder and currently the chief customer officer at PortPro, a startup that's building a transportation management software for the trucking industry. Uh, important to note that Tony built out Port Pro's customer support and customer success teams, which I'm sure we'll expand on in our discussion. So Romain and Tony, thank you both for joining us on the pair program.

Romaine Buck: 00:04:26

Thanks so much for having us. Awesome.

Tim Winkler: 00:04:29

All right. Now, before we dive in, uh, we do, uh, kick things off with our pair me up segment. So here's where we'll all go around the room and spit ball a complimentary pairing of your choice. Mike, you kind of lead us off what, uh, what your Pairing for today. Yeah. So mine's

Mike Gruen: 00:04:43

a little on the weaker side. Uh, but over the weekend, you got to set the expectations low, uh, over the weekend. Uh, I, my son and I were down in DC, uh, looking at, uh, colleges and on the tour on the college tour, I was reminded of how much free stuff is in DC. So that's my pairing is the DC, this DC and free stuff. You have access to all these museums. Um, the Smithsonian and so on and so forth. There's all of these great things in DC and resources, um, that really put it like as a top notch city from that perspective. And you sort of think about New York city. It's like, you know, you want to go to a museum that's going to, you know, you have to give a pretty big donation. So, um, DC and, and, and free stuff, um, DC free stuff.

Tim Winkler: 00:05:27

Sometimes it doesn't feel like that. No, definitely not.

Mike Gruen: 00:05:32

And not all museums are free. Uh, but yeah, true. But the Smithsonian does, but there you go,

Tim Winkler: 00:05:37

I will say I'm a huge fan of the fact like a lot of those museums are free because it just encourages you to go and kind of learn something new and, um, something I kind of slack on when I get, get my family, my daughter out there a little bit, uh, she's a little young, but when, when she gets a little bit older out there to To experience it. And you're right, save some, save some money, uh, while you're doing it. Yep. But you'll probably pay for it in parking though. No, well, no, you, I mean, you take the, take the,

Romaine Buck: 00:06:01

take the train. We're all paying for it in

Mike Gruen: 00:06:03

taxes, so it's just pay for it in your tax dollars at work. So you might as well take advantage of it. Okay. All right. Do DC and free stuff. There you go.

Tim Winkler: 00:06:12

Um, I'm gonna queue up my Hold on here. Oh, there's props. I love it. Got a prop leaning. I got prop for this one. Alright. Um, I'm gonna go with this is. Kind of difficult now. Um, I'm going to go with island life and pirate parties. So my family and I, we've been living the last month on a small island off the coast of Georgia. It's called Tybee Island. And, you know, it's for us, you know, we're not just vacation. We're working, we're living in a, in a, in a different destination, but, uh, you know, fortunate to be able to do so. But, yeah. Very different environment than the high speed lifestyle from back home in Northern Virginia. And so we, uh, every, every year, apparently this, this island, they host something, uh, in October called pirate festival. And I'll just say that this entire island goes all in for this pirate fest. And it's pretty amazing to see, but they've got a parade. They've got, uh, something called the Buccaneers ball that they kick off with from like Thursday to Sunday where they name like a pirate King and a pirate queen. And everyone's dressed head to toe and like legit pirate garb. So of course we had to wrangle together like costumes and participate. And, uh, it was just a really interesting, amazing time. Uh, to the point where I think we're going to try to make it an annual tradition and come back out here.

Toni Ann Careccio: 00:07:32

Uh,

Tim Winkler: 00:07:36

you know what, I, there's so many things on the agenda that we only kind of made it to a few things. A treasure hunt sounds. Pretty obvious. I know there's a lot of bar crawls. It's a big drinking, uh, island, apparently. And I think, you know, that's kind of the pirate way is,

Romaine: 00:07:53

uh,

Tim Winkler: 00:07:53

you know, roll around, you know, uh, it's kind of open, open container policy too. So everybody's just kind of bouncing around. Um, but yeah, that's, that's going to be it for me. I'm going to go with the island life and pirate parties. And I recommend anybody, Check out, uh, Tybee Island if you're out here for third weekend in October.

Romaine Buck: 00:08:12

I love that. If, if you're pirate people, you have to try out Disney Cruises because they have Pirate Night every time you go on a Disney Cruise. And every, same thing, everyone is in full garb. Oh, that's fun. And they have like all kinds of fun activities. It's a good time. And if, and I did my first Disney Cruise two years ago and it was, Around Halloween time. So that's awesome. Dooms everywhere, which was fantastic. Not only were all the characters in costume, but all of the adults and the little people. And it was a ton of fun. And I don't even have kids. And I was

Tim Winkler: 00:08:45

just going to ask. That's so fun. Did they tell you in advance? So like, you know, to go and get your pirate garb in advance?

Romaine Buck: 00:08:52

Yes. They tell you in advance. Okay. That's, that's cool. There's all always pirate night. And then if you're a slacker like me, you can also, they pass out like bandanas. So at the very least you have a bandana nice to hook you up for for pirate night. Yeah.

Tim Winkler: 00:09:06

All right. Well, I'll have to remember that. 'cause, uh, now that we have a a, a young child, it'll, you know, we can, we can go on the Disney cruise. Well, you said you went, you went out there as well. I mean, I imagine it's just, uh, pretty much parties for adults, kids, everything, huh?

Romaine Buck: 00:09:20

Absolutely. And what I also really loved about it is they have areas for kids. So you can take your kids to like the kiddie daycare, depending on what age they are. And then you, there were so many adults that I met who were like, I don't know where my kids are. They're at the imagineering thing. I haven't seen them since. Yeah. And the parents were, you know, having a blast. So it's a good time and you

Tim Winkler: 00:09:43

don't have to drive home

Romaine Buck: 00:09:44

and you don't have to do anything you

Tim Winkler: 00:09:48

Awesome. All right. Some good recs for the listeners. Um, let's pass it over to our guests, uh, for their intros and pairings. Um, Romain, maybe just a quick intro from you and your pairing.

Romaine Buck: 00:09:59

Yeah. I'm Romain Buck. I'm the vice president of customer success here at Articulate. I've been here about four years and prior to Articulate, I was the director of customer success. at sprout social, which was a social media management, um, software company. And prior to that, I was at LinkedIn, uh, and spent seven years there. And that's really where I moved into customer success from sales. So I'd been in sales and software since 2008. And then there came that point in time where I was like, Hmm, what else do I want to do here? And I realized that the thing that I loved most about selling was. Helping customers have that aha moment and make those connections and helping them be successful, which became customer success and haven't looked back. It's been fantastic. And I would say my pairing, which is fresh from a week out in the Western part of the state. And I live in South Dakota now it would be road trips and good tunes because driving five and a half hours through. The planes that are South Dakota. You need good music to keep you going. So I would say it'll make or break your road trip for sure.

Tim Winkler: 00:11:12

Uh, it's spot on. Yeah, we did a road trip cross country and we, we, uh, went from Chicago to South Dakota and that's a long, A long road of nothing, uh, a lot of, uh, like solar, you know, uh, wind turbine farms and whatnot. Uh, what's, what's your playlist, what, what kind of music are you jamming out to on the road trip?

Romaine Buck: 00:11:35

Anything that you can sing along to. So that goes from pop music to nineties hip hop to just good old fashioned, like, yeah. 80s tunes as well. I love it. And I know that road trip from Chicago to South Dakota because I made it many times. I moved here from South Dakota, from Chicago about five years ago. Four years ago now and, um, was building a house here. So I was driving back and forth and that is eight hours of not good times. A lot of music. Yeah. Windows

Tim Winkler: 00:12:09

down, music, stay, staying awake. I mean, that's, that's pretty key.

Romaine Buck: 00:12:14

Awesome.

Tim Winkler: 00:12:14

I dig it. That's a great pairing. Um, uh, Tony, how about yourself? Quick intro and your pairing.

Toni Ann Careccio: 00:12:19

Yeah, so, um, I'm Tony. I am the chief customer officer at Port Pro, which is an operating system for the dry age industry. Drayage just means the type of trucking where you're transporting containers in and out of the ports and the rail, the rail yards. Um, I lead our customer success team. I also lead our marketing. And I have a pretty, I would say, nonlinear career path. I grew up with a family business in trucking, but, you know, went to college as a dance major. And then I worked on Wall Street for 4 years on a trading desk. And then after that, I started my 1st, um, I co founded my 1st tech company called Axel, which was a software company in trucking. And then I, after that company was acquired, I joined a venture capital firm where I was investing in supply chain and logistics tech companies. And then I kind of rekindled with my cousin who is the co founder of Axel with me and we started PortPro. And, um, yeah, I've done everything in the company from leading our sales team to, Oh, wow, we have a lot of sales. How do we implement the software, right? To kind of overseeing our onboarding and then our support. And now I'm really happy to be in customer success and marketing. I would say for my pairing. I am really into mindset and wellness. And so one of my favorite activities is hot yoga. So I'm pairing like saunas with, with yoga. And it's one of my, one of my favorite activities.

Tim Winkler: 00:13:57

Intense. One of the most intense, intense workouts I've ever done was, I felt like I was dying, honestly. Yeah. I'm not a yoga.

Romaine: 00:14:07

I do not want to. I'm

Tim Winkler: 00:14:08

just kidding.

Toni Ann Careccio: 00:14:08

Yeah, basically. Yeah.

Tim Winkler: 00:14:12

But, you know, you, you, you walk away from it and you feel

Toni Ann Careccio: 00:14:15

like a million, a

Tim Winkler: 00:14:16

million bucks. Yeah.

Toni Ann Careccio: 00:14:17

Yeah.

Tim Winkler: 00:14:18

Yeah. Um. That's great. I like the pairing and, uh, your background. I'm really, I'm really excited to bring to the conversation because you've, yeah, you mentioned it's such a diverse background. So you're, you're approaching customer success from, you know, looking through multiple different lenses, which is going to be a great addition to the conversation. And so I want to make the most of our time and, um, uh, jump into it. So. Thank you. Uh, let's, let's, let's transition at the heart of the discussion at this point. So like I mentioned, we're, we're talking all about customer success teams in today's episode, and so we're going to have each of our guests, I mean, they already kind of gave us a little bit of a brief overview on, you know, their introduction into customer success, but expand a little bit on that, um, we'll define, you know, what. They think customer success is and how it differs from customer service. Uh, we'll explore like, when is that right time to start building out a customer success team? Uh, how to kind of structure and scale these teams. And we'll close with some thoughts about the future of the space as well. So, um, Romain, let's, let's start with you. You kind of gave our listeners a little bit of a back backstory on, on your journey into, to customer success. You know, you can expand on that a little bit more or, or just jump right into, you know, how you define customer success and, you know, how that definition has evolved over, you know, the, your tenure in different roles throughout your career.

Romaine Buck: 00:15:39

Yeah, I think it's super interesting because customer success is still pretty new as, uh, A job, if you will, when I was at LinkedIn, actually, um, and I took my first customer success job, the job was called, um, solutions, product consultants, uh, and that was because our director at the time didn't feel like we had all of the right elements yet to call it customer success. And as we evolved our business and the way we were interacting with customers, we kind of. earned the title of customer success. And for me, customer success is really thinking about how to obviously, um, gain maximum R. O. I. Because that's what we always want to do. That's why we're here while helping your customers reach their goals. And goals. So in order to do that, we have to know why did they come to us in the first place? Why did they buy and articulate? We are a an E learning software platform. And 1 of the things that I talked to my teams about all the time is it's overly simplistic to say people come to articulate because they want to create E learning. Sure, they do. But the question is why when we understand the why behind what's motivating our customers to come to us, then we know how they're going to measure us. And then we know how to help them be successful. And until you understand what a customer wants to truly accomplish, uh, you're not going to be able to help them be successful. And I love the equation that Tony, you've probably seen this from Gainsight. It's CS equals CX plus CO. Customer success equals customer experience plus customer outcomes. And that CX part, that customer experience, that every person within an organization, not just the CS team is responsible for the customer experience, whether it is marketing or the sales team or the product team or the finance team and the support team, everybody that your customer interacts with. As a hand in that customer experience, and then you pair that with what are they trying to get out of this? What's the outcome when you get those things right? Then you help your customers be successful. And that is I will live and die by that. And I think it's super important. I'm very different than customer service, which is. Something's gone wrong. Let me help you fix it. It's super transactional and super reactive and something's already gone wrong when they're coming to the customer service team. Um, customer success should be proactive. We should be understanding what our customers are trying to accomplish and helping them get there. We shouldn't be waiting until something's broken before we're reaching out and connecting with our customers. And so that's how I kind of keep those two things different.

Tim Winkler: 00:18:33

I just think it's so fascinating how it's like a fairly new ish department and, and, uh, you know, kind of role or, or team, um, just for context for, for our listeners, cause I want to, you know, kind of make some comparisons to, with Tony's, um, you know, kind of company size and everything else articulate from a headcount perspective, can you just kind of give us an idea of what, where you all sit and then what's the size of the customer success team?

Romaine Buck: 00:18:59

Yeah, so articulate. We've got just under 500 employees right now, and we are fully remote. Always have been always will be. We've never had an office. So that makes it a little bit of a unique culture as well. And the CS team. So I started 4 years ago here. We had 10 people on the CS team. And now at the end of this year, we'll have almost 40. So we've really been able to grow and scale and do some amazing things. And really, part of my journey is helping people. Transition this team from what was truly 100 percent reactive to being more proactive and being more of a trusted customer advisor and consultant for our customers and getting out of that vendor box.

Tim Winkler: 00:19:42

Yeah, that's great. Somebody once told me like a sales hack that if you're looking to identify like prospects, some really successful companies, look for companies that are hiring customer success folks right now, because usually they're scaling their customers as well. So it's a, uh, it's a good, a good area to be in, you know, you're, you're obviously front and center and working closely with, with the customer. And, and like you mentioned, maximizing that ROI. So I think it's a really, really great, uh, you know, department, uh, to, to be a part of a growing company. Uh, Tony, let's, let's kick it to you real quick and, you know, maybe a little bit more on, on how you approach customer success and how you, how you see it and how you're, how you're building out those teams at Port Pro.

Toni Ann Careccio: 00:20:22

Yeah. So just for perspective, we are about 150 employees globally, I would say about. 80 to 90 of those people are based in the US and then the others we have offshore offices and so 150 employees and about 8 of those folks right now are include the CS department. So, to remain point, I think it's really interesting that the term customer success really just kind of became a thing. Over the last, I don't know, 5 or so years, it's really just become such an important part of companies, specifically technology companies. I think, um, you know, when you look at a lot of the studies, it shows that acquiring a new customer can cost. 5 to 7 times more than retaining an old 1. I think that, of course, depends on the industry you work in, but it really just. Makes you realize how important. Retaining your customers are and so that's my job at 4 pro is making sure, um, You know, our customers are happy that they are utilizing our system and the different features within our system, but not only utilizing the features using them correctly. So, making sure that they're, um, optimizing their operations with the tools that we provide. Um, our team is really involved in making sure that. Our customers are, um. Like I said, happy, but, um, achieving their goals. So one thing that we do really often when we're onboarding a new client is we are asking them, hey, why did you sign up with us? Right? What are your goals as a company? And throughout the implementation process, the goal is really just to get their system stood up, but then it becomes the responsibility of the customer success team to make sure that we're helping them achieve those goals. Thanks. And measure those goals. So, on every, you know, call or quarterly business review we have with our customers, we're looking at those initial goals that they set and helping them, you know, kind of evaluate where they are since implementing our software and what more needs to be done to help them achieve those goals. Um, we are really big in product led growth. The good thing, um, the cool and like differentiating thing about us is that, you know, our founding team comes from the dry edge trucking industry. So, we had a lot of experience and expertise on what was initially going to be built to help the companies. Achieve their goals. Um, however, as we get bigger and bigger, it's really important that we're taking our customer feedback and then ultimately looping that feedback into, you know, feature development in our in our products. And then the last thing I'll say, Romain, you, you touched on it, but for me, this might, this might be a good segue into the next question versus customer support, but customer success is really about being, being proactive.

Mike Gruen: 00:23:38

So I think the point you touched on both of you about the why is so important because, so I think back to, I was at a cybersecurity training platform company. We were. We had a customer success team. I worked very close with them to sort of support them and on board. And we were building all these data models to try and predict churn. And one of the things that was very interesting was that usage of the product by the admins sometimes meant. That they would churn and sometimes meant that they didn't, and it was really got back to the, like, why are you here? Like this idea of like, oh, I want to set it and forget it. If I never have to log into this thing, then it's working for me versus other people that were like, no, I want to be in there every day and twiddling with it and playing with it. And so knowing that you can't just look at the data and look at, like, are these features being used? And know whether or not that's going to be like a predictive thing. I think that

Romaine Buck: 00:24:26

is so

Mike Gruen: 00:24:27

true.

Romaine Buck: 00:24:28

That is so true. Yeah. Everybody's health score tells them something different and you have to understand what good looks like for your customers. And sometimes that varies by industry. So when I was at LinkedIn and we were selling, um, sales navigator as the product there, and We had a health score. We like to see 80 or above to indicate that our customers were healthy, but we noticed that all of our finance customers were like in the 30s. So they always were in the red, looked horribly unhealthy. And what we came to learn was when we talked to those customers, they'd say, no, it's great. This is exactly what I thought it was going to do. Their uses was just always going to be lower because of. Their industry, whereas other customers would be pushing 100. So it really is understanding what matters to your customer and then measuring accordingly and never going in thinking, well, this looks terrible. Oh my gosh, you're going to churn. Um, because. Sometimes they're totally happy with that. And

Mike Gruen: 00:25:34

right, which

Romaine Buck: 00:25:35

is,

Mike Gruen: 00:25:35

which is funny because I had a different experience where I was the customer. I remember talking to my customer success person every, every quarter. And she's like, yeah, I, you guys, you're at the top of the list. Like in terms of guys look great. You're getting lots of usage. And I'm like, yeah, just a reminder. Uh, we're not renewing the contract. Like it was like, we look so healthy, but at the end, it's just, and she's like, I know, I know what you guys are helping my numbers, right?

Toni Ann Careccio: 00:26:02

That's why relationship building is like one of the most important parts of a customer success function. Right. Because. You know, if your customer is not happy, they're going to come to you and talk to you because you've spent that time building the relationship with them. And it's really the sentiment right that I think. Is more important than just system system usage and I think. Without that relationship, you don't know what the sentiment of the customer is.

Mike Gruen: 00:26:33

And I think that's an important thing. I want to ask you guys how you build trust because so at one, I've worked at several different companies with different customer success and one company I worked at that we iterated that our head of sales churned a little bit. So there was a lot of iterations of what customer success looked like. And one of the challenges that one, one iteration had was they had a lot of quotas, they had a lot of expectation of sales and expansions, not just. Not just retention, which makes sense, but really about expanding and and it's sort of in talking to some of the people, it sounded like it put them a little bit of a conflict of interest in terms of like, how do I gain someone's trust when they know I'm just trying to like when they think I'm just trying to sell them on buying more or expanding? I'm curious how you guys sort of tackle that or what your thoughts are on that. Um, do you even see that as a, as an important part of customer success? Is that sort of expanding the, the just throwing it out there? I think

Romaine Buck: 00:27:29

that's such a great question and I do see that. And my team at articulate is a little different because when I started, the team not only had a retention number, but it also had an expansion number. And then as the sales team evolved, we moved that expansion number over to the sales team. So now the sales team is responsible for selling. More product than we just launched AI at articulate. And so they're responsible for selling that. We're going to be launching localization pretty soon, and they're going to be responsible for selling that. But if there's a partnership between success and sales that I think sometimes gets lost, sometimes gets a bad rap, but it's also always critical because you need to understand what your swim lane is and who is building the trust. Because the success team sometimes, my success team sometimes struggles with this idea of I'm not supposed to be selling to my customer. I'm supposed to be just making sure they're happy. And I'm the one that says, wait, we're in success. We are selling, we're selling every renewal. And so it's always important for us to make sure that The relationship you have, you are continuing to develop so that that sale, that renewal is a no brainer. And it's obvious and that we're uncovering opportunities for expansion so that we can intro our sales counterpart and that they can upsell really easily because the customer needs the thing that we're talking about. So it's not a smarmy kind of Sales motion. And that's the fear. I think that some folks have and a lot of customer success people, myself included, came from sales and didn't want to do that anymore. And so sometimes people have a fear that they're going back into sales when they're in customer success. Um, and every organization is different. I've been at other organizations where CS teams didn't have a quota at all. And it was really just about health and customer retention. And I've been at other organizations where. Their 100 percent was a number. Uh, and so I think how you build your team determines what those swim lanes are and how you build that trust to support that motion.

Toni Ann Careccio: 00:29:41

This topic for me, no, I was going to say this topic for me is just so relevant right now because, um, we just introduced. Our CS team actually owning upsells, so they've always owned renewals. And they've owned expansions, which in our definition is like, we charge based on the number of drivers a trucking company has. So, if they go from 10 drivers to 20 drivers. We expand the contract size. But there's really not a lot of sales motion there. It's like, you've just increased the number of drivers. So we're going to expand your contract. We just introduced the idea of upselling into different product lines and features. And at first the CS team was very hesitant about it. They had this like anxiety around sales and we really had to. Um, coach them, like, don't freak out over the quota or the number, right? You have to more so look at this as an opportunity to help your customer, right? You have the relationship with your customer. You know what products and features are using. You know what they're not using. You know what their goals are. And so, and you know what our product offering is, right? So if they're not using certain features, but those features are going to help them better. Um, you know, optimize certain areas of their operations, which will ultimately help them achieve their goals. It's like view it from more that lens than like, this is sales and I have to hit this quota, you know what I mean? So it's something like,

Tim Winkler: 00:31:19

you know, you have an ability to solve more of the customer's problems versus the one kind of problem that you were looking at. Do you think that breakdown,

Mike Gruen: 00:31:27

um, is a function of size because that going iterations, like the one, the team that I'm thinking about was smaller, they. It was the customer success people that were very much involved in those expansions. But the product offering was still something that they could sort of keep in their head. They didn't have to go. And then as we got bigger, and as we had more to offer, and as there was, they had more customers that they're trying to help. It went, it then switched more to what Romain was talking about, where we, they were, they were in. Account executives to come in and really help on the expansions because they were the product experts. And there was a lot of conversations that would happen before that. You know, obviously, Hey, this is the customer. This is what they use. This is what they don't use. But I wonder if, is it, is there something about the function of the size of the company or

Toni Ann Careccio: 00:32:10

It could be. What I know is that we've done. We, we, we test a lot of things, right? Like we do something. If it's working, we, we change and we see how that goes. And if that doesn't work, we change. We see how that goes, right? We try to move really fast in that regard. Um, and so for a while, our sales team and AEs owned the upsell process and. I don't know. I think that had its own limitations. 1. I think that was super distracting from the new business quotas that the sales team had to have to hit. Um, so I think it was distracting in that regards to, um, like I said, the CS team. I really try to make sure our success team is building strong, meaningful relationships with the customers and really understand their goals and usage. So it's like what better person to upsell something than the person that has a relationship, right? And knows where the company stands as opposed to the sales team, just trying to hit this quota, randomly calling a customer of ours when they really don't know the usage or the sentiment of the account to try to upsell them. It just didn't sit right with me. So we decided to make this switch, um, fairly recently. And so we'll see in the next, you know, three months, this, this quarter, how, how it actually goes, but I'm excited about it.

Tim Winkler: 00:33:33

It kind of leads me to it. You know, the next, next question I wanted to ask you all, because we have a lot of founders that are, you know, listeners that are probably in the very early stages and wondering when is that right time, right? Because at the. The early stages, right? The founders are usually the one that are doing most of the customer relationship. Um, when, when did you see that as the need to start scaling a team telling maybe you're, you're, you're a good one for this because you know, you've been with port pro from. Early on, um, you know, is there a number that you kind of figured out was like a ballpark 20, 30 customers? How do you determine, uh, when is that right time? And then how, how do you determine when is too much on one person's plate to, to justify expanding? This

Toni Ann Careccio: 00:34:17

is a great, this is a great question. I would say, It wasn't until we hit around 4 million, 3. 5 to 4 million in ARR where we started actually like building out our customer success team. Um, and then that's just scaled based on, you know, capacity, how many clients can I successfully manage, um, without being too overwhelmed. And it's like, okay, I'm too overwhelmed. Okay. Let's look at hiring another customer success manager. And it's kind of just grown organically. But up until that point, it's been the account manager leading the onboarding and our customer support team really managing, um, more of like the, the day to day sort of questions from the customer. But I would say it was around the 3 and a half. Million error mark, where we started. Building out our customer success team.

Tim Winkler: 00:35:14

That's fascinating. Um, uh, Romaine for you, you know, you've, you've been scaling the customer success teams that articulate, you said from 10 to, what do you say? 40 now or almost

Romaine Buck: 00:35:25

40. Yeah.

Tim Winkler: 00:35:27

So then, you know, how did you approach it for maybe, you know, this is more of like maybe looking at mid to later stage startup growth, you know, where, where did you come in and why did they bring you in? Did you come in as a VP or did you grow into that role?

Romaine Buck: 00:35:43

Yeah, I did come in as a V. P. And what was interesting was the customer success team was reporting in to the V. P. Of marketing when I arrived. And so customer success was 100 percent reactive. All of the interactions were basically going through marketo. And so there was this outbound motion through marketo and then the C. S. M. S. Would respond to customers through a Salesforce case queue. And that's what I walked into, um, four years ago and was like, okay, um, so we're going to try some different things. And it's been an interesting journey because one, it was. Uh, really getting the team to shift and think change their perspective about what customer success looks like, but also getting the organization to think about customer success differently too. So being the first dedicated customer success leader at articulate and having the experience of coming from some great organizations, I was able to come in and think differently. Uh, and we built segments to define segments. And so, whereas There were 10 people who would just pull cases out of a case queue and support whatever they wanted. So one day a CSM is working on Microsoft and the next day they're working on Joe's body shop sort of thing. And it was just because that's what they pulled out of the queue. So we created distinct books of business. Every CSM had an assigned book. We had a SMB, a mid market and enterprise segment, and just really kind of Started putting those foundational elements in place on. We've still been working through that. I built also the customer success enablement function as well as brought in customer success operations because these were gaps for the team. The team was doing their job, but there were skills that were missing. And so it was really clear that there was an opportunity to help the CSMs. Be better. C. S. M. S. And so that's where the enablement function came to play. And then operations as well. Of course, every organization has a sales ops function and sales ops was kind of taking care of the customer success team, but it's a very different ones. And so it became really clear that we needed someone whose focus was how to you. Build and optimize processes for our customer success organization. How can we run that? And so bringing those individuals in as well to help us really start scaling, uh, and really fine tuning some of the great work that was already happening to get us to this place. And I keep telling the team was what got us here. Won't get us there. I've been saying that for four years because we're still going. Um, But this idea that we have to be agile and we have to be open to learning and growing, uh, because we don't have all the answers. And Tony, I love that idea of working really fast and iterating. And so really trying to get the team to understand change is just part of the deal. And as you are trying something new, it might not work. And so we're going to try something else. We're not going to drag the dead weight and keep going in the wrong direction. Let's cut bait and let's go. And getting folks Comfortable with that, with that. Discomfort has been a big part of scaling this team as well. So we are doing something that we've never done before. We're going to build a team in Chile, uh, and they are going to take the very long tail of our business. So everything kind of sub eight K is going to move to that team and that's. What we're going to stand up by the end of the year, that will take the team to 40. So we're going to take all of that long tail business, move it over to this team in Chile. We'll be partnering with some of our sales counterparts that are here, and then that will free up our mid market segment and our enterprise segment and the rest of our, uh, Larger SMB segment to really have more of those strategic customer conversations that we want them to have is right now. Bandwidth is a challenge and I'm sure bandwidth is a challenge for everybody. Uh, and so making sure that we give them enough time to do the things we want them to do is also part of. We're from scaling this organization as well.

Toni Ann Careccio: 00:39:54

Yeah. Outta curiosity, because you mentioned segmenting by, um, you know, SMBs, mid-market, enterprise. Have you ever segmented by geography?

Romaine Buck: 00:40:03

No, I've never done that. Um, personally at, uh, when I was two jobs ago at LinkedIn, we were segmented by geo, but we were also segmented by revenue and some other things. So we were in the central region, which was. Minnesota all the way down to Texas. And then there was east and then there was west. So everybody in the office was working the same region, but then there were other, there about 14 other data points that we were looking at with our customers to determine what. Segment what team they went into as well. So we're not as sophisticated and articulate with our segmenting right now. So it's really just a revenue base. Um, but we're looking at ways to get a little bit tighter because there's a little bit of a misalignment between our CS segmentation and our sales segmentation. And we really want to get more tightly aligned so that we can make sure that the teams are partnering even better together.

Tim Winkler: 00:41:03

That's why I love, I love, uh, the two perspectives, cause I feel like, you know, there's some ideation happening here, but also like hearing how, you know, Tony, you approach it from the early stages to growth stage with your own man. I think it's just a fascinating, uh, kind of continuation of, of how the role and the department evolves. And I think this is just on cue with startup world in general, right? Is that. You, you might've come in at a certain stage where you're excellent. You're perfect for it. We see this a lot in product roles. And then you go through a big growth spurt and you hit, I mean, a big round of funding, you start adding on features. And maybe you aren't that, that, that, that good PM that you, you were in that earlier stage, you know, it's, it's always, uh, something that you have to, you know, adapt to, but also kind of be open and humble, like admitting that maybe you aren't the best person for this new, you know, kind of growth of the company, um, might not be as relevant for, for CS, but we see it a lot of other departments, um, I want to

Toni Ann Careccio: 00:42:03

say that's this like rich verse King theory. And I think everyone in the company, right. Whether you're a CSM, whether you're the CEO has to have that mindset where. It's like, okay, just because I'm the CEO right now, does it mean I'm the right fit to be the CEO when we are doing X amount of million dollars or more in ARR? Right. And I think it's important for. Everyone to really have that mindset.

Mike Gruen: 00:42:27

I think it's funny how many, so just across departments, mindsets, that mindset, the one of constant change, the iteration is the same in product and engineering, right? Like we're constantly going to be doing new things and you have to be comfortable with that change. And I still remember all the conversations with especially more junior people where they'd be like, Oh, I felt like I just totally wasted my time. It's like, no, like, Yeah, we didn't. Maybe that feature didn't hit right or whatever, but it wasn't a waste of time. It would only be a waste of time. If we didn't learn anything, then it would have been a waste of time. And so I think it's, it's interesting to hear you say almost the exact same things that you're dealing with with your departments in terms of that growth mindset and that constant change and be comfortable with the discomfort. Exact same things I'm saying to engineers and product people. So, um, That's startup life. It's

Romaine Buck: 00:43:13

startup life. It's so true. When some people get really comfortable in their space that they forget that we are working really hard and really fast because we're in startup mode. Articulate it's been around over 20 years, but I tell people it's like, we're the, we're in startup mode right now because the way that we think about the company has completely shifted in the last six years and so it was a perpetual product for. a good 15 years of that time and it's really been the last five, six years that we've been selling software. So this is where all of that change has been coming and people who've been here since the beginning, not everybody loved that direction. And so some folks had to make hard choices because the, the articulate that they knew and loved was no longer what they thought it was anymore because it was growing and changing and. Taking on a whole new, really exciting, uh, experience. So I love it. That's why I'm here. Um, but yeah, it's not for everybody.

Tim Winkler: 00:44:14

Yeah. I, I've got so many more questions, but I, I know that we're coming up on the hour and we want to make sure we get to our, our final segment. What's that?

Toni Ann Careccio: 00:44:23

You said that flew by. It did fly by.

Tim Winkler: 00:44:26

I want to ask one last one and then we'll, we'll close with the, um, five second scramble segment. But what, what does the future of customer success look like for you all? Cause obviously AI is top of mind, you know, everybody's trying to figure out how this is going to impact their, their jobs or role, um, Tony, I'll start with you, you know, how, how do you see the future of customer success evolving as technology is obviously evolving?

Toni Ann Careccio: 00:44:51

Yeah, I'll talk about how it's evolving kind of at our company. Obviously, we're doing, we're using AI now and, and, and, you know, the goal is always going to remain to make sure our customers are happy utilizing the system optimally. Everything that I've already shared. But it's the relationship building piece that I'm really focusing on right now. And so, you know, I think technology is amazing and it's great and it helps us in so many different ways. However, for me in particular, I'm still servicing a very old school industry trucking, right? And I think that relationship part of the equation is really important. These companies don't want to look at us as just tech providers. They want to look at us as partners. And so something that I'm really making a point to do, you know, the end of this year, going into the next couple of years is actually more on sites, visiting, visiting customers. So our CS team is actually required. To, um, travel and visit their customers for a day or 2 out of a time and shake hands and sit down and make sure they're utilizing the system correctly. And they're happy and get them some coffee and just like, actually work on building the relationship because I think it's the relationship piece of it that ultimately leads to all these other factors. Upsells and expansions and renewals and all these and all these different things. So that's really going to be my concentration over the next couple of years.

Mike Gruen: 00:46:24

If I can jump on that for a second, I strongly encourage if you have a product designer that they also do some of those onsites and go with them and see how the people are actually using the product that they're designing. I think it's a great, great

Toni Ann Careccio: 00:46:36

advice.

Tim Winkler: 00:46:36

How do you kind of see the future of customer success?

Romaine Buck: 00:46:43

Yeah, I think you touched on it when you said AI, because everybody's talking about it, but everybody has a different idea of what it can do. And one of the things that we've been really thoughtful and deliberate about is making sure that AI isn't going to replace AI. People's jobs, but will help people do their jobs better and more efficiently. And so the product that we've launched out in the market is designed to do that. But we're also thinking about how can we use a I within our customer success team to Help our team be more efficient and help us scale because you can't throw bodies at all of your problems. You know, we've been had way more accounts than we've had people for the longest time. And although everyone would love to hire more, it's not. Realistic to hire your way out of those sorts of situations. So thinking about using technology like AI to help the team work more effectively and at a more broader scale is something that's top of mind for me. And we've been looking at some different software opportunities to really try to figure out what makes the most sense for us, something that will, uh, surface insights, uh, about our customers. From all of the different places that it lives and bringing it together into a centralized location so that the team can save time and having to go from Looker to Salesforce to outreach to all of the places and just have it all be there. So I think The teams that are able to leverage technology to help really synthesize all of the data that's required to ensure an awesome customer experience are the ones that are really going to be leaps and bounds ahead as we go forward.

Tim Winkler: 00:48:28

Uh, it's a great, uh, great point to kind of close on. I think that was a, a fun conversation, super educational. I know I learned a ton about, uh, customer success and, um, you know, we might have, we're going to need to have a follow up on this because there's a lot of questions I left on the table too. But I want to, I want to try to, to, to get this last segment knocked out. It's a fun one. It's called the five second scramble. Uh, we're going to rattle off a couple of quick hit questions. Try to answer within five seconds, uh, if you can. And, uh, Mike, you lead us off, um, with Romaine and then I'll get Tony. Sounds

Mike Gruen: 00:49:01

great. And I'll try to be quick. Ready? Here we go. Uh, explain articulate as if you were a five year old.

Romaine Buck: 00:49:09

Uh, it helps, uh, people build trainings so people can work.

Mike Gruen: 00:49:15

What's your favorite company value there?

Romaine Buck: 00:49:18

Oh, wow. Um, we're all works in progress.

Mike Gruen: 00:49:21

Oh, I like it. Uh, what's one customer success metric that you check every day, every morning?

Romaine Buck: 00:49:27

It is turn,

Mike Gruen: 00:49:29

uh, what type of person thrives that articulate

Romaine Buck: 00:49:33

someone who's comfortable with change, but also has a really good heart.

Mike Gruen: 00:49:37

Nice. Uh, what's the best piece of advice you've ever been given?

Romaine Buck: 00:49:44

Be vulnerable. It's okay to not know all the answers.

Mike Gruen: 00:49:49

That's a good one. Uh, what's something you did as a, did as a child that you still enjoy doing today?

Romaine: 00:50:00

Oh gosh.

Romaine Buck: 00:50:02

Um, Oh, going to the beach. I love doing that. I grew up in Miami, and so that was always a ton of fun, and I love a good beach.

Romaine: 00:50:11

Pirate Festival

Mike Gruen: 00:50:17

Um, so this is my, this is my personal favorite question. Uh, what's the largest land animal you think you could take in a street fight? Uh,

Romaine Buck: 00:50:30

hopefully a kitten. Nice.

Romaine: 00:50:33

Not just

Mike Gruen: 00:50:35

a

Romaine Buck: 00:50:36

cat,

Mike Gruen: 00:50:37

a kitten. A kitten, right. Love it.

Romaine Buck: 00:50:40

A kitten. If you have cats, you know they're ferocious. That's true.

Mike Gruen: 00:50:45

Um, uh, what's something you hate doing but are really good at?

Romaine Buck: 00:50:52

Oh, um, I think I, I hate public speaking, but I'm pretty good at it. Nice.

Mike Gruen: 00:51:02

Um, what's a, uh, that's a good one to be good at. And. Even whether you love it or hate it, what's a charity or a corporate philanthropy that's near and dear to you,

Romaine Buck: 00:51:18

the junior league. So, I've been a part of that here in South Dakota for the last few years, and it really is about empowering women to empower their communities through different. Philanthropic works. And so I love that it gives leadership skills to younger women, um, but also helps the community in different ways as well. Nice.

Mike Gruen: 00:51:37

And last one, if you could live in any fictional universe, uh, what universe would it be? Book, movie, doesn't matter.

Romaine Buck: 00:51:43

Oh, gosh, that's a good one. Holy moly. Um, I'm going to go with, I would, I think it would be a ton of fun to live in the Marvel comic universe because there's just so much going on, maybe in Wakanda or something like that. I think provided you're a superhero,

Mike Gruen: 00:52:02

if you're one of the other people,

Romaine Buck: 00:52:04

not so

Mike Gruen: 00:52:05

good. Fair point. I

Romaine Buck: 00:52:07

mean, is that not obvious that I would have

Mike Gruen: 00:52:12

superpowers?

Romaine Buck: 00:52:12

For sure. In the Marvel comic universe.

Mike Gruen: 00:52:18

Awesome. Well, thank you. Well done.

Romaine Buck: 00:52:20

Thank you. So fun.

Tim Winkler: 00:52:22

Great answers. Tony. You got a lot to live up to here. All right, we're going to jump in. So pitch PortPro to me as if I was a five year old.

Toni Ann Careccio: 00:52:31

PortPro is a technology company for trucking companies.

Tim Winkler: 00:52:39

Describe the culture at PortPro.

Toni Ann Careccio: 00:52:42

I would say. Very family kind of oriented entrepreneurial, um. Growth kind of mindset.

Tim Winkler: 00:52:55

What kind of technologist thrives at port pro?

Toni Ann Careccio: 00:52:59

I would say similar to what I just said people that are entrepreneurial minded that can Have the mindset of rolling up their sleeves and just executing

Tim Winkler: 00:53:14

what kind of roles are you hiring for?

Toni Ann Careccio: 00:53:18

Primarily right now sales and offshore engineering um, however, we're going to be You Opening that up a lot more in Q1 of 2025.

Tim Winkler: 00:53:29

Describe your morning routine.

Toni Ann Careccio: 00:53:33

Well, um, I would say I wake up, I go to a, well, you know, do all the things, brush my teeth, all, all, all that stuff. And then I have a personal trainer. So I think it's really important to. Fit that into my schedule because it just really helps me, um, have good start to the day. And then I love coming home and having showering, having my cup of coffee, and then I pretty much just sit at my, sit at my computer all day.

Tim Winkler: 00:54:07

What uh, what's your favorite app on your phone?

Toni Ann Careccio: 00:54:11

Ooh, Instagram.

Tim Winkler: 00:54:13

Okay. I think a lot of folks would agree to, um, what's a charity or corporate philanthropy that's near and dear to you? Instagram.

Toni Ann Careccio: 00:54:20

Um, you know, there's not a particular charity that I'm involved in right now. However, I do try to, um, always donate when there's something, when there's a cause, um, that maybe a friend or family member comes to me with.

Tim Winkler: 00:54:35

Nice. Do you get to have dinner with any celebrity past or present? Who would it be with?

Toni Ann Careccio: 00:54:42

That's so tough to pick one. Um, I would say. Maybe Elon Musk

Tim Winkler: 00:54:54

had that answer before to an interesting, uh, interesting human,

Romaine: 00:54:58

very

Romaine Buck: 00:55:02

diplomatic.

Toni Ann Careccio: 00:55:03

What's

Tim Winkler: 00:55:03

the, uh, what's the worst fashion trend that you've ever followed?

Toni Ann Careccio: 00:55:07

Oh, my God. Um, God, there's so many, maybe like. I don't know, like low cut jeans that I don't know. Last

Tim Winkler: 00:55:20

one. What was your dream job as a kid?

Toni Ann Careccio: 00:55:26

It was to be a backup dancer for big artists like Britney Spears or Spice Girls.

Tim Winkler: 00:55:35

Love that.

Toni Ann Careccio: 00:55:36

Yeah.

Tim Winkler: 00:55:36

All right. Uh, we're going to wrap on that note. Thank you both so much for, for joining us and sharing your, your journeys with us and educating us on the critical role of customer success. Uh, thank you for hanging with us on the pod. Thanks

Toni Ann Careccio: 00:55:48

for having us. Thanks so much for having us.