1.6: Trent Mosley & Jaclyn Van: Every Customer Experience Begins with a Conversation

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This is a podcast episode titled, 1.6: Trent Mosley & Jaclyn Van: Every Customer Experience Begins with a Conversation. The summary for this episode is: <p>On this show, you've learned how to leverage conversations to build brand awareness and to book a meeting. But what about after the customer signs? </p><p><br></p><p>Once that contract gets submitted, the conversation is really just getting started, and Drift's enterprise account executive, Trent Mosely, and enterprise customer success manager, Jaclyn Van, know this best.</p><p><br></p><p>So in the spirit of Valentine's Day, we're highlighting the sales and customer success relationship. Drift's Trent and Jaclyn (fondly known as JV) join Sammi to talk all about how they work together to create a seamless customer experience that never misses a beat. Hear how Trent uses emojis to show his appreciation, why every sales message should be written with the long-term health of the customer in mind, and some of the biggest mistakes Trent and JV have made -- and how they've fixed them.</p><p><br></p><p>Like this episode? We'd love it if you could leave us a ⭐️⭐️⭐️⭐️⭐️⭐️ review! And make sure to subscribe, so you never miss an opportunity to learn more about starting conversations in the Revenue Era.</p><p><br></p><p>You can connect with Sammi and the Drift Podcast Network on Twitter @sammireinstein,@DriftPodcasts, and Trent and Jaclyn on LinkedIn.</p>
What the sales --> customer success handoff looks like at Drift
01:28 MIN
The mistakes Trent and Jaclyn have made over the years, and how they've fixed them
03:09 MIN
How sales and customer success can create a unified front
02:18 MIN

Sammi Reinstein: Hey, this is Sammi Reinstein, and you're listening to Conversation Starters. On this show, we talk all about bringing conversations back to B2B marketing and selling, because if there's one thing we know about doing business in the revenue era, it's that the best customer experience wins. Through the power of our own conversations with Drifters, customers, and special guests, we'll learn how to deliver a sales and marketing experience that puts the buyer first. Let's get into it. Hi Elizabeth.

Elizabeth: Hi Sammi.

Sammi Reinstein: How you doing?

Elizabeth: I am doing great. The sun is shining. I had a wonderful walk to the studio today. Saw a lot of dogs in Boston Common.

Sammi Reinstein: Oh, that's the best. That is definitely the best.

Elizabeth: It really puts a pep in my step.

Sammi Reinstein: Definitely. And when it's winter, anything to brighten my day, especially a dog, is just the cherry on top.

Elizabeth: It really is.

Sammi Reinstein: Did you do anything fun this weekend?

Elizabeth: Well, I call my mom every Sunday just to check in from the week. So I was doing that and it was a good conversation, but then my dad called me separately and asked me all the same questions again. And I love talking to them both. It's always a great time, but telling the same stories twice back to back is pretty tough.

Sammi Reinstein: It is tough.

Elizabeth: And definitely the second time I was like," Well, I told mom that I went to the story yesterday and I bought this," and he could definitely tell I was getting a little annoyed. But I was like," Can I just either talk to you both at the same time, or you guys talk to each other before you call me back to back?"

Sammi Reinstein: That is so funny. My parents actually get upset when I text one of them something but I don't text the other one, but I'm like," You guys are in the same home. I just assume that you both communicate."

Elizabeth: Yes.

Sammi Reinstein: What I'm saying to you both. And my dad has in an Android and my mom has an iPhone.

Elizabeth: Yeah.

Sammi Reinstein: I'm not going to put them in a group message. TI can't get the green text.

Elizabeth: Yeah. And then if you're a green text, you don't get the" hahas" or you like a message. It's very inconvenient.

Sammi Reinstein: Yes, the reactions are very important.

Elizabeth: Yes.

Sammi Reinstein: And I think that's a good segue into today's guests and what we're going to talk about. We have Trent Mosley from our sales organization and Jaclyn Van, also known as JV, from our customer success organization, and we're going to ask them some about how they communicate together.

Elizabeth: Yes. I'm so excited to have them both on, they are legendary in the drift company for how they work together. And I'm really interested to hear their secrets to success with all the sales to see us handoffs, because they're so important. As we said, no one wants to repeat themselves. And customers are just like me talking to my mom and dad.

Sammi Reinstein: Definitely. All right. Let's jump into it. JV, Trent, thank you so much for coming on the podcast today. I'm really excited to have you both. And this is our first duo guest episode that we're having, so very exciting. And I'm really excited to talk to you both today.

Trent Mosley: Yeah, I'm honored.

Jaclyn Van: Thanks for having us.

Trent Mosley: Yeah.

Sammi Reinstein: Of course. JV and Trent are OG Drifters. They are legends in the office, and I very much still look up to them both. So Trent and JV, can you please introduce yourself and what you do at Drift? Trent, we can start with you.

Trent Mosley: All right. I'll get things started for us. I'm Trent Mosley, Enterprise Account Executive over here at Drift. Man, OG, yeah. I've been here for almost three years now, which, I mean, I feel that definitely qualifies as OG in any startup tech world. So joined Drift about three years ago, came from a mind- body where I actually helped implement Drift there, fell in love with the product, the company. You all have great recruiting, so obviously poached me. Came here, and it's been a wonderful ride ever since.

Sammi Reinstein: Awesome. And JV?

Jaclyn Van: Well, Jaclyn Van, Enterprise Customer Success Manager at Drift. Also here for just over three years, so we feel old now, Trent.

Trent Mosley: Yeah.

Jaclyn Van: But yeah, came over from a company called Jebbit where they had implemented Drift a little bit as well on their own website. And DC actually came and spoke to our team over at Jebbit, and I was just kind of fell in love with the Drift vision and hypergrowth ever since.

Sammi Reinstein: I love it. I love it. And if you haven't been paying attention to their introductions today, we have Jaclyn from customer success and Trent from sales. And at Drift, we talk a lot about the marketing and sales relationship and how important that is. And it is so important, but I also want to shed some light on the customer success and sales relationship, because at the end of the day, you have to have a really smooth handoff process, and there's so much communication that goes into that. So I'm wondering if you can tell me a little bit about how the two of you work together.

Trent Mosley: Well, it really starts, obviously, on my end. Whenever we get a new customer, we sign that deal as a company, that's when it really starts off, that relationship. Jaclyn knows I am very adamant about making sure my team is very well informed on everything that was discussed in that sales cycle, what to expect for this customer, really making sure we're setting the proper expectations, not only post- sale, but making sure we're aligning with that post- sale as well. So from the get go, we sign that customer. Jaclyn knows I'll Slack her right away, like," Hey, looks like you just got another one of my customers. Get ready. Going to send some notes to the entire team." And we start hitting the ground the second that contract is signed and making sure we're aligned for the business and the customer right then and there. Jaclyn, I'll let you take over what that looks like on your end, because I don't know what it looks like from you all. If you see a slack from Trent again, you're," Oh God, here we go. He's going to send over all his notes." So I'll kick it off to you what that experience is like on your end from the beginning.

Jaclyn Van: Oh, it's so much fun working with Trent especially. His notes are legendary within the CS department. They're just so thorough. They're pretty long, which for us is helpful because we just want to get as much context as we can. And of course we record our calls at Drift through Gong. So we're listening to Gong calls, certain snippets, but with Trent, a lot of that's just already in the notes for us, which saves a ton of time. So as a CSM with a whole book of business, that's super helpful. And then yeah, it's so funny because I usually get assigned to the account. I get the alert from Salesforce and in my inbox, and pretty much about the same time, I get a slack from Trent, a ton of emojis, super excited. So it's always a good feeling to know that it's someone who's that excited about the customer they just closed and how they're going to bring their context and everything that went on during the deal process over to our initial results call, and really our initial review call as well. So yeah, that partnership is great.

Trent Mosley: Definitely a lot of emojis.

Jaclyn Van: Yes.

Sammi Reinstein: Emojis are a really big thing at Drift, and I always feel like I have to tell the new hires what certain emojis mean. So yes, definitely big into emojis. So I want to lean in a little bit more to what Trent said earlier. So Trent signs a new customer. Amazing, we hit the gong, the virtual gong. We send emojis in Slack. Yay. What does that workflow look like, JV, from when you get assigned that customer? Can you walk us through a little bit more what those notes are and then how you transfer that to, let's say, that first call with the customer?

Jaclyn Van: Sure. So when I see those notes, I think the things that are helpful, first and foremost, are a bit of an org chart. So who was the champion that Trent was working with at the customer that really helped get the deal across, or champions? Who's going to be using Drift from a power user perspective in terms of building up the playbook, setting up targeting, really being in the weeds in that perspective, usually from the marketing side? And then what's the sales team's build out? How many reps do they have? Who's going to be using Drift first? What's important to them? And then just hitting into, what are their goals from at least the eye level? Trent usually gets a few layers deeper, which is always really helpful too, in terms of having more specific and quantifiable goals, which has been great. But then also just carrying that forward into the kickoff of" Hey, what, if any, concerns came up? What, if anything, should I be aware of?" Just so I know I can speak to that and address that with a customer during the kickoff call and beyond.

Sammi Reinstein: Yeah. And that first kickoff call, that first conversation, is so important to both of you, really our trusted advisors throughout this process. And we talk a lot about from a marketing perspective, personalization, but it goes through to sales and to CS, the show me you know me. If you get onto that kickoff call, it's a really bad look for us if it just looks like we didn't really do our homework.

Jaclyn Van: Oh, could not agree more.

Trent Mosley: 100 percent.

Jaclyn Van: It's horrible if you have to feel like you're asking something that someone's likely said many times before. And fortunately at Drift, and Trent, especially, I've never really felt that way. It's nice to come in feeling really informed, and I think the customer certainly appreciates that as well.

Sammi Reinstein: Yeah. And Trent, I mean, compliment from JV, legendary notes, legendary in the CS org. That's amazing.

Trent Mosley: She's the rockstar.

Sammi Reinstein: Yeah. Well, you're both rockstars.

Jaclyn Van: Read his notes, everybody. They're great. They are great.

Sammi Reinstein: So Trent, how are you thinking about, in the sales process, what it looks like once you sign that customer and pass it off to someone like Jaclyn? Are there any tips you have for people in terms of thinking about the long- term health of the customer?

Trent Mosley: Yeah, that's a great question. I mean, for me, I think it starts very early on. And I actually phrase it in my evaluation for the customer. Whenever we're going really deep into things, I always call, like," Hey, I just want to make sure we're aligned here for actually implementation, your onboarding team." I might be digging deep into these questions, but it's not more so for my sake of," Oh, more discovery questions." No, I want genuine alignment for the business. So post- sale, we actually stick to our word on what we say we're going to deliver. That's the most important thing to me, is making sure my name, my brand, my integrity is attached to everything. And that's why I go so deep into the notes for Jaclyn, the CS org. I'm like," Okay, I don't want to slip up here any point on alignment on what we said we're going to promise, what we're going to deliver, who is involved. So let me just give them everything and anything that they need ahead of that kickoff call so we don't have any mishap alignment." Like I said, it starts early on in discovery, understanding the business problems, the key stakeholders, what we're looking to accomplish, timeline to go live, setting the proper expectations there and carrying that over, not only from the beginning to the end, but post- sale as well to the team internally on everything that was discussed months in advance.

Sammi Reinstein: Yeah. And I'm sure that's great for JV to go back to in Gong and just look up alignment in your calls, and then they'll be able to see everything that you've talked about with the customer too.

Trent Mosley: Oh yeah. For sure.

Jaclyn Van: Oh yeah. Alignment, goals, KPIs, all of those search terms, really, really helpful. And then I think it's true because people are so excited, I think, when they close with Drift and when they get on that kickoff call. And Sammi, you mentioned this earlier, too, that first impression on the customer org side is so crucial because we want to keep all that positive momentum going forward. So that's something with that added context, it just makes it so much easier to be able to execute on that.

Sammi Reinstein: And so you've both been here almost three years, or maybe more than three years, which is great. So I'm sure you have seen Drift and the sales and CS relationship change over these past three years. Jaclyn, can you start us off in just walking us through how that's changed, and what are some mistakes that happened when you first joined that you've now sort of remedied?

Jaclyn Van: Sure. So it's changed quite a bit over my time at Drift, so just over three years. It started out when we would typically work directly with the AE who closed the opportunity. And at that time, there were different types of plans at Drift, different size customers that we were working with. We've since segmented a bit. So I think just due to the more variety, I guess, and more people involved, that got a little bit more challenging. Because I think it all comes down to communication and being able to have those clear conversations around, this is the customer, this is what's most important, this is what you might want to ask about or double down on. And move forward. So we didn't always do, I think, a great job of that, but it's gotten so much easier over the years. And I think in terms of mistakes that we've overcome, I had one instance on a call where a customer, when I'm talking about something that was really exciting, it was ABM, it was inaudible list targeting, and they were loving everything I was saying. And then we left the call, and then the AE was like," Oh, well, they didn't get that plan." And it was like," Oh my gosh, that's so embarrassing." So he had to jump in, and he owned that conversation, which was good. And they eventually upgraded, which is nice, because hopefully I sold them a little bit on the first call. But I just felt so bad. I was like," Oh, that's so awkward to set that false expectation," which you can really avoid just by having clear notes like Trent's, or just by having those things ahead of the kickoff and really post kickoff as well.

Sammi Reinstein: Yeah. And Trent, from your perspective, how have you changed the way that you have communicated what happened in the sales process to the CSM?

Trent Mosley: Yeah, no, I would think back to my first week at Drift and my first ever deal. Jaclyn referenced my notes. I remember that first week I was still sending very in- depth notes like that because I was traumatized from a past company of customers churning and always feeling like," Oh my God, this is my fault. I didn't set the proper expectations. I didn't communicate well enough for my onboarding team," and just really owning that. And I think that's what resonated over when I started here at drift. I was like," Okay, no longer will that ever happen. I don't want to put my customers in a bad spot. I don't want to put anyone internally in a bad spot." And I think it's funny because that has grown so much. Before, early days at Drift, it'd be account manager and a CSM. Now we have playbook optimization special, professional service engineers, CSM, onboarding manager, all these different people, yet we still have to make sure that alignment's there. So it's, okay, now it's playing project manager internally to make sure we do everything that's right for the customer, setting those proper expectations. And although it has changed from the early days, more so about the amount of people we're working with, the process has still remained the same, making sure early on sending those in- depth notes, making sure we have alignment, and across the board, making sure everyone's on the same page. And it's funny enough, before we didn't have these pre- kickoff conversations. Now I don't sign a customer where I send the in- depth notes, and we still internally sync before that kickoff call to really make sure that we're aligning. And I don't think there's any other way to paint a better cohesive customer story than making sure we have that alignment.

Sammi Reinstein: Yeah. Alignment and setting proper expectations. From just everyday life, I think we can all agree that there is just nothing worse than having expectations that were set totally improperly. It goes down to so many business experiences, too, that I have had, that I know so many people, just in their general day to day life, whether it's business to consumer or B2B that they've had. And we talk a lot on this podcast and just generally at Drift about customer experience and making the best customer experience possible. And I'm curious, Trent, in your sales process, how are you thinking about creating a really conversational and good customer experience?

Trent Mosley: Really? I mean, it's funny, you hit on it right there. The biggest thing about customer experience to me is communication and setting the proper expectations. And thing about that is, if I reach out to you, it's okay if you don't get back to me. I think of it from my inaudible. I'm reaching out to a vendor and I have a question. If you don't get back to me instantly, that is fine. I get it. Everyone's busy. People have different jobs. I have a job, I have a life, I have a family, I have a puppy. I'm busy. But communicate with me that you will not be getting back to me instantly. Set the proper expectations. If I'm not going to get back to you in 24 hours, I'll get back to you in 48 hours. Or even better than that, and get back to me instantly. So I think the communication and expectation setting is the biggest thing about customer experience. Across the board, when working with different vendors, businesses, B2C, but not only that, relationships, the experiences you have with people, it's all about communication and expectation setting.

Sammi Reinstein: Yeah. And we're lucky at Drift, too, where we get to eat our own dog food, where we have our Drift bots where someone's not available, we get to drop the calendars and have automation take care of it. And I love what you said about relationships and really focusing on relationships. And I'm curious, Jaclyn, from a customer success side of things, how do you foster those relationships and continue that great customer experience once Trent has signed that customer, emojis have flown through Slack, and then you get to work with them?

Jaclyn Van: Oh, I love that piece on relationships because that's the best part of the job, working cross- functionally, internally, and with your own team. And then also, we get to work with some really great customers too. So I think what I've seen, of course it's nice. And what we really drive towards on the success side is showing ROI. So through the playbook strategy, we're going to make sure that we're advising people per best practices to get the most out of their Drift investment so they can kind of continue to grow with Drift over time and see more value over time. And that said, there are, of course, going to be some hiccups along the way. There could be a bug impacting their account. There could be other stuff going on. And I think it's just showing that whether they're chatting with support, they're on a call with their CSM or onboarding specialist, they're on a call with Trent post- sale and he's checking in on how things are going, that we're just showing that across the Drift team, we're a united front to put the customer at the center of everything and really just do whatever we can in our power to give them a better experience. So I think that ongoing commitment really resonates with our customers. I think they see that human side of it. And I think that's really what's helped our customers really trust us and us to be able to trust them too. And then what I love too is when we do show success, and some people even get promoted just due to the work that they've put into Drift and what Drift has been able to drive to the broader org, that's the most validating thing I've seen

Sammi Reinstein: That is absolutely the best, when you see your point of contact get promoted. What an amazing feeling. You've helped in so many ways, not only business and increasing pipeline, but also that individual growth of that person.

Jaclyn Van: It is awesome. And it's all the customer too. I mean, it's them kind of working with Trent to get the deal across and kind of sell that internally, and then showing that commitment as we get on onboarding calls and beyond to keep doing things with Drift and not setting anything and forgetting about it. So definitely that continuous effort has been great to see from our customers.

Sammi Reinstein: Yeah. A unified front. That is definitely what I'm going to take away from this and that, like you said, Jaclyn, it goes sales, CS, our support, our professional services team, everyone, making sure that they're fostering that relationship and putting the customer first, putting the buyer first. Speaking of unified front, what are some big hurdles that you feel like the sales and CS relationship, just in general, has to overcome? Trent, I'm going to pass this one over to you first.

Trent Mosley: Yeah. In thinking of it, I think the biggest hurdle starts with one of the main topics we've been talking about is communication and expectation setting. I think there's the stigma that sales people just try to sell anything or tell a customer whatever they want to hear, but at the end of the day, it's not like this is a sell it, here you go, I'll never talk to that customer again. And I think that's the biggest problem there is, it's having that alignment and making sure that communication is there. The hardest hurdle to overcome is making sure you don't lapse in that communication and that relationship you have. Communicate everything. If you messed up and owned it and didn't mention something or told the prospect something that you found out wasn't correct or accurate, maybe it's not in beta, you need to let your team internally know this as well so they don't fall on their face and they're setting the proper expectations." Hey Mr. And Mrs. Customer, I messed up. You're right. We were in beta. We're no longer admitting this to the general public. That is on me. Jaclyn, team, I let them know we were doing this. We are no longer doing this." It's all about the communication. It's so funny because like it's so simple, yet it's one of those things I feel like so many people struggle with. Not just at Drift, any sales person, I feel like it's one of the biggest hurdles is making sure they have that great alignment with their team internally and they're communicating enough. And I laugh because sometimes I wonder," What does this onboarding team think of me?" Because I'm constantly pinging them before calls, after calls, during calls, post sale, everything. Jaclyn knows. I'm always pinging them, but I'd rather over communicate and make sure I do overcome that hurdle to make sure we're aligned for the needs of the customer versus under communicate, you never hear from me, I sell it and don't even Slack you to say, "I'm excited to work with you." It's all about the communication aspect. And I think that's the biggest hurdle we as salespeople and CS teams and post sale need to overcome to have that alignment together.

Sammi Reinstein: Yeah. So what I'm hearing is ownership.

Trent Mosley: Yep.

Sammi Reinstein: Over communication.

Trent Mosley: Oh yeah.

Sammi Reinstein: And then that will all lead to that unified front.

Trent Mosley: Hundred percent. Hundred percent. Spot on.

Sammi Reinstein: And JV, from your perspective, what do you feel, just in general, from a sales and CS relationship, what do you feel like the biggest obstacle is that you face just being in CS?

Jaclyn Van: Sure. I mean, I think it's kind of along the same lines of communication, and I would even take a step of saying that's any jobs, out in tech industry, outside of SAS. That's anywhere. So I think it's really easy if you get notes that you're not satisfied with to kind of complain in your head, keep it internally, and be like," Oh, they didn't do anything, or they didn't document anything" and keep it to yourself, but then you're doing a disservice to yourself because you're going to have to ask all of that of the customer, and to the customer too. And then I think especially if someone is potentially is new or they didn't know that that's the process that we have, or they hadn't seen Trent's amazing examples of notes in the past, like there's a great coaching opportunities cross- functionally too. So I think being able to kind of empower yourself to say," Hey, do you have an answer to this question? If not, just let me know, and we can double down on that on the kickoff or after that call." So I think that taking those extra stress steps is helpful. And it can be hard sometimes to feel like," Oh, I'm just badgering somebody about a deal they closed a month ago. I'm asking all these questions." But I think as long as you're communicating why you're doing it, it's really on behalf of the customer, and why it's so important, it's so we can be aligned and move forward as that united front, then I think that can be really effective.

Sammi Reinstein: Yeah. I love that. We, the name of this podcast is Conversation Starters. And when we think about conversation starters, a lot of the times we're thinking about sparking those conversations with customers, starting those conversations with fires. But internally, having those communication and those conversations between each other is so key to create those other conversations with your buyers and your customers.

Trent Mosley: Just as important, if not more important.

Sammi Reinstein: Jaclyn and Trent, thank you so much for coming on the podcast. I've learned a lot, and I'm also very inspired by the relationship and communication that the two of you have. And hopefully everyone listening to this will over communicate and continue to have those conversations internally. So thank you so much.

Trent Mosley: Sammi, Jaclyn, thank you. It's a pleasure. Jaclyn, I'll be slacking about our EBR for our customer coming up in a little bit.

Jaclyn Van: Coming up. No, that sounds good, Trent. Thanks so much, Sammi. Really appreciate it.

Sammi Reinstein: Thanks.

Trent Mosley: Thanks, Sammi.

Sammi Reinstein: Wow. I love the JV and Trent dynamic. They're just both two truly wonderful human beings, and I loved hearing them talk too.

Elizabeth: I love hearing them talk and I love how much they celebrated each other and each other's work. And I think that's very important in a sales and customer success dynamic.

Sammi Reinstein: Yes, it was very much like Oprah. You get a compliment, you get a compliment, back and forth. That was like we're playing ping pong here. But I loved it, and I loved the focus on over communication because that's definitely something thing I lean into, and Trent and all his notes. I also think it's important to have notes versus just a conversation because I write everything down, so Trent seems to be catering to every aspect that can make a CSM successful.

Elizabeth: A lot of what we talked about today is also very relatable to any cross- functional dynamic and relationship, having strong communication, having a unified front, and taking ownership, which is one of our core principles at Drift and is just so helpful in any relationship.

Sammi Reinstein: Yes, I agree. I think it can be seen throughout the entire company, and we'll probably hear about it next week when we actually have a special episode featuring product marketing at Drift.

Elizabeth: I am so excited for that. We're going to have Aurelia Solomon on, who is our Director of Product Marketing. She is so knowledgeable and really a master in her craft. I can't wait, so make sure to tune in.

Sammi Reinstein: Thanks so much for listening to Conversation Starters. If you liked this episode, please leave us a six- star review by clicking the link in the show notes. And hit subscribe so you never miss another one. You can connect with me on Twitter at Sammi Reinstein and follow all of our shows at Drift Podcasts.

DESCRIPTION

On this show, you've learned how to leverage conversations to build brand awareness and to book a meeting. But what about after the customer signs?

Once that contract gets submitted, the conversation is really just getting started, and Drift's enterprise account executive, Trent Mosely, and enterprise customer success manager, Jaclyn Van, know this best.

So in the spirit of Valentine's Day, we're highlighting the sales and customer success relationship. Drift's Trent and Jaclyn (fondly known as JV) join Sammi to talk all about how they work together to create a seamless customer experience that never misses a beat. Hear how Trent uses emojis to show his appreciation, why every sales message should be written with the long-term health of the customer in mind, and some of the biggest mistakes Trent and JV have made -- and how they've fixed them.

  • (5:00) How Trent & Jaclyn work together
  • (7:35) What the sales --> customer success handoff looks like at Drift
  • (9:36) How Trent & Jaclyn think about the long-term health of the customer
  • (12:04) The mistakes Trent and Jaclyn have made over the years, and how they've fixed them
  • (16:01) What a good, conversational customer experience looks like for Trent
  • (17:38) Jaclyn's favorite part of her job
  • (19:55) How sales and customer success can create a unified front

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