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Episode 26: Customer success management 101: The value of relationships

Sippin' & Shippin'
Sippin' & Shippin'
Episode 26: Customer success management 101: The value of relationships

Tanya Phipps|October 28th, 2022

Happy customers are the life source of thriving brands. But ‘customer success’ is so much more than just making customers happy. It means ensuring customers are getting their needs and expectations met at every level, including how you support and act on their behalf. We sat down with Leslie Karr, Director of Customer Success at Ryder E-commerce by Whiplash, for a deep dive into what an effective customer success management process looks like, and how brands can pioneer a similar strategy.


03:20 What is customer success? 

04:49 Managing CS relationships: Partner, communicate, collaborate

06:39 Partner: Establishing a connection and understanding the ‘big picture’

08:56 Communicate: Setting expectations and welcoming feedback   

10:48 Collaboration: Bringing your partners together 

12:07 How to bring partners together 

15:15 The value of customer success in e-commerce 

19:28 Who are customer success managers?

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Brian Weinstein: Welcome everybody to Sipping and Shipping. I’m your host, Brian Weinstein. We’ll be kicking it here every other Friday quenching your thirst for an insider’s take to enhance your customer experience. So grab your drink of choice, kick back, it’s Sipping and Shipping time. All right, welcome back everybody to another episode of sipping and shipping. I’m your host, Brian Weinstein, and I’m here as I am every week with Caitlin Postel.

Caitlin Postel: Hey, Brian. Every other week, right?

Brian Weinstein: Every other, well, I’m with you most every day.

Caitlin Postel: Well, unfortunately for you, every day.

Brian Weinstein: Yes, exactly.

Caitlin Postel: Exactly, unfortunately.

Brian Weinstein: Yeah. So it’s not every week, but we are not every week for the show, but almost every day for life.

Caitlin Postel: Well, every day we’re sipping and chipping.

Brian Weinstein: Exactly right.

Caitlin Postel: Maintaining the name.

Brian Weinstein: In this week we have one of our very own Leslie Karr who runs our customer success group. Welcome, Leslie.

Leslie Karr: Thank you so much. I feel privileged to be on Sipping and Shipping.

Brian Weinstein: Yes. Do you feel a little bit of a complex because you don’t have the big microphone and all that stuff?

Leslie Karr: Yeah, because I feel like that would make me really official and that would be nice. I’m looking at you, too, and I think it’s a good look. It’s like the real deal, right?

Caitlin Postel: Don’t let him fool you, Leslie. Don’t let him fool you.

Brian Weinstein: And it hides half my face, which is perfect. So if I can only duck down so that you can’t even see the bags under my eyes, it’d be perfect. All right, so this week we are talking about customer success. Leslie, tell us a little bit about your background. I mean, it’s most of your career, correct?

Leslie Karr: Yeah, yeah. Twenty plus going on 25 years in the customer success, service, and support realm. A lot of what I have done has been in software as a service related to industries, so email marketing was a large part of my career, as well as social media marketing, hotel hospitality, sales enablement, and market research have been all the types of companies I’ve been involved with, all software service related. This opportunity here at Ryder E-commerce by Whiplash has been my first foray into the 3PL space, but it brings in that software as a service component big time with the Whiplash application. I feel really, really at home here, and I’m learning and have learned so much about the 3PL industry.

Brian Weinstein: Once you get sucked into this whole fulfillment logistics space, it’s like an addiction. You just can’t give it up, because life after that just seems so easy and simple, and who wants easy and simple?

Caitlin Postel: I’m four years in, and I don’t think there’s an exit strategy yet. So yeah, I’ll attest to that.

Leslie Karr: Yeah. Well, it’s exciting because of the complexity and of what the ultimate deliverable is in our industry. Because really in the e-commerce, third party fulfillment, it really hits home. You’re like, “Oh yeah, I want to order from that cool digitally native brand, and I want to get that delivered right to my doorstep.” It’s very relatable, so I’m loving that part.

Brian Weinstein: Yep, absolutely. So tell us a little bit, what is customer success?

Leslie Karr: Customer success is when a customer of yours is getting all of their needs met, their expectations and needs met by everything that goes on within your organization, and then how you support them and act on behalf of them and get the job done. That’s what customer success is in a nutshell.

Brian Weinstein: We’re speaking today specifically more about a B2B type of customer success, right?

Leslie Karr: Yeah.

Brian Weinstein: This isn’t your call center type of, right?

Leslie Karr: Right. Customer success is very common to have that discipline within business to business organizations. So when your customers are other businesses, they want to make sure that they’re getting the value out of your relationship. That means you have a customer success organization that tries to ensure that. Anticipates the needs, knows what the needs of that customer is, that business customer. And different than support. Customer support is more, “I have a question, can you help me with this problem?” It’s a little more reactionary. It’s like, “Here’s a question, we’ll get you an answer.” If customer success and customer success management is proactive, strategic, I can see down the line that my customer’s going to need something, and I try and fulfill it and coordinate internally to make that happen. That’s the difference.

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Brian Weinstein: What are some of the keys, I guess, to initially establishing yourself with your customer, and what that role looks like?

Leslie Karr: When I think about the e-commerce brands that we work with, they have a lot of different companies in their tech stack, a lot of different partners, a lot of different vendors. That’s a lot to kind of manage for a brand. Oftentimes they could be really small teams, one or two people, up to even the larger companies that have a number of people working in a relationship with a vendor or a partner. It can be daunting for a brand to figure out how to manage those relationships.

I always think about it in with three categories of things to keep in mind: partner, communicate, and collaborate. If you’re the e-commerce brand and you’re bringing on a new vendor, you want to first set expectations that you want to partner with them. The customer success side of that organization should really perk up when you say things like that, because they’re really looking for that. It’s not just a vendor, not just doing X, Y, Z each month and sending you an invoice and it’s done. This is a partnership. It’s a complex situation in terms of e-commerce brands. Tech stack and other people they’re working with, you should be partnering with your vendors, not treating them like vendors, if that makes sense.

Brian Weinstein: Yes.

Caitlin Postel: Yeah, I think that makes a lot of sense. I know in the sales process, that’s typically a question that brands will ask, “Will I have a direct contact? What does that look like?” And when I say, “Customer success,” I think the ears kind of perk up. But what does that look like? How do you define that partnership? And how does this person become, to your point, more proactive versus reactive?

Leslie Karr: Yeah. In that partnership, you want to start out by setting expectations. How will you work together? How will you work with your CSM and the other folks at the organization? You want to also share the context of your brand and the bigger picture so that the customer success manager on the other side understands higher level what you’re really driving at, business goals, that type of thing. Obviously you’re going to share certain key KPIs and performance metrics, but what do they mean and what’s the bigger picture backdrop of what your company is trying to achieve?

Brian Weinstein: I always look at the whole partner concept, and I could speak specifically to 3PL, right? It wasn’t like that before they had a traditional customer service rep who was a little bit more day to day tactical. It wasn’t going out of your way. And I’m certainly not saying by any means that we’re the only ones that do this, but I think it’s something in the 3PL space that is relatively new, is just really getting in there and having that partner. Being a partner with your partner as opposed to the way it was before.

Leslie Karr: Yeah, I think we were talking earlier about how there’s the software as a service component, the Whiplash application for instance. And then there’s the actual operations in the warehouse facility. That’s a very complex ecosystem, and there’s a lot going on between operations, technology, engineering. The customer success management function is supposed to help all of that work together better for the customer, and understanding the customer’s most important needs there, and applying to all of that complexity. That’s really where the customer success management function can shine.

Caitlin Postel: I love that concept of the upfront contract of just understanding the bigger picture, what is there, why, and what is their expectation of what they’re going to get out of this relationship? Which I think helps to transition from turning it from, “You’re my vendor, I’m your customer,” into, “We’re partners, how are we going to tackle these initiatives together?” Which I love.

Leslie Karr: Yeah. We can even get into the brass tacks of the communication piece that I mentioned. This is where you can really bring that partnership to life. What are the communication methods that are going to work best for your team in speaking with your partner now? What are the regular meeting cadences that you can have where you’re touching base on a strategic level? Maybe operationally strategic, maybe it has something to do with technology, but when you are having those regular meetings? It also gives you the opportunity to talk about how to do feedback. Because if you set up those communication methods and those meetings, then you want to make sure you’re providing positive feedback and constructive feedback to your customer success manager that improves that whole partnership overall.

Brian Weinstein: Yeah, I think that communication is two way, especially when the partner and the customer success manager that you have is that true partner and there’s trust. Because I think trust is one of those things that has to be built right out of the gate. You can provide both positive and constructive criticism in both directions for the sake of bettering the experience.

Leslie Karr: Absolutely. And that’s why you give a bigger context to what you’re trying to do that allows the customer success manager to be more preemptive of like, “Oh, I see what’s going to be happening. Let’s make sure we’re all on the same page, operations.” And that builds trust, too. The more information you give your customer success manager, they can wow you by thinking ahead even further than you are, and that’s [inaudible 00:10:44].

Caitlin Postel: Dazzle and delight.

Brian Weinstein: Exactly right.

Leslie Karr: My last of the three is collaborate. If you treat them like a partner, you set up your communication, then this opens up collaboration, like true collaboration. As an e-commerce brand, I always recommend that you bring your related partners together, so your 3PL and your returns provider or what have you, any of that. Introduce them to each other, set some expectation. Maybe it’s quarterly that you want to have some sort of communication or touch base. Maybe that’s an important priority. Go ahead and do that. You want these folks working together on your behalf, so introduce them to each other and encourage communication on appropriate topics.

That also sets you up for when there’s challenges. Because this complex systems that we work in and things can go wrong here or there, you want to work with your customer success managers to collaborate on overcoming the challenges. Work together, bring in the other partners. “Hey, what do we need to do to collectively? If we do this over here, can you do this over here?” That really makes when challenges come up, they can get resolved much more quickly if everyone pitches in to help and they’re in that collaboration zone.

Caitlin Postel: So Leslie, what does collaboration look like as far as bringing those partners together? You talked about before setting up. And it’s so simple, but such a great concept of how are we going to communicate, what does that cadence look like? At what point does it make sense, or how do brands approach bringing other vendors together? What have you seen is the most successful way of attacking that?

Leslie Karr: The good news is that there’s not one pat answer, and it can really depend on what the e-commerce brand’s needs are. You don’t have to get fancy, you don’t have to set up yet another regular meeting. You can simply do a introduction and a quick expectation setting between the vendors that says, “Hey, I’d like to touch base.” Maybe it’s quarterly if you do want to set up a meeting, or maybe it’s initially. “Let’s set up just an initial meeting.” And then from there you can take the coordination and collaboration into email. Or when a situation arises, you can call up the troops so to speak. But you don’t have to make it onerous to set up this collaboration between partners. I think it’s key you just set the expectation up front by introducing them and saying, “When things like this happen, I’d like us all to work together. I’d like you to work together on those kinds of topics.”

I think that’s super powerful for your various partners to hear from you, because they’ll want to include you, they’ll want to take that initiative and be like, “Hey, you introduced me to so and so, I’d like to bring them into this.” And they can be suggesting when it’s time to bring partners together. You don’t always have to be the person saying, “It’s time for us to get together.”

Caitlin Postel: That makes sense. It’s not a one size fits all, but at least if you’re empowering them to work together, why not stack up those resources? Let them remove the middleman, let them communicate to continue to leverage those resources to work towards that big picture “why” which keeps coming up. Why are we here? What are we trying to achieve? The more you know, the better they can work together. Yeah, understood.

Brian Weinstein: I think as things have gotten much more complex, right? There’s so many more layers in a lot of the fields, certainly in our 3PL space. Where there may have been more of a cloak of secrecy almost years and years ago, it’s become, “Let’s forge an even broader net of collaboration with all of the resources coming together.”

Leslie Karr: Absolutely.

Brian Weinstein: Which is interesting.

Leslie Karr: Well, that’s what I’ve learned in the software as a service business. There’s so many integration points that you can have within your tech stack. You want to be able to utilize the expertise of all of those folks in that tech stack. There’s a lot of intertwined best practice, or tips, or, “What do other people do, what do other brands do in this situation?” You want to pool that knowledge and apply it to your situation. It unlocks a lot of power for you as an e-commerce brand to bring those folks together.

Brian Weinstein: What would you consider some of the biggest values that having a strong customer success team at your disposal brings to a brand or a product or service or whatever?

Leslie Karr: Well, first and foremost, they will be looking at your needs. They’ll be analyzing what you’re telling them is important, what the priorities are. They’re going to be looking at that as, “Well, these are needs.” And as experts within their world, whether in our environment be the Whiplash application and how we apply that in our operations, they will be able to bring to bear that on your needs because they’re understanding your bigger picture.

Secondly is they will be coordinating internally, because they will be acting as you, but internally within. Again, you’ve got the software, the technology, you’ve got the operations, you’ve got small parcel, you’ve got all of these things going on at one time, and the customer success manager will be a central hub. They’re not like your most important person on your team within; we’ve got operators who do all the key work all every day that that’s so critically important, but they’ll have a worldwide view of your activities and needs within our company. And that’s really powerful.

Brian Weinstein: It’s a role that really makes sure that there’s strong alignment on the internal and external side. I mean, it’s such a critical, and again, going back to things are more complex, there’s more touch points. Everyone needs to be aligned.

Leslie Karr: Right, right. It’s a big job, but the customer success manager sort of mandate is to help internally and help externally. It’s a help everywhere to make the needs come to fruition for the customer. That is something that you’re not necessarily going to get through just a support channel, because that’s more reactive. That’s more, “I have a question, I have an issue.” The customer success manager is really trying to be more proactive for you and look ahead.

Caitlin Postel: We’ve talked a lot about ways that you could leverage your brand success manager or things that you should go to them on. Where do you draw the line? Where is it like, “No, the customer success manager, they’re not the right person for that.” Where do you see brands stepping outside of the boundaries?

Leslie Karr: I have to say that by and large, in my experience, brands don’t do that. If we do a good job of setting out the expectation of what a customer success manager is and where they can get support and how they should get support, whether it’s through a customer success manager or through maybe more of a ticketing support team or something like that, then a lot of brands, they get their needs met. So they don’t to feel the need to say, “Well, okay, can you just do this for me?” if it’s not quite appropriate. So by and large, if we do our job in laying out and executing on that, how we should support them, that doesn’t happen very much.

Caitlin Postel: But it’s advantageous for them to stay in their lane, right?

Leslie Karr: Yeah.

Caitlin Postel: It’s like, “Let them keep focusing on what they’re doing. Let’s not distract them.”

Leslie Karr: Yeah. But when it does happen, honesty and transparency is the best policy. It’s, “Hey, this ask, we’re going to be able to accommodate it, but let me help you figure out how you could can do it.” And obviously there’s things they could bring from their other customers in how they approach that situation. There’s their knowledge of your operation because you’ve treated them like a partner and you’ve given them insight into your culture and how you work, and they might be able to recommend things. And so we never want to just be a hard no, but we want to support, “Hey, this is what we can recommend.” And so ideally through some transparent discussion, you could still help. We can, as a customer success team, can still help the customer get their need met.

Brian Weinstein: Individuals. Like, what kind of individual are you looking for for your team? Because it sounds like they have to be able to cover a lot of different aspects and understand a lot of different aspects.

Leslie Karr: Customer success managers sometimes are really a rare breed, but the first thing is that they have the customer gene. They feel, they think like a customer, they understand a customer, they’ve worked in customer support, service, or success before, and they have that innate understanding of what it means to think like the customer and support them. So that’s really important.

In the 3PL business, and particularly something like the Ryder E-commerce space, it’s having a technical knowledge, being able to understand software and how it works in the 3PL world, and having a little experience in the actual fulfillment and operations side. Those are sort of three big aspects, is customer, technology, and ops and fulfillment knowledge. Those are the three big areas that I look for.

Brian Weinstein: Well, you’ve built a great team, and you’ve got a lot of great people there. And I’m saying that at the risk of being considered a shameless plug, but I do have to say that.

Leslie Karr: Well, our team is wonderful. I’m really grateful that I have such wonderful people on my team. We’re growing and evolving. We’ve added new team members. And we’ve also been just looking at everything we do. We always want to get better, so look for us to do more in the future.

Brian Weinstein: That’s awesome. Well, Leslie, thank you very much for coming on and talking about customer success, which for me has been a breath of fresh air for our organization overall. And I think the benefits, whether you’re a 3PL or in a SaaS space and a multitude of other industries, having that right customer success could differentiate you from others.

Leslie Karr: Well, thanks for having me. It’s been great.

Brian Weinstein: All right. Caitlin, you want to take us out?

Caitlin Postel: Yeah, sure. Thank you, Leslie, for joining us. Thank you to you and your team. Our customer’s success is ultimately our success, so appreciate everything you guys do. Thank you everyone for tuning in to another episode of Sipping and Shipping. We’ll see you in two weeks. Check us out on your favorite podcast platform. Thanks, everybody.

Brian Weinstein: Thanks. All right. Awesome.

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