Kailey Killoran: 0:03

No matter what goes wrong, it's impossible to get a hold of someone, and that's very much not what we want to be providing to customers. We want to have a very open door so the customers can engage with us at any point in the journey.

Alex Turkovic: 0:15

And that is easier said than done, for sure.

Kailey Killoran: 0:20

Yeah, sounds great in theory. Definitely harder to execute on in reality.

Alex Turkovic: 0:25

And, once again, welcome to the Digital Customer Success Podcast with me, alex Turgovich. So glad you could join us here today and every week as I seek out and interview leaders and practitioners who are innovating and building great scaled CS programs. My goal is to share what I've learned and to bring you along with me for the ride so that you get the insights that you need to build and evolve your own digital CS program. If you'd like more info, want to get in touch or sign up for the latest updates, go to DigitalCustomerSuccesscom and if you have a question or commentary to be used in an upcoming episode, call us and leave a message at 512-222-7381. For now, let's get started and welcome to episode 18 of the Digital Customer Success Podcast. I'm so grateful that you are back and for those of you who are new to the show, welcome Glad to have you here. One quick reminder before we jump into things is something that I've mentioned before on the show and actually comes up in the conversation today, but that's the DCS Connect community. It's a Slack community, relatively new, started by Marie Loney, where we talk about all things digital customer success. There's a ton of best practice sharing in there. So if you're new to digital CS if you're actively involved in it or just curious about it. There's a link in the description to get access to that Slack community. Go join it.

Alex Turkovic: 1:51

For today I am so pleased to have Kaylee Killeren on the podcast, who is director of customer success and digital engagement at Lupio. Kaylee and I started talking quite a while ago I want to say maybe a year ago or so and one of the unique aspects of this conversation is that you'll get to see and hear from somebody who's in the throes of building up a digital program, because it wasn't too long ago where she was tasked with okay, how do we tackle this whole digital customer success thing, and she's done a really phenomenal job of doing that. So you'll kind of get to ride along and listen to some phenomenal insights, some lessons learned and sort of really smart and engaging individual talking about digital and just it's an episode that's just jam packed with great information. So I hope you enjoy this conversation with Kaylee Killeren. I know I sure did. We have been chatting for, I guess, a few months now, because our companies are. What is it called when you're in the same portfolio? Are we sister companies? What is that?

Kailey Killoran: 3:01

It's a kind of familial relationship, I'm sure.

Alex Turkovic: 3:05

Yeah, exactly, but we've been chatting for a while because we're obviously CS leaders at adjacent companies and talking about rapping about digital, and I was like we need to have you on the podcast and chat about what you're doing in digital, because one of the reasons I'm excited to have you on is because we don't we haven't talked to, first off, we haven't talked to a lot of Canadians so there's that and but we also haven't talked to a lot of people who are in the process of kind of getting the ball rolling in terms of digital and being in the weeds of that, and I know that's been hot and heavy for you. So, kaylee, that was a super long intro, but welcome to the podcast and I'd love, before we get into, like, all the exciting stuff that you're doing, I'd love for you to give us a little bit of taste of who you are, what led you to CS and what keeps you in CS.

Kailey Killoran: 3:59

Yeah, for sure. Well, thank you so much for having me. I'm excited to chat today and, yeah, we are doing it totally differently up here in Canada, so I'm sure we'll have lots to dive into.

Alex Turkovic: 4:08

Lots of maple syrup A key part of our digital success program.

Kailey Killoran: 4:15

But yeah, so I'm the director of customer success and now digital engagement at Lupio and I have kind of started my career in sales, had started in sort of business development, moved into essentially an AE role and then started managing sales teams and then moved over into account management and then eventually customer success. And I would say my specific journey into customer success was, you know, really when I made this move from account management to CS. I really started to try and unpack what are the differences and how do you think about a customer success team differently from an account management team? And I really have this sort of light bulb moment around how much the maturity of your product plays into what the customer success function means at any given business. And so at the time I was at a company where we were going through this transition and sort of evolution of our product where we really required CSMs to fill less of a gap in the product than they were previously.

Kailey Killoran: 5:20

And so that was kind of my introduction into how do you define a CS role and what does that mean, and what does it mean for a very early stage startup versus a scale up etc. And how does your sort of product maturity play into that. And then at Loupio, when I joined the team, I was working more so with our mid market CSMs and then became more focused on our SMB segment over the last I guess about 18 months and naturally a big part of that has been digital customer success and CS at scale. And even over the last few months we've continued to grow that function within the business and really started to revise how we think about digital CS and CS at scale. So I'm sure lots for us to dive into today.

Alex Turkovic: 6:03

Yeah, absolutely. A little bit more about your background too, because I think, if I read correctly, you were a polysine major undergrad and graduate. Right, yeah, and where did that? Like, I am the epitome of somebody who doesn't use my degree.

Kailey Killoran: 6:23

All right.

Alex Turkovic: 6:24

I got a, I got an arts degree in music, right, so whatever. But talk to me a little bit about that, because that's a whole different world. And do you utilize those skills? I would imagine you use them, probably daily, but yeah, it's always.

Kailey Killoran: 6:41

What is that? It's funny. I think people have a very different experience of you know. Getting an arts degree or a polysine I think very much falls into that same bucket of you know degrees that people wonder what the eventual use is. I think for me I didn't necessarily have the expectation in going into my undergraduate or or my graduate degree that I was doing this to get a specific job or because I thought it was the degree that was best set up to support me in the workforce. This is going to sound really nerdy, but I just love learning Like. I am really an academic at heart and I love politics. I love political philosophy, I love the overlap of that with law, and so I never really looked necessarily at my degrees as anything more than just the amazing opportunity to study and spend time on something that I really, really love.

Kailey Killoran: 7:38

But to your question about how I use it in my career now, I think actually the sort of special skill that it's given me in in business and in leadership is the ability to distill what is really happening in a conversation.

Kailey Killoran: 7:55

So so much of a any arts degree, and particularly politics or political theory, which is really what I sort of specialized in is critically analyzing an argument and understanding you know what the other side of that argument is, what the weaknesses of your own argument is, and so much of what I feel like I'm able to do in conversations now in a business setting is here, here to people talking about the same topic and be able to quickly identify what they're really trying to talk about, that they might be missing, and to sort of distill the conversation down to say I know you think the conversation is about this and you think the conversation is about this, but really the the root of the problem that you're trying to solve is this. So let's make sure we're at least having a conversation about the same thing and go from there.

Alex Turkovic: 8:46

That's so valuable. Wow, I mean, as you're talking about it to me, the word or the phrase that comes to mind is emotional intelligence, like hyper emotional intelligence. Like you, you can put yourself in the shoes of the of the people talking in the room and see the different sides and and then know how to like integrate with that right.

Kailey Killoran: 9:08

Yeah, it's funny you say that, because I think that's so much of what we talk about when we talk about CS in general. Is you know that self awareness or emotional intelligence? Of course you need to know a product, of course you need to understand some of the business fundamentals around that, but you also need to be able to connect with people and have the awareness of how you're showing up in that conversation, and so I feel like that's so much of what we talk about when we talk about even you know growth plans or you know how folks evolve in a CS role. So much of it comes back to that same theme.

Alex Turkovic: 9:41

Yeah, absolutely Also related to your background. It seems that you you obviously started in a sales capacity but you ascended to leadership quite quickly In your career and I'm curious if that was a conscious like a goal, like a conscious decision where you just a bad ass and you know got promoted quickly. Was it a combo of both and and and? If you're anything like me, like leadership is just kind of part of your DNA, is it? Is it kind of a combination of all of that? Talk to me a little bit about that.

Kailey Killoran: 10:21

I think so. I mean, I would love to say that it's just that I have have been a badass throughout my career, but I think that that maybe we'll just say that.

Alex Turkovic: 10:28

We'll just say that.

Kailey Killoran: 10:30

I think there's probably two things that I would call out. So one I have been really lucky to work with amazing leaders, who I think, have given me exposure to Different elements of the business that I was a part of and that maybe wouldn't always be typical for the role that I was in, and so I've definitely benefited from amazing leaders who've spent a lot of time with me and and Given incredible mentorship to me and given me exposure to some of those opportunities.

Kailey Killoran: 10:59

But I do think the other pieces that you know, coming back to what I was saying before, around kind of growth plans within customer success, I think for so long people have anchored to this sort of linear growth plan of you know to use a CSM example, your CSM, your senior CSM Then you start managing teams and then you continue to grow from there and that certainly is an available growth path and I think probably aligns with sort of the path that I have ended up taking myself. But it's not the only path and it it requires you to have a specific interest in leadership and what, what is involved in leadership.

Alex Turkovic: 11:35

And for me, I think the things that.

Kailey Killoran: 11:37

I have always Gravitated towards and wanted are, won the ability to Help and coach people and make that connection with folks on on the team. And then I think the strategic part of my role is is the part that has always excited me the most, and so trying to unpack some of these larger Problems and understand, you know, what the root causes are and build a strategy around that, that's something I've always been passionate about, for sure, but it is. You do have to have a passion for some of those things, I think, to be to be successful in leadership.

Alex Turkovic: 12:13

Absolutely. I mean, there's so many examples, especially in sales, I will say where and, and a phenomenal seller is promoted into a leadership position, only to become a phenomenally horrible leader. You know, because those skill sets don't really it's not a one-to-one thing. As a leader, you have to. In fact, it's kind of interesting because as a, as a leader, you have a lot of the same Traits, or should have a lot of the same traits, that we have kind of intrinsically in CS as well. It's about understanding those sides and being able to work with people and and and Coaching and enablement and all that kind of stuff. We don't. We're almost, like you know, leaders and managers to our customers sometimes.

Kailey Killoran: 13:01

Yeah, I think it's. It's important to call out, as you said, I think the the story you kind of outlined is a story that I think a lot of people have experienced in some way in their career. You know, working with a manager who maybe wasn't right for the role. I think a big way to avoid that is to make sure that it is clear to people that that isn't, that isn't the only role to grow Into and it's not the only option to continue to develop. And if you, it's okay to say I don't want to be a people manager or that's not the that's not the area that I want to lean into in my career.

Alex Turkovic: 13:34

Mm-hmm, I think so too, I there. There is a particular instance. I won't name names, but I once worked with a leader. He was a, he was a manager in engineering and he was doing well and you know, everybody respected and loved him. He was a great leader, but he just decided that it wasn't, for he wanted to go code. He just wanted to go code, yeah, and so he became an individual contributor by choice and I and at the time that wasn't, you know, it was an early learning experience for me, because it wasn't like. You know is the natural progression as you get into leadership and use, you raise in the ranks and all that kind of stuff. But it's okay not to do that too.

Kailey Killoran: 14:17

Yeah, for sure. You just have to make sure that that pop is is clear for people.

Alex Turkovic: 14:21

I think yeah, yeah, I think so too. Okay, enough of that. It was good stuff, but we are here to talk about digital customer success, and one of the things that I ask all of my guests is basically their elevator pitch of digital CS, because it's different with everyone I talked to, because of Different backgrounds and scenarios and things like that. So I would love from you your 32nd elevator pitch of having to describe DigitalCS to somebody who doesn't know what it is.

Kailey Killoran: 14:52

Yeah, it was interesting when I was preparing for this.

Kailey Killoran: 14:54

I actually went back to so when we created our DigitalCS program or department and I'm sure we'll talk about how that's evolved over time.

Kailey Killoran: 15:04

But one of the things that we did was we wanted to create a mission statement to communicate to folks within the organization to talk about why are we doing this and what is Digital Customer Success and what are we hoping to accomplish. So what we communicated to the company at the time is that we were really launching a DigitalCS program to help accelerate adoption for our customers through an automated engagement experience which would enable our CSMs to provide proactive and strategic consultation. That certainly evolved since we originally launched the program, but the two things that I would definitely call out that are important within that are that one, it is a strategy that affects and services all of our customers. We really wanted to make clear that this is not one small segment of customers that will benefit from this type of support. We also wanted to call out that there's very much an external focus, of course, with how we're supporting customers, but also an internal focus when we think about how we can scale the experience for our CSMs or folks on the CS team.

Alex Turkovic: 16:10

So important. It's funny. I mean, a running topic on the podcast has been this notion of DigitalCS moving beyond being a segment and moving beyond just being customer facing and really helping the internal folks to be more effective. It's a really healthy place that we are. I love that. I think it's cool that you're going into designing the digital program with those goals specifically in mind, because I think so many. I mean, even since I started building a digital program, the entire talk track around it has completely shifted to this place that we're at today.

Kailey Killoran: 17:01

So, yeah, no one is saying Tech Touch nearly as much in the industry as they were before, but I think you and I have talked about this before.

Kailey Killoran: 17:10

but it was fortunate to be at the Gainsight Pulse Conference earlier this year and, of course, there was so much discussion around DigitalCS and CS at scale, and a lot of that discussion to your point centered around this idea that digital is a strategy, it's not a segment.

Kailey Killoran: 17:28

And it was a good learning for me because when I initially heard people talking about that at Pulse, my thought was, yeah, of course, like that's how we've always positioned it internally, it's a strategy that is going to benefit all of our customer base and a lot of our internal stakeholders as well. But then the learning really came to me when I sort of understood how some other teams were really perceiving what we were doing with DigitalCS. Despite thinking that we had gone out and explained to the company that this is a strategy that benefits all of our customers, I think there was still a lot of just older thinking about. People still have the perception that it was just about this small digital segment of customers, and so, even having thought that that was sort of the language that we were using, it really made me realize and made us rethink how we sort of wanted to rebrand ourselves internally to make clear that that was for sure the initiative we were working towards.

Alex Turkovic: 18:25

Right, it's not, you're not just. I think the assumption is, hey, you're just sending emails to this subset of customers.

Alex Turkovic: 18:34

Yeah, for sure, and I think you bring up a really amazing point, which is to say that there isn't.

Alex Turkovic: 18:44

It's not enough to build a strategy and vet it with the executive team and then go and build it in whatever CSP or whatever tool you have. There's the internal socialization of this. Is what we're doing, these are our intentions and all that kind of stuff, because one of the sticking points that I've run into in the past is hey look, you've got a marketing team that's doing stuff, you've got a support team that's doing stuff, you've got a product team that's doing stuff. There's surveys going out, there's emails. They all look a little different. And so I guess this kind of segues into the next question, which is I feel like we get a little bit of a bird's eye view in talking to you as to getting a digital motion up and running which is unique and thank you for your vulnerability there but how are you at Lupio kind of looking at organizing around digital CS? How are you not just communicating that out but also coordinating with the other functions around you?

Kailey Killoran: 19:56

Yeah. So I think there's probably two areas of that that I would call out. So one I think everyone has a different experience of this. Depending when you decide to launch a digital or scaled CS program, I think if you're really lucky, you find the sweet spot that is kind of not too late and not too early. I do think it's very easy to launch too early and not have built the appropriate amount of trust with your customers in order to be able to engage with them in that way. But it's also, I think, it's hard to change old habits and so if you have CSMs that are working very closely with customers, it can be hard to manage that change within an organization.

Kailey Killoran: 20:40

But the reason I mentioned that is because I think we were really fortunate at Lupio that when we decided to formally launch this program, we had already built out so many specific functions within our customer experience department and, you know, built out the experience that our customers were having.

Kailey Killoran: 20:59

So it's very different launching a digital program when you already have a strong customer education team and great education resources for customers, when you already have a really robust support center and support team and support resources, and so then you really are, I think the challenge that we have sort of been working towards is okay, how do we then replicate the strategic advice that CSMs are providing today through digital or scaled resources? So that's kind of the initial problem that we have been looking to solve in creating sort of version one of our digital customer success journey. I think that's very different. If we were doing it a lot earlier, we'd be thinking about, okay, well, how do we just get these baseline resources set up so that we can get customers, you know, not coming to CSMs with support questions or not working directly with CSMs for training or that kind of thing. So that probably gives some context as to the world in which we were launching this digital program.

Alex Turkovic: 22:03

Yeah.

Kailey Killoran: 22:04

And the second piece, which I think you touched on and there's so much to dig into here but really comes down to trying to drive as much clarity around roles and responsibilities as possible, and I think there's probably some areas where we did that really well and then probably some areas where we definitely have learnings in terms of who owns what and how do we make sure that it's clear. I think the biggest areas that we really leaned into at the beginning were, you know, thinking about from an operations perspective and the systems that we're going to support our digital CS programs. You know, to what extent do we want CS owning the strategy and execution? To what extent does revenue operations own the strategy and execution?

Kailey Killoran: 22:50

And I think that the difficult thing in here is that there's always going to be some areas that overlap. There's never going to be a totally clear cut. You just do this and you just do this and that will be good to go. So we define those roles and responsibilities right at the beginning, but we've also been open to learning about what's been going really well. And then you know areas that we maybe had some opportunity to change, I think the relationship with operations, marketing, education and how we've thought differently about bringing that into our CS. At scale structure, those are probably the biggest three that I would call out as sort of areas of potential confusion to get ahead of. So a big part of what we've tried to do from the beginning is at least attempt to define those roles and responsibilities and then, of course, be open to changing them along the way.

Alex Turkovic: 23:45

It gets more complex too when you start talking about, you know, cohorts of customer by status, like, are you going to do the same thing with your at-risk customers that you are with your you know everything's hunky-dory customers? Absolutely not. And so who owns that bit? And like, where does that? It starts to branch really quickly and get complex really quickly. So I appreciate the challenge for sure.

Kailey Killoran: 24:13

Yeah, yeah, we've definitely had some learnings along the way, and I'd like to think we're doing it better now than we were six months ago, and I'm sure six months from now we'll also have some learnings to share then.

Alex Turkovic: 24:25

That's really hard, though, because, you know, six months in most of our lives professionally is ages right. Everybody's moving fast, everybody's doing a ton of stuff. It can be really hard to lose sight of the improvements that you've made over time, and I think a big part of implementing a strategy like that is like celebrating your wins. It's like, hey look, this is where we were two quarters ago, this is where we are today. We're not where we want to be, but we're a heck of a lot better than we were before.

Kailey Killoran: 24:59

Yeah, I think that's super important to call out and actually so, when we launched our digital CS program, I think one of the key things for myself and for other leaders was we brought someone in to really own that program, because we sort of had this large goal of, yeah, we're going to launch a digital customer success program, but if someone's not working on that all the time and doesn't have it as their main priority, it's just too overwhelming.

Kailey Killoran: 25:26

So we hired someone on our team, jace, who leads our digital CS efforts, and she has been amazing in terms of taking ownership of that. But that's what you highlighted is something that she and I have talked about a lot, which is I know we have this grand vision of where we're going to get to, but it's really important to pause and think. You know, this one communication that we're sending out now that doesn't seem like it's that hard, but you know, took six months to set up. You really have to stop and celebrate those wins because, to your point, we're probably never going to get to the final version of the grand vision. Once we do, we'll just create another vision from there. So if you don't stop and celebrate those wins along the way, it can feel really overwhelming.

Alex Turkovic: 26:09

Totally, absolutely, absolutely. You touched a little bit earlier on tooling and there's a pretty large camp that would basically say, yeah, tooling doesn't matter, you use what you have, etc. Etc. Some people with really strong opinions on that. I like to nerd out on tools, so we're going to nerd out on tools a little bit. What does your tech stack look like, what are you working with and how do you see that evolving?

Kailey Killoran: 26:35

Yeah, so I would say that the three main tools that we're using today are Gainsight as our customer success platform, and then we use Pendo for in-app guidance and we use Skill Jar for our customer education program. I think what I see evolving over time is that our tech stack will evolve to become more holistic, and I don't mean that to say that we will consolidate tools under one platform or that we need to be using one group of tools.

Kailey Killoran: 27:08

What I do mean is that we need those tools to talk to each other in the right way and we need the same data and reliable data to be accessible in each of those areas. So how do we make sure that we're leveraging the goldmine of information that we have in our customer engagement with our learning station courses? How do we use that to inform the experience that they are getting through our digital programs that are generally set up in Gainsight? So I think the biggest shift or evolution that we'll see is making sure that those integrations are either very robust and then, of course, I know there is a lot of consolidation of shuels happening within the market as well, but I don't think that's necessarily the approach that we need to take. But we do need to make sure that the data is the same and reliable across all of those systems.

Alex Turkovic: 28:00

Yeah, my experience, and I would imagine yours, is similar in I'll call it plunking a digital motion or digital CS program on top of an existing business that's had years of legacy data and all that kind of stuff. Is that really? The data requirements for a healthy digital program are, in some cases, vastly different from the data requirements of your traditional kind of CS and sales relationship, like there are things that we need to run digital programs that may or may not be captured in Salesforce or may not, may or may not be there or are different in different systems, just because people haven't needed that data to be the same across systems, and so I think you know. What that brings to mind to me is that anyone who is implementing a digital program, especially into an existing business, you're going to have to get in the weeds on data.

Alex Turkovic: 29:07

I mean that's just the way it is and I'm curious what your experience there has been. And also, on a related note, like, what other barriers have you encountered or are you still encountering that you're actively kind of solving for?

Kailey Killoran: 29:20

I mean, if you know anyone who has gotten the data piece perfect, I would love to chat with them. So we've definitely encountered some, I think, a couple of the things that I would highlight. So one it can be really overwhelming to dive into this because there is so much data that you can pull in and I don't think anyone wants to make the decision off the back that we want to close the door on access to some of that data. But you do really need to work through when do we want to prioritize? Because it's going to require so many internal resources to make sure you have access to the data. You need even just one small piece.

Kailey Killoran: 29:58

So saying we just want to bring in everything and then see what we can do with it is not, it's not a helpful strategy. So that's one piece, I think, is just working through the kind of prioritization. And so for us, you know is it, do we need additional product data? Is the data from our education team or learning stations? Is that where we want to prioritize? So really working through that is important. And then I think this comes back actually a lot to what we were talking about at the beginning in terms of surface processing, the importance of digital CS initiatives across the organization because we rely so much on other teams to ensure that we have the right access to data. It's not something that we can do on our own, and so it's not just communicating the need, it's communicating the impact of the program and making sure that other folks from engineering or operations are all thought into that so that you have the support you need to actually get that access.

Alex Turkovic: 30:58

And it would like all. Well, this gets into, kind of, my next question, which is really around the PR element of it, which we talked about and and you know it's kind of touched on but like the importance of communicating cross functionally what you're doing, what impact is having, and those kinds of things, because you know awareness is key. I mean, I'm thinking about, you know, scenarios that have happened to me in the past where you know product comes and says, hey look, this is ready to go, ready to sell, and there's been no communication. There's like there are no sales materials, there's no skews in the system, like it's like, okay, you built this thing, you know now what. But but it's kind of like you know, integrating yourself into all these different kind of go to market processes and then beyond, like the support processes and whatnot as a digital programs, is super important. So how have you tackled that PR? How have you integrated with the other leaders and peers and folks from around the company, especially maybe the C-suite as well?

Kailey Killoran: 32:13

Yeah, I think so One at a company level. We've been really lucky that I think organizationally the importance of customer success has always been really well understood. I think we've been you know we've never found ourselves in the position where we're having to justify investments in CS or remind people of what the importance of CS is. So that's a great place to be starting from.

Alex Turkovic: 32:40

I think the other.

Kailey Killoran: 32:42

The other piece at an organizational level is that we have, I think, done a good job of communicating the importance of these initiatives even up to our largest enterprise customers. So I think when people can see a clear line between the programs you're running and your ICP or your target market, that really helps to drive home that this isn't just for one segment of customers that maybe I don't really need to worry about. If I go one level down, though, I think so. Just recently, when we've been rolling out some of the first iterations of these programs, one thing that we did was work really closely with the sales leaders and also be really available for training and communications to sales folks who are on the ground selling our products to customers who are going to eventually be having this digital experience. I think it's really important for them to hear the excitement and the confidence from myself, from the manager I mentioned earlier, that they're going to ask questions about are we concerned about this? How are we going to make sure that X doesn't happen To hear us respond directly to those questions, not just with an okay answer, but with excitement and confidence and excitement to learn. I think it's been really important Then also hearing that from their sales leaders and ensuring that they have the same confidence that we have and we can speak clearly to how we're going to measure progress along the way makes a big difference. Then I think the final piece of that is a willingness to engage with customers and just the knowledge that we're not going to get it right all at once.

Kailey Killoran: 34:31

I think the biggest question that's come up from our sales team and then, of course, even from a lot of the CSNs on the team as well, is we're moving customers over to this digital experience. What is going to happen if customers don't like that, if they push back and say I don't want to engage in this way or this doesn't work for me? Are we just going to shut the door and saying no one can speak with them? That's certainly not the approach that we want to take. But I think we're really clear that, first of all, engaging in a digital program doesn't mean you never talk to anyone from our CS team again that's not the intention of the program by any means but also that myself and other leaders are really willing to engage directly in those conversations and be clear with customers about why we're doing what we're doing and our confidence that it will serve their needs, but also be really open to hearing how are you working with your CSM today and what areas of concern do you have that you won't have access to in this new way of working with our team?

Kailey Killoran: 35:31

I think there's probably some things that we will hear in those conversations where we say, okay, I'm confident that we'll be able to deliver that through these programs. Here's how let's try it, see how it works and share feedback along the way. But there's also probably some things that we will hear and say, yeah, I understand that concern and maybe we haven't spent enough time building that out in the program and that is an area where we wanted to vote. More resources, I think, just an openness to feedback, a willingness to directly engage. So if we're asking CSMs to have these types of conversations or navigate some of this pushback, that I'm very willing to hear that feedback as well, and that we don't just want to hear it when it comes up as an issue. We want to be proactive about garnering that feedback from our customers.

Alex Turkovic: 36:22

We're all very bought into the talk track of digital is not a segment and it's a strategy Great but it's a big one here when it comes to sales and sales confidence in the post-sale.

Alex Turkovic: 36:43

I think what you touched on there is really critical, because how many times have we experienced a post-sale experience where, for a smaller segment customer, they get onboarded and then, unless they're talking to support, it's like a ghost town.

Alex Turkovic: 37:05

It's like there's no support whatsoever. If I'm a seller and I know that there's this digital program in place that does engagements whether it be email or in-app or SMS or whatever it is and that there is a team behind it that a customer can actually engage with if need be, that to me gives me much more confidence and is also an additional talking track and a value point that you can really drive home with a new account or get feedback from as part of a renewal. That is so cool. I think very often overlooked because we just implement this stuff and we try to help the customer and things like that. But then you got to also make sure you're engaging with the seller and socializing these things with the seller and making sure that they know that, hey, we're building this ecosystem. That's something you can talk about on every phone call.

Kailey Killoran: 38:04

Yeah, For sure.

Kailey Killoran: 38:05

I think what's helped to drive that home for us to some degree is one leading on previous data in terms of how our customers are engaging with us and making sure that the sales team has a good understanding of that.

Kailey Killoran: 38:19

This program is designed to help our team scale, but it's also based on what we've observed about how often our customers want to be speaking to our team or how often they just want to self-serve with some of these resources. But I think you touched on renewals, and building out what that digital renewals process looks like has been a big part of our first iteration, and one thing we were really clear about throughout the entire building process was at no point do we want to make it impossible or even really hard for customers to connect with us. We may be automating a lot of this communication and, sure, if the ideal version may look very low-touch, but at every single point you have the ability to say I want to connect with someone from the team, I have questions, I have concerns, and I'm sure that will evolve and look different over time, but we don't ever want to remove that. We always want there to be an option to say our team is here and here's how you can connect with them.

Alex Turkovic: 39:19

Yeah, I've even had the thought of branding the link to book a call A less annoying version of Clippy, maybe. But you put a brand around the fact that, hey look, you can connect with somebody in our pool team, or whatever it is, at any time, and it's not just a link or a button and an email. It's like there's maybe some brand to it. I don't know, could be an interesting thing, but that's just me thinking off the top of the dome.

Kailey Killoran: 39:49

I think we've also found the there is a certain amount of consistency you can provide to customers in working with a digital team that you're just never able to guarantee in working with one CSM. Csms grow in their careers, they grow into new roles, they grow into other companies, and so there is an element of consistency in saying this is how you will work with us and how you will work with our team moving forward. That, I think, has actually been a positive element for us to highlight in customers who are making that change as well.

Alex Turkovic: 40:23

Yeah, absolutely. There is a lot of talk in the CS community in the community about how to do handoffs and how to handoff not just between sales and post sales, but then, to your point, csms inevitably shift around and you have to reassign accounts and it's a big pain in the butt for the customer and for the leadership and for the CSMs involved. I love what you said about removing maybe a barrier or removing a layer of complexity to that handover, where there's always this sense of hey, we got you, whether it be with a person or whether it be with a link to a person.

Kailey Killoran: 41:09

For sure. I think everyone's had the customer experience somewhere. I'm thinking of some B2C products where, no matter what goes wrong, it's impossible to get a hold of someone, and that's very much not what we want to be providing to customers. We want to have a very open door so the customers can engage with us at any point in the journey.

Alex Turkovic: 41:31

Yeah, absolutely. That is easier said than done.

Kailey Killoran: 41:37

For sure. Yeah, sounds great in theory, definitely harder to execute on in reality. Yeah.

Alex Turkovic: 41:42

Absolutely Well. Look as we round out our convocations. Your time is crazy valuable and it is also Friday. I don't want to stand between you and your weekend. I'd love to understand a little bit more about what's in your content diet, what are you digesting? What are you paying attention to out there Podcasts, books, newsletters, whatever it be.

Kailey Killoran: 42:04

Yeah, I always struggle with this question. From a professional standpoint, I will make an admission, which is that I am a huge reader. I don't love business books and I don't love a lot of content that's created around that. I actually find that the best way for me to consume new information about what is going on in the industry is connecting directly with folks. I know that that's probably easier said than done, but I think in CS it's actually a lot easier than it sounds. I will always sing the praises of the CS community. It is so easy to connect with folks and I think we've seen that as we've built out our digital programs. Everyone is really excited to learn and discuss with each other what's going well and what's not. I think the engagements that I find most helpful are often those networking or webinar events that bring people together and then continue a conversation from there. I will admit, from a content perspective, there's not a ton of CS content on a regular basis that I'm consuming in that way.

Alex Turkovic: 43:17

But from a networking perspective.

Kailey Killoran: 43:19

I find that helps to surface a lot of those newer ideas and trends.

Alex Turkovic: 43:24

It's so huge. I have a growing number of people that we've interviewed have mentioned LinkedIn as a big resource, because that's your place to connect with people and things like that. There's other communities as well. There's actually a brand new Slack community. I don't know if you're in it, but it's called DCS Connect, which is all about digital CS in its infancy, but if you're not in it, I'll send you the link.

Kailey Killoran: 43:56

I have a lot of conversations with folks who are looking to transition into CS. The three resources I always recommend are to your point. There's a couple of Slack communities. I find a lot of the resources the Gain site or Catalyst or others provide. There's a wealth of information out there that is easily accessible and not gated in any way. Then I will always also recommend the Success Hacker of certifications, but those first two. You don't necessarily need to be looking at that information every day, but if you have a question about how should I go about setting up this program Often you will find that a lot of folks have had that question before. There's a lot of resources to look back on and help get folks set up in that way.

Alex Turkovic: 44:43

They really are. And to your earlier point, the CS community has no shortage of people that are willing to hop on the phone, really no matter what level. People are very generous with their time in CS, which is so cool. And yeah, it's cool.

Kailey Killoran: 45:04

It's a thing that's very consistent over time as well. I think about the time at which I transitioned into customer success, and I think that's as true, if not more true, now than it was a few years ago. I think the worry you always have as a community grows is that it is harder to connect and people are maybe less likely to make a connection like that, but that's still very much not the case.

Alex Turkovic: 45:28

Yeah, I totally agree, absolutely. Speaking of the community, is there anyone you want to give some kudos or shout out to that's doing cool stuff, or somebody that's helped you out as you're getting into this world of digital and really building out that program?

Kailey Killoran: 45:45

Yeah, for sure. Speaking of leveraging LinkedIn, I really should reach out to this person because I don't think that they know how big an impact they've had on our CS at scale efforts. But one of the discussions that I enjoyed the most when I was at Pulse was by Deepina Kapila I believe is how you pronounce her name from Miro and she gave a great discussion on product versus sales, like growth, and thinking about CS at scale within that, and similar to the light bulb moment I mentioned earlier that was a huge light bulb moment for me in thinking about how we leverage our existing teams within one department of CS at scale to create a holistic customer journey.

Kailey Killoran: 46:29

I think prior to that and probably you and I chatted about this before I've had that light bulb moment as well, but I really was struggling with this piece of how do we put these great things we're doing together with customer education and now we're building out this digital customer journey. What is really the ideal structure to support that? And listening to her chat at Pulse really set off a lot of ideas and has created a lot of very positive change for us actually over the last couple of months. So, on the topic of how small and tight the community is, I really should let her know how much she's influenced our work structure.

Alex Turkovic: 47:09

Well, on that, shout out to Dee, she and I well, we're both in Austin and I used to work with her significant other and so we kind of knew each other through that. So it's a very small community, but I totally agree, and we'll put a link to her session at Pulse in the show notes.

Kailey Killoran: 47:28

So you guys can check it out too. I should have assumed you were already connected. Everyone in the community comes full circle at some point. It's funny.

Alex Turkovic: 47:37

It's funny. Yeah, she and I actually talked about I think she'll be on the podcast at some point soon too. So come on, dee, let's go. Lastly, you know, where can people find you and engage with you? I mean LinkedIn, obviously. But you know, are there other things you want to point towards?

Kailey Killoran: 47:56

I think LinkedIn is probably it. Honestly, I yeah, I'll typically share semi-semi regularly there and I'm always happy to connect. Like I said, it's been really rewarding for me to you know I see how much some of these messages have resonated with folks and also to have the ability to kind of directly mentor and coach folks who have connected with on LinkedIn. So I'm always happy to, always happy to connect there and have been really grateful for the opportunity to provide some of the mentorship back that I've been lucky to receive early in my career.

Alex Turkovic: 48:31

It's awesome. Yeah Well, I've super appreciated your time. Thank you for joining me. It's always great chatting with you and you know first Canadian on the podcast, yay.

Kailey Killoran: 48:44

I will be able to add to my LinkedIn profile.

Alex Turkovic: 48:46

Sounds great, but thank you so much for having me.

Kailey Killoran: 48:50

I've been so looking forward to doing this and I've loved all the conversations that you've shared so far and I think I've said this to you before, but it's with all the discussion around digital CS. I can't believe someone wasn't doing this already. So, yeah, kudos to you for getting things started and centralizing an important discussion that I know is on a lot of people's minds.

Alex Turkovic: 49:10

Just riding away, man Just riding away. It's all good. Yeah, thank you for your time.

Kailey Killoran: 49:16

Thank you.

Alex Turkovic: 49:17

Thank you for joining me for this episode of the Digital Customer Success Podcast. If you like what we're doing, consider leaving us a review on your podcast platform of choice. It really helps us to grow and to provide value to a broader audience. You can view the Digital Customer Success Definition word map and get more details about the show at digitalcustomersuccesscom. My name is Alex Turkovich. Thanks again for joining and we'll see you next time.