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Episode #133 Defining the CS Playbook Philosophy to Balance – Guidance and Governance ft. Caitlin Wood (ZeroFox)

#updateai #customersuccess #saas #business

Caitlin Wood, Chief Customer Officer at ZeroFox, joins hosts ⁠⁠Kristi Faltorusso⁠⁠, ⁠⁠Jon Johnson⁠⁠, and ⁠⁠Josh Schachter⁠⁠. They discuss the intricacies of customer success in the cybersecurity industry, along with her unique insights into the challenges and triumphs of leading a customer success organization—especially in the realm of cybersecurity, where the ROI often means that nothing happens.

Tune in as Caitlin uncovers how she approaches customer experience, the evolution of customer engagement models, and the balance between AI integration and the indispensable human element in achieving customer success.

Timestamps
0:00 – Preview, BS & Intros
4:08 – Learn about ZeroFOX
5:10 – Challenges in Proving ROI in Cybersecurity
7:45 – Customer Engagement and Service Model
10:57 – Lead Pass Process and CSQLs
15:10 – Complexity and Simplicity in Incentives
18:10 – Efforts to Mature Models and Remove Friction
22:35 – Adaptation of Playbooks
25:51 – Attitude, Aptitude, and Experience in Hiring
30:56 – Integrating AI for Internal Teams & Tasks

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👉 Follow the podcast
Youtube: https://youtu.be/JprAz-o-dWk⁠
Apple Podcast: ⁠https://apple.co/3dfWXmD
Spotify: ⁠https://spoti.fi/3KD3Ehl⁠


👉 Connect with the guest
Caitlin Wood : https://www.linkedin.com/in/caitlinewood/

👉 Connect with hosts
Jon Johnson: https://www.linkedin.com/in/jonwilliamjohnson/
Kristi Faltorusso: https://www.linkedin.com/in/kristiserrano/
Josh Schachter: https://www.linkedin.com/in/jschachter/

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Unchurned is presented by UpdateAI

About UpdateAI
At UpdateAI our mission is to empower CS teams to build great customer relationships. We work with early & growth-stage B2B SaaS companies to help them scale CS outcomes. Everything we do is devoted to removing the overwhelm of back-to-back customer meetings so that CSMs can focus on the bigger picture: building relationships.

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Jon Johnson:
Welcome to Unchurned podcast of CS professionals talking about CS professionals. I am one of your hosts, John Johnson. We also have Christie Falteruzzo on with us. And in the background, Josh Schachter quietly wishing that his microphone worked. Christie, how’s your week been?

Kristi Faltorusso:
My week has been great. It’s Monday. So, you know, all seven hours of my week so far have been fantastic.

Jon Johnson:
Absolutely. Well, we, I’m pretty excited about today. We have a really great guest. I would like to introduce Caitlin Wood, to the group. She is the current key chief customer officer at Xerofox. Caitlin, how are you doing today?

Caitlin Wood:
I’m great. I’m so happy to be here. Thank you guys so much for having me.

Jon Johnson:
I love it. Well, my favorite part about this podcast is that from the point that we started recording, everybody thinks we’re super professional. But, like, the ten minutes before we hit recording was absolute chaos. So thank you

Kristi Faltorusso:
for your help. That we’re very professional? Like, do we know, like, we have nobody. Okay. I didn’t think so. Not a single person. The seven people that are listening, I am pretty confident that they didn’t think that we were, but I wanted to just confirm with you. You. Thank you for that.

Kristi Faltorusso:
Yeah.

Caitlin Wood:
Nobody takes longer to set up a recording or work on it than technology executives in a room and

Kristi Faltorusso:
see how long it takes them

Caitlin Wood:
to start a zone.

Jon Johnson:
Yeah. Right? I mean, I don’t

Kristi Faltorusso:
know about you guys, but the biggest miss for me in this fully remote first work world is not having IT at my disposal. Right? Something doesn’t work, I can’t call for help and, like, scoot my chair back and get out of the way. Now it’s like I have to go and fix things, and I’m very not equipped to do that. Well

Caitlin Wood:
either makes you feel powerful or powerless. Right? Yeah. Yeah.

Kristi Faltorusso:
I’m powerless at all all the time. I’m very sad and stressed.

Jon Johnson:
I actually planned ahead. About twenty years ago, I had a son.

Kristi Faltorusso:
Yeah.

Josh Schachter:
And he is my my tech

Jon Johnson:
support at this point. And it it has taken

Kristi Faltorusso:
so way ahead of things.

Jon Johnson:
It’s taken a lot of therapy to be proud of the fact that I have a, like, a son who’s in college, and not feel like a grandpa.

Josh Schachter:
So but that’s not what we’re here to talk about. Josh

Kristi Faltorusso:
I mean, it could be.

Jon Johnson:
It could be. Josh puts you in this great document, from our call. I’m not gonna read it.

Josh Schachter:
I’m just gonna cut it down. I would prefer to talk about the therapy, your therapy sessions then so we can shift over if you’d like to make an audible. Yeah.

Kristi Faltorusso:
I mean, it’s it’s usually one and the same.

Josh Schachter:
Yeah. Yeah. I mean, look. We all know that customer

Jon Johnson:
success is therapy. Right?

Kristi Faltorusso:
No. We need therapy. I don’t know that we are therapy.

Jon Johnson:
I didn’t say it was good.

Kristi Faltorusso:
Okay. Okay. Just checking. Alright. Okay.

Jon Johnson:
Well, Caitlin, I would love

Josh Schachter:
number normally, what we do

Jon Johnson:
in these things is is kind of we talk through organization, how you kind of think about customer success.

Josh Schachter:
Give us, like, a quick little, like, elevator pitch, and then

Jon Johnson:
I wanna know how much you’ve spent on therapy.

Caitlin Wood:
Yeah. Sure. Okay. So how do I think about customer success is the question Mhmm. In general? Alright. I think everyone probably gives pretty much the same or similar vein of answer to this, but I think about customer success as customer experience plus customer outcomes. And as customer success professionals and our teams are here, just make sure our customers are able to maximize value and realize continuous value from our solutions.

Jon Johnson:
Got it. And since you’re sitting up at the top, chief customer officer, what does your influence look like for the rest of your org? I’m talking all the way down. Is it director, manager, IC? Kind of walk me through, like, the architecture of your reporting structure.

Caitlin Wood:
Sure. So I’ve got five departments that roll up under my organization. And that’s you think about it from the beginning of the customer journey. That’s starts with our onboarding education. So onboarding and customer training, your traditional CSM and technical account managers, customer support, success operations, which we would get nothing done without success operations. They’re Operations. All the glue. And then I also have our 20 fourseven managed security services.

Caitlin Wood:
So ZeroFOX is a cybersecurity SaaS platform. We sell also managed security services

Kristi Faltorusso:
Got it. Part of

Caitlin Wood:
our platform is. So all of

Kristi Faltorusso:
our 20% in function is

Caitlin Wood:
you as well.

Jon Johnson:
Got it.

Kristi Faltorusso:
That’s Caitlin, can I can I ask a quick question here? Because I’m always fascinated by the security space because you’re selling insurance. Right? Yeah. So it it like, proving an ROI is so tough in this space because your ROI is nothing happened.

Caitlin Wood:
Right.

Kristi Faltorusso:
So

Jon Johnson:
Nothing hap that man, that’s brilliant.

Kristi Faltorusso:
Right? Yeah. Yeah. Like, hey, customer, did anything happen this month? Nope. We did it again.

Jon Johnson:
Give us more money.

Kristi Faltorusso:
Hey. Value. So Well help me understand how you work with customers to articulate the value there.

Caitlin Wood:
Sure. I mean, so we’re a really unique place within the cybersecurity industry. So what we do is we provide intelligent solutions around discovering and protecting digital footprints for enterprise customers. So what that really means is we are providing customers with intelligence about emerging threats. We’re helping them to map their public tech service. We’re protecting all of their digital assets. And then we’re also helping them to disrupt attacker infrastructure or exposures that might be out there. So what’s unique about this is because we’re operating outside of the traditional cybersecurity perimeter, things actually do happen, and we can help them take action against those things.

Caitlin Wood:
So a phishing website gets spun up. We can actually help have that removed. We can work with customers to remove things like impersonations of their executives across social media. So those types of things are really helpful improving ROI, but not all customers have those things happening all the time. But when they do, they need something they they need a platform to deal with it. And so you’re right. There is a balance there, of the insurance aspect of it versus the we’re taking down tens of thousands of things for some customers in a year.

Kristi Faltorusso:
Okay, Lynn. In the services that you offer, do you guys have, like, internal teams of, like, hackers who are trying to penetrate these organizations to find and discover some of the the gaps that might exist or the situations that might cause issue?

Caitlin Wood:
Yeah. So this is it’s all publicly available data, which is, I think, the the tough part to wrap your brain around because there’s just so much out there that no one team can do this all manually. And so what we’re effectively doing is we are ingesting a whole bunch of sources from the surface web, from the deep and dark web, and, analyzing that information to identify potential threats to our customers. And so that is, like, that’s what the ZeroFOX platform does. And then we have teams as part of our managed service that are reviewing all that content and telling our customers what they actually need to know, what they need to prioritize, and then helping them deal with it.

Kristi Faltorusso:
Where does the CSM and the managed services team start and stop?

Caitlin Wood:
Yeah. So this has been a part of our evolution. Right? We actually spent the last year totally transforming our customer engagement model, and this was at the crux of that conversation. So as we built and scaled and grew, we were growing a an account management function within sales, and then we also so you guys, I talk with my hands a lot, so you’re you’re seeing a lot of

Kristi Faltorusso:
I’m Italian from New York. This is the only language I know.

Caitlin Wood:
Yeah. This is how I this is how I explain. So, as we grew, we grew up in a a an account management function that’s in sales that was responsible for our renewals, our account growth. And then we also grew up as managed services function or a traditional support function and specialized teams that helped in the more technical aspects to help supplement our account managers. So think of, like, a technical account management service. Right? What we found was a gap in the middle. So you have a 20 fourseven managed service that is by nature reactive because they are, they are reacting to the data that our platform collects and alerts on for our customers. And then you have account managers that are they’re doing business reviews, they’re focused on, ensuring our customers are successful, but they’re not platform experts, right? They’re they’re a little bit of a hybrid.

Caitlin Wood:
And so our journey over the past year has been to create a new customer success function from zero to one that takes that that middle piece that our customers are really that’s what they’re asking for. That’s what they really are seeing value out of, and almost scales the technical account management model out, totally redoes the swim lanes between what success and sales are responsible for and helps us drive more value for our customers that way.

Kristi Faltorusso:
Caitlin, have you guys designed, like, a pod structure? So is it that you’ve got, like, the same account manager and CSM and services team members together for book of business? Is it how how tell me how is it aligned? Like, how

Jon Johnson:
do you

Kristi Faltorusso:
have these teams okay. So how are they working together?

Caitlin Wood:
It’s not a pod structure. It is based on we as a part of this, we had to redo our customer segmentation as well. Right? So as you can imagine, we’re trying to

Kristi Faltorusso:
align our yay. It’s everyone’s favorite that way. All of the things.

Caitlin Wood:
All of the things. Yeah. It’s like, I have a great idea. We’re gonna do this one thing, and then it’s hundreds of waterfall changes,

Kristi Faltorusso:
right, that you’re that you’re managing.

Jon Johnson:
It’s like glitter. Like, you just never get rid of the next thing.

Caitlin Wood:
That’s right. That’s a great amount. I love it. So we have a a similar segmentation model pyramid structure that most organizations have. Right? We have more of a scale digital presence. Bottom of the pyramid, top of the pyramid, it’s much more, one to one. And that’s both on the CS side and the sales side. So you’ll have an account manager and a named CSM.

Caitlin Wood:
The account manager will be responsible for account growth,

Kristi Faltorusso:
and the CSM is responsible for adoption and the the data that

Jon Johnson:
Do you do you have a pathway?

Josh Schachter:
I’m just curious about I I don’t know if it’s a CSQL or if

Jon Johnson:
it’s a hand off or kinda what that pipeline looks like. Mhmm. Is that from CSM to AM, or do you have AEs? Do you have GADs? Like, what does that look like?

Caitlin Wood:
Yeah. So we actually launched that this year. That was one of the things I was super excited about, in the second half of this year. As we got, you know we took a phased approach to get into this model. And as we started to align our CSMs with customers this year, we stood up this CSQL lead pass process. And within a quarter, we were able to generate pretty significant opportunities and and contribute to revenue at the end of the year. So that was a huge win.

Jon Johnson:
K. I have a question about that, but I wanna give space for Christie because I did just kinda jump into her three theme. Anything you wanna follow-up on Christie? Because I wanna do No.

Kristi Faltorusso:
Like, I took I took the first couple of questions, John, and now I’m curious to I want you to complete your thoughts. So, like, do

Jon Johnson:
you have the question? Let’s roll with the care.

Kristi Faltorusso:
Let’s go. Let’s go. Let’s go.

Jon Johnson:
How are you thinking about gating those processes? In the past, I’ve seen C SQLs get pretty unwieldy similar to product requests. Right? It’s like, oh, we’ll just put it in the product update, and we’ll let them sort it out. Right? Oftentimes, CSQLs get, you know, handed over. If the CSM is identifying it, is there verification and validation on the other side before it is confirmed as a a CSQL? And then how are those identifying, processes happening?

Caitlin Wood:
Yeah. So first and foremost, something I I tell my team whenever we roll out a change is there’s no chance that we got this a % right the first go around. I think they’re tired of me saying this at this point, but it’s true.

Jon Johnson:
Could you at least once get it right the first time?

Caitlin Wood:
Yeah. The whole the whole time.

Jon Johnson:
Just not

Kristi Faltorusso:
this one. Just not this one.

Caitlin Wood:
So the way I approach these things is, like, start with something simple and then adapt because it’s a lot easier than going in really complex and trying to unwind that. Right? So what we knew worked is we’re having these conversations. We’re identifying opportunities. We ran some campaigns with our CSMs to help them kind of target conversations. The initial feedback that we got was, well, the leads you’re passing aren’t specific enough. There’s not enough detail. We need more information here, and that was from the sales side. From the CS side, it was, I can’t see what’s happening.

Caitlin Wood:
I passed this great lead. What’s going on? This is what I call a seam. So a seam is a gap in between teams. It’s where processes fall apart. It’s where customer friction happens. It’s where internal friction happens. It’s where something is in the middle of not squarely one team or another. And when you experience a seam, you experience friction that could be with your customer.

Caitlin Wood:
It could be internally. And that’s where you typically see, like, finger pointing. Right? A lot of teams will say, like, I don’t understand how they could do this. They completely screwed something up. Right? And instead, it’s, oh, we need to look at this process. Like, this team needs to be enabled with more data. We need to update this workflow. Rarely, the answer to a theme is tell this person to do something better.

Jon Johnson:
Yeah.

Caitlin Wood:
Right?

Jon Johnson:
I love that.

Caitlin Wood:
Yeah. So we are, in the middle of actually updating this process to, for example, remove some character limits in what our CS team can pass over to the account management team as a lead. Put in some some gating on the opportunities so that there is some kind of mutual acceptance when they go and create take this task and create an opportunity, and make it more standardized of how we measure inbound leads. So it’s just the same process that the sales team is used to using, and they’re not having to do something different that lead lends itself to error. So

Jon Johnson:
Love that. Yeah. Did your CSM have

Kristi Faltorusso:
John. No. John.

Josh Schachter:
You gave me

Jon Johnson:
the green light. You said I gave

Kristi Faltorusso:
you the green light for the one question, and now you’re getting greedy. This is why. If you don’t know how to share, I’m not gonna invite you back.

Jon Johnson:
Caitlin, Christy and I love each other.

Kristi Faltorusso:
It’s my turn. It’s my turn.

Caitlin Wood:
I can tell. I can tell.

Kristi Faltorusso:
Caitlin, how are

Jon Johnson:
our Do

Josh Schachter:
you guys need to be

Kristi Faltorusso:
a guest team? Or are you? No. No. Please don’t. No. No. Please. Just stay where you are.

Caitlin Wood:
Yeah. So we’re in do you mean specifically for this process or overall?

Kristi Faltorusso:
Yeah. For for this process specifically. Like, are does the team get paid at all for the qualified leads they’re passing over, customer success specifically?

Caitlin Wood:
After they close. So we’re incentivizing them for leads that actually turn into close success.

Kristi Faltorusso:
Was there any consideration in, like, a partial on it being a qualified lead? Like, so once the sales team qualifies, giving them a a percentage, whatever, would feel healthy, and then saying you get the other on the back end just because it feels like the CS team is doing the work, like, they’re part of the work to bring it to the table. But when they’re handing it over to the sales, they lose control. Right? So is there any cons did you guys have conversations on that?

Josh Schachter:
Caitlin, this is what we call a question that was framed it was framed as a question, but, really, it’s unsolicited advice and a backseat driver. That’s all. I’m interjecting on that, and now I’m getting out of the way.

Kristi Faltorusso:
No. Josh, nobody even invited you back. You’re supposed to be on mute and off camera. You don’t even go here. Caitlin, anyway, tell us about what you’re doing.

Caitlin Wood:
So let’s see. I did think about that. And the way that I chose to approach it is starting simple. So I didn’t want to introduce too many variables the first time we rolled this out. And That’s totally fair. Yeah. So I think it’s something we’ll we’ll evaluate again in the future and as we get good at this and figure out where the break points are and where the behavior needs to change. But at the end of the day, like, I believe compensation plans should drive behavior, and they should be simple to measure and simple to implement.

Caitlin Wood:
And if there’s too many variables, especially the first time you roll something out, it’s gonna drive confusion in the team. So

Jon Johnson:
Not bad.

Kristi Faltorusso:
Alright, John. Now go right ahead.

Jon Johnson:
I got nothing. It’s fine.

Kristi Faltorusso:
Wait. You caused a whole kerfuffle.

Josh Schachter:
I got I asked your question.

Jon Johnson:
You had a really good topic, and I enjoyed listening to our guest answer your question. I was not thinking about my next question.

Kristi Faltorusso:
Okay. Caitlin, back to you. Alright. So obviously, you’ve got this underway. What’s kind of the next big boulder you’re tackling with the team?

Caitlin Wood:
Yeah. So right now, it’s all about maturing the model that we’re in and continuing to remove friction, remove seams from the customer experience. So that looks like, hey. In the old model, we had this process that worked with this system. So like something as simple as an at risk playbook. Right? Customer either raises their hand that says they’re at risk or we identify data in elsewhere that says they’re at risk. Well, what does that look like in this new model? Who takes ownership of that? Who’s, like, who owns it and then who’s supporting characters? So we’ve been completely redoing our swim lanes and kind of racing matrix of all of these things. But it’s maturing those playbooks.

Caitlin Wood:
We also, over the last six months, implemented a new CSP that we didn’t we didn’t have a CSP before. And so it’s adapting all these for new systems at the same time.

Kristi Faltorusso:
So a

Caitlin Wood:
lot of things that we’re changing and building on top of to mature out the model.

Kristi Faltorusso:
Okay. I’m gonna ask a question, and it’s probably you’re probably gonna tell me that we’re not doing it now because we’re starting simple. But Yeah. We know all risk isn’t created equal. Right? And so there’s different factors that drive different risks with our customers.

Caitlin Wood:
Yeah. Do you

Kristi Faltorusso:
take that into consideration around who owns it? Like, if it’s a a risk that is around adoption, is it CS, if it’s risk around new leadership in the organization, is the account manager, like, how do we make it?

Caitlin Wood:
Yeah. So we have different inputs here. And the way with we have designed our health scoring, it takes into account some of those human inputs that will never be platform data, and it weights them differently. And so we can design at risk playbooks and processes around depending on, like, where that input came from. And then, you know, store some of those automatically so they run for, you know, if there’s this specific risk indicator, this is what you do. Here’s your playbook to address it. But if it’s something that’s, like, multi pronged or, hey, the account manager flagged this business change, at the same time we’re seeing this user drop off and as a result this platform impact, then that’s gonna be a a kind of tiger team approach instead of who owns what.

Jon Johnson:
That’s good. I remembered my question. You’re talking about maturity.

Kristi Faltorusso:
Stop talking.

Jon Johnson:
It it actually, like, does kind of funnel into where where I’m curious about it. You’re talking about, obviously, maturity. What is back up a little bit. You mentioned that AMs handle renewal growth. CSMs aren’t Yep. Kinda handling that. How are you finding, your CSMs comfort comfort comfort level with CSQLs? Like, actually talking about revenue and opportunity and understanding opportunity and tracking opportunity for folks that maybe don’t have a renewal focus or a growth focus. Mhmm.

Jon Johnson:
Those CSMs don’t necessarily forecast outside of risk versus Mhmm. You know, whatever that is. So I’m curious how you’re empowering your CSMs who don’t necessarily have that financial conversation to be comfortable to find those opportunities. I would imagine you have some rock stars and some that, you know, still kinda need some process.

Caitlin Wood:
It’s a % a spectrum. The the way that we approached it was basically taking in in partnership with a marketing campaign, looking at, what we were what we’re pushing out for marketing and saying, okay. Well, how can we then leverage platform data

Jon Johnson:
Mhmm.

Caitlin Wood:
To identify customers who would be a great fit for this campaign? And then map out sort of what are what are based on those indicators, what are some great discovery questions that you can ask that are about how what they’re trying to achieve as a business and really lends itself well into the solutions we can provide for the campaign. So we’ve really backed into it from a place where they’re gonna be naturally more comfortable as opposed to go sell them this thing. It was much more about, like, go figure out which of your customers can benefit from this solution that will help them achieve the outcomes that they need.

Jon Johnson:
I love that. That’s great.

Kristi Faltorusso:
Alright, Caitlin. I gotta ask you a philosophical question. I’m gonna say it’s philosophical because it needs it. No. We still have too much time left before we have to get to therapy. So and I ask it this way because it might not be something that you’re doing in practice because of the way that you structured your team, but I’m interested in your thoughts because you’re talking about playbooks here. And I have I have feel I have feelings about everything going back to the therapy part of this. But I have feelings on playbooks and it providing guidance versus restrictive tasks and actions that you’re requiring the team to take.

Kristi Faltorusso:
What is your philosophy on designing a playbook to guide your team versus instruct instruct them exactly what to do?

Caitlin Wood:
Yeah. So I also have a lot of thoughts on this because we I have teams that operate in a managed service where they are measured to the second. They’re dealing with hundreds of thousands of alerts every day, and they have seconds to make a judgment. Right? And in those teams, the playbook, the SOP is it’s life. Right? Like, you have to be able to measure to it. And then when you get into these complex customer scenarios, you can’t take that same approach. You have to be able to create a sandbox and and give them basically, like, fundamental truths. So, you know, the expectation is that when you come up into a customer scenario, you come up into an escalation like you own this.

Caitlin Wood:
You’re you take ownership. You’re responsible. Even if you don’t know the answer, you communicate. So you give them frameworks and suggest, avenues that they can go down to improve those things. But the way I see those playbooks flexing is, like, at this when you’re talking about a scaled CS program and it’s digital first, you have to assume some consistency. And so those have to be more prescriptive. And then as you got upmarketed up up up in customer complexity, there’s no chance the playbook you made for customer a is gonna work for any of those 10 customers next to each other because they’re all gonna have so much different nuance. So I do think it’s a suck rope.

Kristi Faltorusso:
So Caitlin, are you saying it depends?

Caitlin Wood:
It a % depends.

Jon Johnson:
If only that was the name of our podcast.

Caitlin Wood:
Well, I mean, come on. There is no one customer success model that fits every single company. No. And There’s no right answer. It’s Yeah. You would have to use the data.

Kristi Faltorusso:
And that’s why it’s work. I wanna know your philosophy on it. Right? Because some of these things, they don’t they’re they’re not always gonna translate to practice, and what you’re designing here might be different than you’ve designed previously or what you’ll design in the future. So I’m just always curious if people’s stance on it and, like, where do you draw the lines around we’re doing these things because we need to because it’s how we’re going to manage and scale business versus this is your guidance on what you could or should be considering and what to do in the instance of x or y because we know that this is roundabout what’s gonna play out.

Caitlin Wood:
Yeah. Yeah.

Jon Johnson:
And this is why I like to start in in general with, like, what are your like, how do you think about customer success, especially from the top down. Right? Because as you start from the top, you’re right. A lot of, like, the general ideas behind it are true, and we’re gonna say the same things. It’s retention. It’s growth. It’s satisfaction. It’s opportunity. But then you start breaking it down into those five or six layers, and you start to see these vast differences.

Jon Johnson:
And one of the things that I in doing this podcast for the last two years, it’s it’s been really, like, I think, hopeful after hearing so many say, oh, CS is broken, and customer success is this, and customer sex success is that, and mentoring and coaching and everybody having these very, very different experiences.

Caitlin Wood:
Yeah.

Jon Johnson:
And then as you break it down, almost everybody that you talk to is is in a completely different industry, a completely different business. It’s like, yeah, we have this title of customer success, but what you do in customer success, that’s actually the segmentation that’s interesting. Right? Yeah. And that’s when you get into it. I I really like the way that you broke out the idea of, like, a reactionary playbook where you’ve got you’ve gotta make these decisions. Okay. Tab one, do tab two. Tab three, tab four, I’m gonna deliver.

Jon Johnson:
But then you get into that space of I think you call it a sandbox of, like, let’s just, like Yeah. Play around. Right? And let’s see what works. And I’m curious how you is that something that you you hire for when you’re looking at leaders, when you’re, like, this kind of mentality? How do you identify the type of people that are gonna kind of play in your sandbox?

Caitlin Wood:
Yeah.

Jon Johnson:
I didn’t like that.

Caitlin Wood:
There’s, like, three things that I wanna address in that question. Yes. Because there there were there were questions throughout,

Kristi Faltorusso:
and so I wanna address

Jon Johnson:
good at asking 10 questions. And then

Caitlin Wood:
in one?

Kristi Faltorusso:
That’s why I have to stop him and inject my own questions at some point because he cheats and asks 10 at a time.

Caitlin Wood:
Yeah. Well, so one thing I wanna say before I get into hiring and and how I how I think about hiring philosophy and role philosophy is you also have to think about the context of when you’re rolling all based in that. Yeah. So in a year where we just had so much change going on, people’s capacity to operate within a sandbox as opposed to operate within a playbook is different. Yeah. Like, if I’m rolling out 20 changes at a time, I can’t expect my entire team to take the right action all the time without at least an example. Right? Like, we can’t do it all. They they can’t they can’t process all of that at the same time.

Caitlin Wood:
So there’s you have to communicate more than you would if it was the only change you were rolling out.

Jon Johnson:
Yeah.

Caitlin Wood:
So I do think that’s also part of it. But going into who I hire, my hiring philosophy is always attitude, aptitude, experience, and order. And so whenever I’ve messed with that order, I’ve I’ve learned this lesson I wish I could start learning this lesson. You know what I mean? Like, every time I I ignore my gut on that, something goes wrong. And so, attitude, then aptitude, then experience. And I’m always looking for people that, are showing me that they’re really interested in the problems we’re trying to solve, and that want to they’re gonna get creative and help us adapt because we’ve grown so much, we’ve changed so much, like it’s not going to stay static. And so they have to be people that are comfortable asking questions. It’s it’s best idea wins.

Caitlin Wood:
And so, you know, it’s a lot of it’s a lot of culture fit and a lot of, like, can you can you have can you dig in on some of these topics? I also am very preferential to doers instead of doers. Like, you gotta be able to get in a room and, like, let’s workshop through this as opposed to just talk it out at a high level.

Kristi Faltorusso:
Okay. Then I got I have to how do you interview for a doer versus talker?

Jon Johnson:
Raising our hands for the

Kristi Faltorusso:
audio So I had to I had to

Jon Johnson:
Christy just

Kristi Faltorusso:
raised John, I had to before you jumped in and asked something, I wanted it to be known that I had a follow-up question to your point.

Jon Johnson:
Yes. Christy, you and your friend, do you have a question?

Kristi Faltorusso:
Bueller. Bueller. Caitlin, how do you hire for this?

Caitlin Wood:
Yeah. A lot of it is is, like, give me an example of this. Talk me through actually what you did and and how you got there. So I will often one of the questions I had a former, colleague that gave me this interview question years ago is, like, one of the best interview questions ever. It’s tell me an achievement that you’re in your career that you’re most proud of. And then depending on the answer to that, you kind of get a sense of, like, of what what role and what responsibilities they had and how big they were thinking. And then once they give you that answer, it’s a it I start to well, okay. Walk me through how you got there.

Caitlin Wood:
Like, what did you do? Who did you work with? Was this you? Was it, like, actually, process wise, how did you get to that end result? And that gives me a better sense.

Jon Johnson:
That’s good. I mean, I think that’s it. You answered all of it.

Kristi Faltorusso:
I mean, probably not.

Jon Johnson:
No. I know. But Josh is gonna start

Kristi Faltorusso:
I I gave you a I know John’s gonna get Josh is gonna get all fluffy in a second. Hold on. And he’s gonna come in here and start opening doors and shutting down microphones. Galen, before before we do start to work towards concluding this episode,

Jon Johnson:
how

Kristi Faltorusso:
are you thinking about the inclusion of AI in your world right now? Now I know I know, again, you’re starting simple, and you’ve already disrupted the universe. But I I know that AI is a topic of conversation because the the VCs and PE firms all across the the world are mandating that as leaders, we consider this. What role is it playing and how you’re architecting the team moving forward now?

Caitlin Wood:
Yeah. Well, if you hadn’t have brought up AI, what I would have said is if I don’t say AI, like, I’ve answered the question wrong. Right? Because it’s I’m really sorry. So the way that we’re thinking about AI is is is a few different capacities. So our platform, like, actually, how we’re delivering information for our customers, we are absolutely leveraging AI today. We’ve used it to make our teams and services more efficient. We’ve used it to make, information that we deliver better and more contextualized, which is awesome. So given our customers’ core value there.

Caitlin Wood:
We’re using it within our productivity tool. So we’re using, within our tech stack via, AI powered, search interface for our customers. So allowing them to get information faster. I see AI as as helping us to drive more self-service options, more service, make it easier for customers to manage their platform. The thing about cybersecurity and cybersecurity to us is like, it’s not a configure the platform and then let it run. It’s continuously adapting to what threat actors are doing because they’re changing all the time. So you have to keep up with it and which can lead to configuration gaps. It can lead to, you know, if things get out of sync, then you might miss something.

Caitlin Wood:
And so there are a lot of practical applications for how we’re gonna make customer experience better with AI. We’re using it today in in, you know, task creation and task follow-up and those sorts of productivity tools. So kind of both internally and externally. But the thing about leveraging AI across customer success is you have to remember that every single part of an organization is responsible for customer success. Mhmm. Like, you can’t deploy AI to customer success to make your customer experience better if you don’t have great connectivity into your product team, into your marketing team, into the enablement, if you your knowledge center isn’t up to date. Like, AI doesn’t magically solve a broken foundation. It’s gonna put a spotlight on it.

Caitlin Wood:
And so you’ve gotta have all those ducks in a row and be really approaching this holistically as opposed to just, you know, CS is gonna deploy AI, it’s gonna fix all the issues. Like, it’s the tip of the spear. But unless you’re working together as a whole organization, you’re not gonna get

Jon Johnson:
that. That’s good.

Caitlin Wood:
So that’s good.

Kristi Faltorusso:
So now I have exhausted all of my questions, John. But I feel like if we did

Jon Johnson:
so happy

Kristi Faltorusso:
at the beginning the AI routes that we would have had a complete missed opportunity. And I won’t even get into all the other questions I have, Caitlin, because now I’m like, well, what happens to your team? And do do you have too many people? Because now you have AI, and it’s making your data more. Because we’re like, I I’m not gonna go there. So, John, what other questions do you have for Caitlin?

Josh Schachter:
No. Listen. I have a question here. My my question is forget it. I wanna go back to Josh.

Kristi Faltorusso:
Yeah.

Josh Schachter:
Here we go. Back. He’s back. I wanna go back to how do you identify a a big talker versus an actual doer in an interview? Because that’s just

Jon Johnson:
oh, man. If I could if

Josh Schachter:
I could figure that one out. I know you gave an answer, but, like, but, really, how

Jon Johnson:
do you do that? Yeah. But

Josh Schachter:
if you

Jon Johnson:
could figure that out, Josh, you wouldn’t have two podcasts.

Kristi Faltorusso:
I was gonna say, and and Josh wouldn’t actually have a job. Well, that’s why Josh is the CEO because everyone figured out that he’s a talker and not a doer, so he had to hire himself.

Josh Schachter:
Is that a compliment? I

Kristi Faltorusso:
think that’s how we end. I think that’s great.

Josh Schachter:
Bye, guys.

Jon Johnson:
I don’t know how I feel about it. For Steve. No. But, Caitlin, thank you so much, for the time. We appreciate it. Oh, we’re still record Josh, I thought you stopped recording. Hi, guys. You’re still listening to this.